Posts Tagged New York
Movie, No Booty
Posted by One Gay at a Time in Gay Dating on November 28, 2011
If having to work on a Sunday isn’t bad enough, following a night of heavy drinking only makes things worse. My coworkers noticed my less than human state and offered to get me things to ease my pain, but I explained I just wanted to finish work and go back to bed.
The day was long and arduous. Many of my coworkers were dragging their feet, and it was all I could do to light a fire under their asses. I was trying to be as time efficient as possible, but it was no use unless everyone else was onboard.
When I didn’t think my day could get any worse, my mother called to tell me my grandfather passed away. I was expecting the news, but I had no idea when the call would come. He had very advanced cancer, so it was only a matter of time. I know he was more than ready to go, at times basically asking the hospital to give him the “black pill,” but no one likes to see a loved one go.
I soldiered on through my day not mentioning it to anyone until I was about to leave. I needed to tell my boss I would out at the end of the week to go home for the funeral. He was very sympathetic and supportive.
Really, after such a long day at the office, I wanted nothing more than to see Smiles. He could make me happy, no matter what physical state I was in. I hadn’t seen him since Friday night, and I didn’t get to spend the night in his apartment. I was itching for more time with him.
When I was nearing the end of my workday, I texted Smiles to ask him if he wanted to grab dinner. After some time passed, he responded apologizing, “Ah shoot! Just seeing this now. I ordered pizza and I’m starring at the mess I have to clean up here.” I was a little disappointed, but I wasn’t giving up that easily.
“Mind a little company for an hour or so? Not going to be around this week really…” I texted. We had a very big pitch coming up that week, and I knew I would be working late most nights. This was my last stitch effort to see him for a while. He replied, “Come eat this pizza and hang out. It’s not like the mess is going to get any worse.”
This was my first time venturing to his apartment. I knew the general neighborhood, but not the exact location. After work, I took a cab to his apartment. I was very excited to see him and happy I was finally getting the invite to his place, even if I had to invite myself.
His apartment was not what I expected other than the mess he was describing. He was in the process of moving and office worth of things into a storage unit. I didn’t care about any of that. I just wanted to cuddle up next to him in bed.
He offered me pizza, but I explained I already ate. He suggested we watch a movie, and I agreed. We went into his bedroom and chatted while he picked a movie. I told him about my grandfather, and he lent me his sympathetic ear. We’d already talked about how he was ready to go when we discussed religion at his birthday lunch, so he was already quite versed in the situation.
In the meantime, he selected All Good Things while I snuggled up next to him. I have a thing with constantly petting guys I date. I don’t know why, but I just crave the physical connection. I was constantly stroking him gently with my finger tips throughout the movie, switching my hand positions periodically. It was all I could do to refrain from jumping his bones. It wasn’t the most romantic movie of the year, but I’d already seen it and had sex on the brain. It’d been a while since we last had sex, and I wanted more.
Sadly, that wouldn’t happen once again. When the movie ended, it was 11:00pm. He gently hinted at my departure, even going to the bathroom to brush his teeth. Yet another sexless night. I was really beginning to wonder why he didn’t want to have sex with me. I wondered if it was my issues coming between us or if he wasn’t attracted to me. He never gave me any compliments about my body even thought I made a point of complimenting his. Maybe he just didn’t find me attractive.
Regardless, I gave him a kiss goodnight and walked all the way back to the PATH station to head back to Hoboken. The whole walk, thoughts flew through my head like lightning. I was hurt and worried. Hard to admit, but I almost wanted to cry.
That wouldn’t be the worst part of my night however. In the middle of the night I was woken by violent stomach cramps. I ran to the bathroom and destroyed my toilet. At times, I had to debate which end was more priority to face the toilet. I got almost no sleep and had a full day of work ahead of me. There was no way I could take a sick day.
In the morning I was greeted with a text from Smiles: “Maybe a stomach flu? Up all night with cramps and still hurting 😦 .” I finally nailed the source. I caught some bug from him. “I shared your pain! Still sharing… Was trying to figure out what I could have eaten yesterday… And I have to work all day today… 😦 ,” I responded. To which he replied, “This is the worst!”
Karma was coming back at me something fierce. I don’t know who I p*ssed off royally to deserve such a bad weekend, but the only thing keeping me going was it couldn’t get any worse than it already was.
Follow @onegayatatimeEvery One But the One I Want
Posted by One Gay at a Time in Gay Dating on November 22, 2011
Friday arrived, and I was starting to nail down plans with Smiles for the night. He had things to do all day, so we planned to grab dinner and then head to his friend’s birthday party.
This meant I had time to kill after work. My good friend A asked me to grab happy hour drinks with her. She recently moved our of Hoboken into the city with her boyfriend, so I was already seeing a lot less of her. We were due for a catch-up.
She picked a place in the Flatiron District that’s known for their happy hour. We cozied up to a spot at the bar and chatted about our new situations. It had been a while since I caught her up on the status between Smiles and I. I took her for a ride on the roller-coaster ride of emotions I’d been through. She gave me advice on how I should proceed and things I should watch out for. After five years, she knows me quite well and can predict a lot about me, so I’ve come to listen intently to what she says.
She also took the time to talk about the new challenges she faced moving in with her boyfriend. I tried to give her my two cents for what it was worth. My biggest advice to her was to pick her battles. On the things she could let go, she should, but on the things she really cared about, she should make a stink. That way, he would realize with more poignancy when he was doing things that got under her skin.
In the middle of our conversation, Smiles called to discuss dinner. He chose a place about two blocks from where we were drinking, and we agreed to meet in a half hour. When the time came, and A and I had our fill of cocktails, we walked to the restaurant Smiles chose. I coerced her into coming along to meet him since none of my friends had the opportunity yet.
I introduced them to each other, and Smiles invited her to join us for dinner. A had plans to meet her boyfriend for dinner, and I could tell she was looking for a quick exit, so she agreed to sit with us for a few minutes. She was already running late. I appreciated her making the extra effort, and gave her the out she needed. I told her to get on her way.
After she left, the conversation with Smiles was slightly forced and awkward. I was having a hard time breaking through and there were periods of silence. I learned he was feeling very sick and his stomach was bothering him. He had issues with his appendix, and it was inflamed and bothering him again.
Now, I was worried. I genuinely cared for him and my paternal instincts kicked in. I was worried for his safety and said, “Don’t be a hero on me here. If you aren’t feeling well, we can go at any time. Don’t soldier on on my account.”
“Thank you for your concern, but I’ll be fine,” he replied.
The rest of the meal was pleasant, but quiet. I reached my hand under the table to rub his knee to try to make a better connection while we chatted. That, and I was still worried about his condition.
When we finished dinner and desert, we had some time to kill. Smiles walked around the neighborhood looking for a massage parlor (legit, not sexual) in which to kill time before the birthday party. We couldn’t find one still open to take advantage of, so we hopped in a cab and made our way to the party.
When we arrived at the party, I was slightly overwhelmed by the crowd. I’d never been to a party so heavily skewed male in my life. I learned the birthday boy was gay, which answered a lot of questions for me.
We found a comfortable spot to plant ourselves and each grabbed a drink and something to nosh on. We made a friend and chatted with him a bit. He was an extremely jacked and cut black man who is an interior decorator. It was interesting hearing him talk about his occupation, all while looking at someone who looked like a personal trainer.
After some time, this man turned to us and said, “Oh. Are you two together?”
Both their eyes focused on me. The pressure was on. I didn’t know what answer Smiles was looking for, but I saw this as an opportunity to gauge his reaction. I tilted my head slightly to the side nodding and said, “Yeah.”
Our new friend called attention to and questioned my head tilt heavily. I pointed out we didn’t know each other all that long. I still look back and wonder if Smiles was actually looking for me to say yes. I still wonder if he was being distant because he thought I wasn’t fully invested in our budding relationship. Of course I wanted to say yes, we were dating, but I didn’t know where his head was at the time. I didn’t want to scare him off by being overzealous.
We were nearing the time to head out for the night, but I needed to use the facilities first. That was particularly a challenge because the bathroom was being used by a few to sign a birthday book photo album. Finally, I gave up and assumed I could go when I got back to Smiles’ apartment.
We went downstairs and hopped in a shared cab with one of the female guests from the party. As we progressed, I learned I would not be going back to Smiles’ apartment. My destination was the PATH to go home. I was slightly shocked and annoyed. It was a Friday night. Why wasn’t I being invited back to his place. I know I’d never been there before, but this was a bit ridiculous. It was around midnight, and I was dreading my trek back to Hoboken.
He hopped out of the cab with me. We said goodbye on the street with a quick kiss, and I was on my way home. I’m not gonna lie. I was hurt. I felt rejected. There was only so much rejection I could take.
As I walked, I pulled out my phone. I called Boston, but of course, he was still ignoring my calls. I left him yet another voicemail. I also called my new friend to see what he’s been up to. No answer either. Finally, I texted the Principal. It’d been a while since we chatted, so I thought I’d given him enough space. We began texting, but I told him I’d have to continue the conversation on the other side of the river.
While waiting for the PATH, I nearly p*ssed my pants. The train going into the city dropped off a tranny who felt the need to flirtatiously wave at me and say hi. When it finally arrived, I leaned my back against the wall and closed me eyes to concentrate on something other than my bladder. Two women were in front of me on the crowded train, and around a turn, one fell into me. They started arguing with each other and engaged me in conversation. Though not stated outright, I learned they were a lesbian couple, and they were hot. We had a long conversation, and when we arrived at the Hoboken stop, they invited me to come hang out with them. They had no idea my preferences fall in the men category, and they were inviting me back to their place. I used my bladder as an excuse and said goodbye. It was early enough, but I was not in the mood to play.
While speed walking home, a very large black girl grabbed my arm, pulled me towards her, and shouted, “TAKE ME HOME WITH YOU!” I ripped my arm free and continued to walk home, all the while texting with the Principal. I was flirting slightly, but not to the point of crossing the line with him. I missed talking to him and our flirtations. I really did like the guy, but the distance was still killer.
When I got home, I relieved myself and hopped into bed. I was disappointed I was there alone, but I opened up a whole new can of worms with the Principal. He still wasn’t over me, and I just scratched open that scab again. I even went as far as to pull up Grindr again for the first time in over a month.
It was just my luck. The one I wanted to be spending my night with just sent me on my way, while everyone I didn’t want anything to do with seemed interested in me.
Furthermore, I wouldn’t be seeing Smiles the following day. Originally I was planning to go to a horse race in New Jersey and invited him to join. When the day was approaching I was no longer interested in going and sold my ticket. I was hoping to spend the day with Smiles, but I learned he was going to Six Flags with friends — without me. I understand he has a life of his own, and I don’t have to spend every waking moment with him. But at this stage in our relationship, I wanted to spend more and more time with him. I certainly would have invited him on a fun trip such as the one he was going on. Apparently, he didn’t feel as strongly for me. A clearer picture was being painted for me. Maybe he just wasn’t that into me.
I realized things weren’t going as smooth as I would have liked, so I set myself on entertaining other ideas…
Follow @onegayatatimePlaying It Cool
Posted by One Gay at a Time in Gay Dating on November 21, 2011
My weekend with Smiles was a decent one. I’m not self-destructive, nor do I get in my own way enough to think it was a failure or a bad weekend. Any time I spendt with him was progress, and it made me happy. But, I left the weekend feeling a little uneasy. I was denied twice in two days. Did he not find me attractive? Was he just thinking of me as a friend? Not knowing where I stood was eating away at me.
It’s obvious he was interested in me. But, it was his level of interest that worried me. We were in the beginnings of a budding relationship, or so I hoped. Things were supposed to be carefree and fun. The heavy stuff comes later. We should have been having sex like rabbits and dying to see each other.
I felt like I was constantly chasing after him. I got no indication he was interested in chasing me. But, maybe I wasn’t giving him the opportunity. Maybe I got so excited about him, I was constantly initiating our time together, and if given the chance, he would be asking me out on dates.
On Monday evening I texted him to see if I could spice things up with a little getaway. “Hey. What would you say to getting out of the city for a weekend?… Celebrate your birthday, just the 2 of us… Something totally low-key and relaxing like New Paltz, NY. Gorgeous this time of year too and not that far…” I thought if we hit up a bed and breakfast, we could find the time to get wrapped up in each other with no other distractions.
A big part of me thought this was a giant leap forward, and I was moving too soon, but another part of me noticed a little bit of stagnation. Things were getting a little stale. Maybe I needed to intervene to get us to that happy-go-lucky mindset.
Just as I expected, he safely replied, “Hmmm that sounds like fun, can I think on that one for a min? I’d want to be able to give you my full attention and I think with [work] this weekend, the [possibility of a new prospective work project] starting and the over two jobs with a bit of clock on them, I might not be totally present. Which wouldn’t be fair.”
I was right. Too soon, too fast. I didn’t want to cower and backtrack. I had to play it cool. “Certainly. Wasn’t exactly talking about this weekend. Was more thinking 3+ weekend out. Just wanted to throw it out on your radar,” I replied. I wasn’t lying. I was really just planning in advance.
He got my drift. I soon got a text back: “Ah. Ok. Sleep well. I’m crashing early tonight for a change.”
I decided to take some advice from friends and play a little hard to get. I stopped texting or calling. The next point of contact was going to be initiated by him. It killed me. I wanted to text so bad. I never went anywhere without my phone, waiting for him to text or call.
Tuesday went by without a word. I was in a bad place. I started having doubts about the whole thing. We were only a couple of weeks in, and he already grew tired of me. These weren’t good signs, and I started to really get down about it.
I decided, I wasn’t going to put myself back out there completely, but I was going to continue to put my ear to the ground to see what was going on out there. I started answering my messaged on OKCupid and chatting with a few guys. It was nothing crossing the line, but in a way, I was laying some groundwork if Smiles decided he was done with me.
Finally, on Wednesday, he texted me to ask me how my day was going. The exchange went back and forth a bit before simmering out. I was thrilled — Back on top. I recognized how happy I was, but I also recognized how dependent I am on others for my own happiness. This is an issue. I really need to learn to be more independent. It’s not healthy to need other people to that extent.
In our exchange, he invited me to come with him to a bar to watch a friend’s band the following night. I reminded him I had volleyball on Thursdays and couldn’t go. I really wanted to go, but another part of me was happy I had to turn him down. I have a tendency to drop everything for men I’m interested in. I needed to show I was independent as well.
Thursday went by, and we didn’t talk to each other during the day. On my way to volleyball, I texted him: “Thinkin’ bout you 🙂 .” He responded, “Good luck at your game!” It was nice he remembered I had a game. He was showing a vested interest in my life, which is always a good sign.
After volleyball, we texted a bit. He told me about how he didn’t get the project he was counting on for work. I knew it meant a lot to him, so I tried to console him as best I could. I knew he would be depressed for a few days as a result because he was really looking forward to it. I called him, and we spoke on the phone. I also took the opportunity to ask if I would get to see him Friday night.
Since he asked me to watch the band with him, I was satisfied he wanted to spend time with me, and I knew it wasn’t simply me chasing him down.
He had plans to go to a friend’s birthday party Friday night and talked about us going together as if we planned this long ago, and it was assumed I would be attending with him.
It appeared things were back on the upswing, at least emotionally for me. The question remained. Would we continue moving up, or was it only a matter of time before things started sinking again?…
Follow @onegayatatimeFillet Mignon and Baked Potatoes
Posted by One Gay at a Time in Gay Dating on November 18, 2011
After breakfast at the hotel, we got back on the road to my great-aunt’s house in Mount Vernon to drop off the keys and make our way home. It was surprisingly fast.
I was really disappointed I never got to chat much with the bride. It’d been years since I’d last seen her, and we only speak on the phone about once every four or five months.
During the whole ride, I had a lot of time to think. For me, this is deadly. When I have time to think, I crawl up into my own head and start digging around where I shouldn’t be digging — This is why I lead such an active lifestyle. Thinking depresses me.
A lot of thoughts about Smiles were going through my head. I was a little hurt and upset my advances were rejected in the morning. I also was very disappointed I didn’t get to grab brunch with him. Overall, I guess you could technically deem the weekend with him a success, but I still wasn’t thrilled. I was on unstable ground. I had no idea where I stood with him, and it was getting to me. As usual, I was over-thinking everything.
When we got back to Hoboken, we stopped at the grocery store. I decided to call Smiles to see if he wanted to come over that night. I wanted to make him a nice home-cooked meal since he never cooks for himself. We always go out for dinner or order take-out. He agreed to come by. I also had ulterior motives. I wanted make-up sex for Saturday morning when I was denied.
That evening, when he got off the PATH, I hopped on the motorcycle and rode down to pick him up. I was happy to finally get him out on the bike. He’d been on one before, so it wasn’t as exciting as the first time I’d taken motorcycle virgins on the bike, but it was nice to have him so close to me. We rode back to my apartment with his arms tightly around me. I thoroughly enjoyed it.
I started us off with some artichokes while the fillets finished grilling and the rest of the meal finished cooking. I made more food than the two of us could possibly finish. When we had our fill, I cleaned up, and we made our way to my bedroom for the night. He asked if he’d be spending the night. “Of course you’re spending the night! Did you think I was going to kick you out now?” I responded. “I don’t know. Some people need their rest before Monday morning,” he said. I reminded him the size of the California king bed and assured him he wouldn’t disturb my slumber. If anything, he would enhance it.
Warning: The following may be too graphic for some. I started getting frisky. After not getting any the morning before, I was even more geared up for some great sex. We undressed each other and jockeyed for position once again. I wasn’t making the same mistake again. I made sure I was in position to top this time. When I pulled out my night-stand drawer to get a condom and some lube, he made a comment about the large dinner and not sure it was a good idea. I surrendered, and we decided to use alternate methods. He climbed on top and used his hand behind his back. I was impressed with his ingenuity and his willingness to try alternate methods. However, it wasn’t quite enough for me. It felt great, but I couldn’t quite get over the final hump, as is my issue often.
We stopped and just enjoyed each other’s bodies laying next to each other before we both cleaned up and hopped into bed.
When I woke in the morning, I snuck quietly into my bathroom to shower so he could fall back asleep. If he wanted, I was going to let him sleep as long as he wished and just pull the door shut behind him. However, he had a few things he wanted to get to Monday morning, so he joined me on my morning commute.
We casually walked to the PATH and hopped on. When the time came for him to get off, we exchanged a quick kiss. A lot was going through my mind before that. I was a little afraid to do it because I knew all eyes would be on me as soon as he got off. However, I was the one who initiated it. It was subconscious, but I wasn’t going to let fear of others’ reactions rule my actions anymore. I didn’t care who knew I was gay anymore.
I rode the rest of the way to work not making eye contact with others. I wasn’t 100% comfortable in my own skin, but I was still growing with every day. Things were progressing nicely with Smiles, and they could only get better with added confidence.
Follow @onegayatatimeThe Wedding Roommate Date
Posted by One Gay at a Time in Gay Dating on November 17, 2011
After Smiles left for New York to return the rental car with the two other girls from the screening, I sat around waiting for my roommate to wake up. When I got bored with that, I hopped in the shower, repacked my bags and laid everything out to get ready for the wedding. The night before, I promised her I wouldn’t wake her before 10:30. Obviously, all that didn’t take and hour and a half.
Finally, the time came to wake her. I sat impatiently while she got ready. She suggested we go eat and come back to get ready for the wedding. I agreed. However, when we couldn’t find a place to get brunch for about 45 minutes, we gave up and decided to go back to the house to get ready. We would grab breakfast at the first decent place we passed on the way to the wedding.
I was ready in about 10 minutes and had to wait another 40 minutes until she finished getting ready. WOMEN! This always makes me realize part of the reason why I’m gay! I’m sure my straight male readers can relate to me on this one!
We found a nice place to grab some great coffee and breakfast sandwiches. It was owned by a brother and sister pair far older than I. At one point, while talking to the gentleman in the booth behind us, they started to bicker. I put my head down and began to chuckle to myself. “Excuse me sir! I don’t think this is very funny,” the sister said towards me in a semi-joking tone. Now, I was laughing blatantly. “What’s so funny?” she asked. I explained my relationship with my older sister and how I could easily relate to the brother. I immediately was on her bad side, but I could tell deep down she really liked me — It was all an act. Everyone was eying us up ever since we walked in the door. I was wearing a dapper suit and my roommate had on a hot dress. There was no way to simply blend in now.
We finished our breakfast, we made our way for the door. The sister made a point of making eye contact with me and giving me a dirty look, but the brother also made a point to wish us a pleasant day.
Once we got back on the road, I was reminded once again how bad a driver my roommate is. She was all over the road and scaring the crap out of me. In fact, as we approached a cop on the side of the road, she veered off the road once again.
We got to the hotel and settled in. As we checked in, I noticed a guy in a tux (who I would later find to be the groom) who resembled me. I pointed him out to my roommate and she agreed. When the time came, we made our way to the church. We barely made it in time. We were actually running from the car.
After the wedding, my roommate and I walked downtown to take a few photos and buy some chocolates for my great-aunt. We had a lot of fun.
We made our way back to the hotel to hang out at the bar with my friends from college before we hopped on the bus to the reception. While closing my tab, the uncle of the bride asked me if I was a relative. I was a little perplexed since he was a relative. He should know if I was family. Then I realized there were two families coming together that day. I told him I swam with the bride in college. “Oh. You look a lot like the groom — Like you could be his brother or something,” said this man. I laughed and said I noticed the resemblance as well.
At the wedding reception, I really came to appreciate my roommate. As a gay man, I have limited resources for a wedding date since I wasn’t in a relationship. I planned to go with another female teammate who is still a great friend, but she went and got pregnant on me so she couldn’t travel. I floated the idea to my roommate to be my date months prior, and she jumped on the opportunity. She went to the same college as the bride and I, so I knew she’d fit right in.
I witnessed another friend from college sitting at our table arrive to the wedding and the reception stag. We had quasi dated in college for a very short period. The bride actually tried to set us up. She was the only single person at our table (I’m not exactly sure how you get a table with an uneven number). I felt really bad for her, but I was also very happy I didn’t show up stag myself.
I got myself nice and lubricated with about half a bottle of scotch and had a blast the rest of the night. The only time my roommate and I weren’t on the dance floor was to walk outside so we would stop sweating. Then, we’d make our way right back to the floor. The girl who came alone even came up to my roommate and made a comment about how lucky she was to have such a great wedding date (or so I was told later by my roommate). I had so much fun at this wedding – The most fun I’d had at any wedding I’d been to before. This is all for one reason. I had a great date! It makes all the difference. Who’d have thought taking your roommate to a wedding could be so much fun?
After the reception, we went back to the hotel bar to hang out some more. The problem was, all my friends left, and my roommate and I were exhausted. Half an hour passed, and the bride was nowhere in sight. While we waited, I took the opportunity to text Smiles: “Sooooo much fun! Missing you!” We were ready to give up and go to bed, but not before we raided the cereal bar for a late night snack in our room.
In the morning, we went down for the complimentary breakfast in hopes of seeing the bride again. I learned she wasn’t coming down because they had to get on with their honeymoon plans. I also learned I missed her last night at the bar, had I only stayed a little longer. I also received a text while we ate from Smiles. “Morning! Glad you guys had fun. I wish I could have spent the afternoon out there with you!” It was a very nice sentiment, and it brightened my day a little.
With that, we took coffee to go and got back on the road home…
Follow @onegayatatimeYou’re an Actor Too?
Posted by One Gay at a Time in Gay Dating on November 16, 2011
I had been scheming for weeks, ever since I found out Smiles was screening his movie in the Hamptons in conjunction with the annual film festival. I finally had my answer – He wanted me there.
I had a wedding on Long Island the following day, so it was convenient for me to head out there early to catch his film. I hadn’t seen it yet, so I was very curious.
Since I already booked a hotel for the wedding, I wasn’t exactly thrilled about dropping more money on another hotel room (if I could even get one with the festival). Then I had a brilliant idea. My great-aunt has a house out in the Hamptons. I emailed my cousin and asked her if she thought I could use her mother’s house for a night. I wasn’t looking to make a whole weekend of it. We literally just needed beds to sleep in and showers in to use in the morning. Luckily, my great-aunt obliged. I asked Smiles if he’d like to stay with us, but I didn’t get a straight answer. He was trying to find something closer to the screening.
My roommate was my date for the wedding (sad, I know, but this is the life you lead when you’re gay and single). I ran my plan by her, and she was down for it all. I left work early Friday, went to Hoboken to picked up her car and our bags, drove back into the city, and pick her up when she finished work. After that, we headed up to Mount Vernon to hit up my great-aunt’s house to get the keys.
Of course, this took forever! We got turned around twice and had to deal with Friday evening city traffic. I was starting to fear missing the beginning of the screening. When we finally arrived at the house to get the keys, I couldn’t just grab the keys and run. I hadn’t seen my great aunt since the funeral of my grandmother, and it had been years before that since we last saw each other. I knew I would have to sit and chat a bit. She was thrilled someone was getting use of the house and gave me long instructions on everything. Luckily, she is still sharp as a tack and after a short chat, she suggested we get on the road quickly so we didn’t have to sit in too much traffic.
We made our way across almost the entire length of Long Island before finally arriving at the bowling alley the film was screened at. We didn’t even stop to grab dinner, so I was praying this place had some decent food.
We walked inside and were greeted by Smiles. He and his crew were getting set for a round of bowling. My roommate and I took over the lane next to them to bowl a game or two before the film. Apparently, we made excellent time and even had some to spare (Get it? Bowling… Spare…).
Smiles looked very smart and was being decently affectionate. I wasn’t sure how the night was going to play out. I had a feeling it may be slightly awkward, but I wanted to be supportive. I talked to him before heading out there to see what the situation would be. I asked, “Will you be working the whole time, or is it more relaxed than that.” He explained he would get to spend time with me, and it would be worth it for me to come since I was already heading out in that direction.
While we were bowling, the alley owner’s teenage boy was hanging out with Smiles and his crew. He’d been with them all day hanging flyers around town. At one point, he made a comment to Smiles about his wife coming to the screening. Smiles told him he wasn’t married, and the kid immediately questioned himself and said, “Or girlfriend?” When Smiles shook his head, the kid replied, “Oh, or boyfriend or whatever.” Smiles simply replied, “Well… Him,” and pointed at me. I didn’t notice this happening, but Smiles made it a point to come over and recount the story for me.
The time came for the crew to start getting set up for the movie. My roommate and I finished our game and hit up the bar to grab some drinks and grub. From across the room, I watched Smiles greet some of his friends and chat with them a bit. When he finished, he came over to check on me and grab a beverage. He mentioned his friends and their names. When he said one name in particular, my ears perked up. It was his ex. I was very curious how that would play out since I know they are still close, but rarely get to see each other. He told us to grab seats since the movie would be starting soon, so we made our way over to the chairs and grabbed a spot.
When he sat down, he sat with his other friends. I wasn’t jealous. I knew he didn’t get to see them much, so I would take a backseat on this one (however, a small part of me was very disappointed after driving over four hours to see this). I watched the movie intently, but I have to say, I did glance at Smiles and his ex in front of me to see the body language happening. Again, we weren’t in a relationship yet. We weren’t even dating yet. We were just seeing each other, or at least in my mind that’s how it was defined.
Part of the way into the film, I was shocked to see Smiles on the screen. I knew he was a producer of the film, but I had no idea he was acting in it as well. I was very proud of him and the great job he did. The film was great and surpassed my expectations — Totally an indie film I’d rent at Blockbuster, not some NYU student project.
After the film, my roommate and I made our way back to a spot at the bar to grab another drink. After chatting with his friends some more, he came over to me, apologized to my roommate and asked for permission to steal me away to introduce me to them. I’m sure my face lit up like a Christmas tree. He was acknowledging me to his friends. FINALLY! It was the validation I was looking for after the birthday party.
However, when one of the friends asked how we met, Smiles turned to me. My head immediately went to Grindr and how I didn’t want to say that. I could have said we met through a mutual friend, but I said, “I’m going to default to you on this one,” and turned to Smiles. He paused a minute and replied, “We’ve gone out to dinner a few times back in the city.” It was interesting to see him struggle with the answer as much as I had. After a short while, the friends had to be on their way. A band was beginning to play, so I called my roommate over and stood by her with Smiles and some of his crew. Later in the night, I learned the man I thought was his ex simply share the same name as his true ex. I felt a little more relaxed for some reason.
Periodically we showed signs of affection towards each other, such as a subtle hand hold or a glance. It was nice. It was still nerve-wracking because I didn’t know what he was comfortable with yet. We weren’t defined, so I wanted to make sure I didn’t overwhelm. That happened in the past, and I didn’t want it to happen again.
Smiles directed me to speak with the director of the film. She and her friend wanted to know if they could crash at the house for the night as well. This was the first conformation I received of Smiles coming as well. Until then, he hadn’t given me a definitive answer. I explained to the two girls, I hadn’t been to the house before and wasn’t sure of the bed situation. However, they were more than welcome to join the adventure. When the band finished, we made our way to my great aunt’s house.
The drive was nice and cut through some cute towns. When we arrived, Smiles said, “Do the Bouviers live here?” in a reference to Grey Gardens. The exterior of the house didn’t look to be in great shape. I was a little worried. When we got inside, I was pleasantly surprised to find the house in more than decent shape. It was very large and slept about sixteen comfortably. All the girls got their own rooms if they so chose. Smiles and I would be taking the master downstairs of course.
We immediately settled in. We talked a bit, and I came to find out he wouldn’t be able to grab brunch with us in the morning. He had to get the rental car back to the city by noon. I was very disappointed. Everything I planned so far had worked out perfectly. The screening. The house. My plan to make it a quick little getaway with him was failing. After brushing our teeth, we climbed into bed and cuddled a bit until we dozed off.
When we woke around 9am, I tried to get a little frisky. I reached my hand down and gently began to try to excite him until I was gently pushed away and told he was exhausted. I admitted defeat and disappointingly went back to just laying next to him. Me ego was a little bruised.
Shortly following, we both got out of bed, and he got dressed and packed up to go. I said goodbye to the bunch and tried to find something to entertain myself until my roommate woke up…
Follow @onegayatatimeBirthday Lunch
Posted by One Gay at a Time in Gay Dating on November 15, 2011
The official day arrived. Smiles was turning 36. He celebrated his birthday in conjunction with two friends a week earlier, which didn’t go so well for me. I wanted to rectify that situation.
I also wanted to dote on my new man for his birthday. I called him early in the afternoon to wish him a happy birthday and ask if I could take him out to lunch. The Ace Hotel is near my office and has two great restaurants and a bar adjoining it. Normally I’d let him choose, but I couldn’t wander too far from work on my lunch break.
I met him not far from the hotel on the street corner. I greeted him with a big ol’ kiss and a hug to say happy birthday. As we walked, he made comments about how casual my work attire was. He was under the impression people in advertising walked around in Mad Men suits all day. I explained how far off base he actually was.
As we walked, he reached down for my hand. I love it when he does that! We arrived at the first restaurant he chose, and after checking out the menus at John Dory, we decided to leave and hit up the other, The Breslin. I’d been there many times and absolutely love their lamb burger. I knew he’d be happier with the choice as well.
When the waiter asked if we’d like anything to drink, I declined, but encouraged Smiles to order a drink. He requested a dark and stormy. Without looking at the menu, I immediately knew what I wanted, and ironically enough, we both ordered the lamb burger. I also added another dark and stormy to the tab after seeing how refreshing his looked. Afterall, I work in advertising… It’s only natural to have a cocktail lunch, right?
Somehow the topic of conversation turned to religion. My mother was just telling me about a book a majority of my staunchly Catholic family read, Heaven is Real. We discussed the book and how we were brought up with religion. We even got as deep as to discuss our beliefs in a higher being. This is usually a risky subject for discussion, but the conversation remained casual and flowed while we ate. I think it actually brewed a stronger connection between us.
When the check came, I insisted on paying. He was pulling out his credit card, but I forced the server to walk away with just mine. There was no way in hell I was letting the birthday boy pay. “It’s your birthday. I told you I wanted to take you out to lunch for your birthday!” I exclaimed. After saying, “That’s an expensive birthday lunch. You really don’t have to,” he thanked me.
When we finished, he decided he wanted to grab a coffee. Since I met him, he has become addicted to the Starbucks salted caramel latte, or as he likes to call it, “his salty pretzel drink,” which I find adorable! While we waited for our concoctions to be made, he took the opportunity to lean his back against my chest. For me, the little things matter a lot. Those signs of affection really speak volumes. We got our coffees and walked towards my office a bit before saying goodbye. He was out of his downtown comfort zone, so I relished guiding him around to find a subway back home.
We said goodbye with a gentle kiss. I put him on the subway and made my way back to the office. Of course, I had a smile from ear to ear as I walked. It was a short encounter, but I was happy to get to see him. It was his birthday lunch, but I think I got more out of it than he did.
Follow @onegayatatimeFriend Date
Posted by One Gay at a Time in Gay Dating on November 14, 2011
Before I met Smiles, I was chatting with a guy on OKCupid. After cruising the site, trying to find anything remotely resembling a prospective man, I managed to find a guy who was both attractive and seemed to have a great personality — at least based on his profile. He looked like he led an active lifestyle and was smiling in all of his pictures, so I sent him a message.
Surprisingly, he messaged me back shortly thereafter asking me to email him some pictures (my profile only has my torso pic). However, he added, “And just to be upfront about intentions, I’m seeing someone currently, but I’m so down to make legit guy friends. I don’t do well with the fem/gay scene so I’m always eager to meet more guys like us :)”
I wasn’t exactly thrilled, but I was also looking for friends. At the least, maybe I could get a wingman out of him. I responded, “Of course you’re seeing someone… All the good ones are!!! I can use friends just as much as I can use lovers ;)”
He seemed like a very genuine, down-to-earth guy. I was pleasantly surprised by his response. “Awww! Well you’re very cute. Why are you single?” he asked. We exchanged numbers and planned a time to meet on Thursday night immediately following work. Ironically enough, it was a night I double booked.
When my day was winding down, I texted him to confirm, but, he had to cancel. He had an impromptu second interview for a job, so I couldn’t exactly hold it against him for the last minute cancellation. Instead, I called up Sexy Eyes to see if he could grab coffee and already had plans later to meet Smiles for the first time.
I tried to reschedule with my new prospective friend, but I got no response after that. I wasn’t sure what happened exactly, but enough time passed that I lost interest. Then, out of the blue, I received a message, “Hey man, I broke up with my boyfriend 
So I’ve been in a funk. Sorry for flaking on you – I’m not usually like that, but the breakup wasn’t exactly amicable. If you want to give me a second chance, I’ve evened out and am down to chill.”
If you’ve ever read my blog, you know I’m all about second chances. However, now the roles were flipped. I was dating Smiles for a few weeks at this point, so this time I was the one looking for just friendship. For some odd reason, I didn’t make it a point to lay that out for him ahead of time, as he had done before the first time we planned to meet.
Wednesday after work, we met at Shima in the East Village, his neighborhood, for sushi. He was already waiting at the restaurant when I arrived. I sat and we immediately jumped into conversation. It was great because there was no tension or awkwardness. We jumped right in like we were old college buddies. I learned a lot about him over dinner — How he just moved to the city, what he wanted to do, what he did for fun, his family… The conversation flowed constantly. We really hit it off.
When dinner ended, we stood outside chatting a bit before he invited me back to his place to smoke and watch Archer, a show we found we shared a common love for.
The whole reason I went on this date was because my friends all encouraged me to date other people. They explained it was healthy to date a few people at the same time until you find one you really like. Things had become a but of a roller-coaster with Smiles emotionally. It went against every fiber of my being, but I decided to follow their advice. However, when push came to shove, I turned it into a friend date and couldn’t make a move. It was getting late, so after a full episode, I decided it was time for me to head home. I wanted to leave before things got awkward.
He may have thought we were on a date, but I was dating Smiles. And, as much as my friends told me I needed to be dating other people as well, I couldn’t do it. I couldn’t lead my new friend on while I had a strong interest in Smiles.
He walked me to the elevator to say goodbye. I could tell he was expecting a kiss. And, I can’t lie. I wanted to kiss him. I had a really good time, but like I said, I couldn’t lead him on like that. I knew where my true interests lay. I gave him a hug and said goodbye. I could see the disappointment in the expression on his face as he walked back into his apartment. I felt awful.
I knew I couldn’t leave things as they ended. I wanted a friendship from him, so I wanted him to know he didn’t just get rejected by me. I decided to text him to explain on my walk home.
I told him how great he is and how much I enjoyed myself with him, but I explained how I’d been dating Smiles since the night he first cancelled on me. He responded by noting, “Guess that was my loss.” We discussed it further. I realized I was wrong in not telling him my intentions going in to the date, but I didn’t know my intentions until the date was closing. I thought I could date more than one guy at a time, but it’s just not how I operate — At least not when I’d been seeing the guy for a few weeks. I could tell he wasn’t thrilled with the situation, but I had a feeling time would fix it, and we could start a great friendship.
Follow @onegayatatimeCentral Park Loop
Posted by One Gay at a Time in Gay Dating on November 11, 2011
After my amazing date with Smiles Saturday into Sunday, I was in heaven. Of course that only means I couldn’t wait to see him again! I had to keep cool. I couldn’t get all mushy on him already.
Before it arrived, I knew Monday would be hell for me. We had a pitch early Tuesday morning, so I would be working straight into the night on Monday to finish preparing. I was right. I barely had time to shoot him a text. Smiles also had a busy day, as a friend was in town with whom he needed to talk business. I typed, “Hey sexy man… Any chance I can interest you in dinner tomorrow or Wed night?” He responded, “Working out my schedule. [My friend] hasn’t told me what his is yet…” I told him to keep me posted. My schedule was fluid.
Following the pitch Tuesday morning, my team came back into the city and went out to lunch at Keen’s. I ate a whole lot more than I needed to.
After lunch, I went back to the office, and called it an early day. My boss told me to go home, but I had other ideas. I called Smiles to see if he’d be interested in a run in Central Park. We’d talked about running together once before, and I rather liked the idea. It worked out well when I called. I explained I was finished work for the day. He happened to be free and was up for the idea. We planned to meet at Columbus Circle in a half hour.
I ran up to the park from my office rather than taking the subway because I thought it might be quicker. I was already regretting such a big lunch. When he arrived, I walked up to him and gave him a light kiss. We walked into the park as we talked about the time passed since we last saw each other. I liked this conversation. He seemed to be opening up, and the relationship seemed to continue to grow.
Once we got to a running path, we picked up the pace. We chatted as we ran. I know it’s not the most romantic thing for two men to do together, but we both are very active. He runs triathlons regularly, and being a division I college swimmer, I try to stay in shape every chance I get.
I learned a lot about his plans with the visiting friend. I gave him some of my thoughts on his proposal, but he clearly knew what he was doing. He’s a very smart and entrepreneurial guy. I love that about him.
As we ran, the connection seemed to drop off. The conversation started to feel a bit forced. There were awkward pauses, and periods of silence, searching for something to talk about. Looking back, I feel like he was distracted. I don’t think he was fully present since he had so much on his mind.
We ran a good distance, but we clocked only an average pace. Neither of us had run in a few weeks. At one point, we needed to stop so he could take a phone call. That phone call turned into three because he had to take care of something from one of his projects. We were walking again while he talked. I didn’t feel it was rude, because he was working. It wasn’t even 5:00 yet. I had to respect that. But, it wasn’t what I had in mind when I called him to get out for a run.
When he finished his calls, we began to run again. As we neared where we entered the park, we cooled down by walking. Somehow we got on the topic of my size 14 feet. He was gibing me and poking fun at them. “There will be no drag for you! Not unless you are G.I. Jane.” I laughed. The thought of size 14 high heels was hilarious.
I suggested we go into the Time Warner Center so I could relieve myself. He agreed as we joked about the fat naked statues that adorn the lobby. He told me he wanted to take a picture of me molesting it. I declined, but we still joked about it for some time.
Smiles hadn’t had lunch, so after the bathroom, he was looking to grab a quick bite. We descended into Whole Foods and he whipped up a salad. We found a table so he could eat and I could sip on my iced tea to rehydrate. I was enjoying sitting there just watching him. He caught me a few times, and we exchanged flirtatious glances. Since he made fun of my feet, I found a gentle way to make fun of his hair, or lack thereof. He shaves his head, and he took my jokes with a smile. I didn’t have room to talk however, as my hair is receding as well. I’ve just done a good job of hiding it. We were having fun poking fun at each other.
He looked wiped out. He was supposed to be meeting his friend that evening for dinner. He got a text to come to his friend’s hotel for drinks before they went out. He was torn. He was entertaining the idea of going back into the park to take a nap. I told him he needed real rest before he went out, or he’d be no fun. I suggested he decline drinks at the hotel with his friend so he could take a nap and be more of a human being for the rest of the night. (By the way, I wasn’t worried at all about this friend. I’d seen pictures, and he certainly was not the type one hooks up with). Smiles agreed with me, and we made a move for the door.
When we got upstairs, we were heading in separate directions. I asked him for more details about his upcoming film screening in the Hamptons in conjunction with the film festival. I was heading out there for a wedding that same weekend, so I contemplated supporting him by attending the screening of a feature film he worked on. I was still feeling him out to see if he actually wanted me there, or if I was going to be in the way or a distraction. We exchanged a quick kiss, and I said goodbye.
The run hadn’t gone exactly as I planned, but it was still nice to get to spend time with him again. I always relish getting to see him and his smile. It never fails to brighten my day.
Follow @onegayatatimeRomantic Evening in the Park
Posted by One Gay at a Time in Gay Dating on November 10, 2011
As we left dinner Saturday afternoon following the opera, we began to walk north on Columbus Ave. I had no idea where we were going or what we were about to be doing, but I had a feeling I was going to enjoy the surprise. I was already enjoying the fact that he was being romantic enough to surprise me.
Finally we stopped at the corner of 67th to pop into 67 Wine. Call me stupid, but I was in the store for a solid two minutes before I realized what his plan was. I heard Smiles ask for a cold bottle of white wine, but it wasn’t until he asked for plastic cups that I realized his intentions. Apparently he wasn’t ready for our date to end. We were a few blocks from Central Park. He must have been planning a spontaneous picnic.
It’s been a looonnnggg time since a man put that much thought or care into a date with me. I was swooning from the attention. As we walked to the park, I had a smile from ear to ear.
We passed a family with a child being slightly rambunctious, and he stated, “Yea. The jury’s still out on that one.” I didn’t let that comment fall too far before I scooped it up. On our second date, he pointed out an apartment that would be perfect for two edgy gay men to live in, implying no children. I know children is the last thing one should be thinking about on a second date, but the comment caught me off guard. Children are definitely something I want in my life at some point. Hearing that he’s still entertaining the idea was reassuring. I said to him, “What? Kids?” When he acknowledged, I pointed out how he’d be a great dad.
We entered the park by Tavern on the Green. As we walked out onto Sheep’s Meadow, there was a plethora of people out enjoying a spectacular October Saturday. There were lots of frisbees and couples, much like Smiles and I, enjoying a nice evening in the park just as the sun was setting.
We found a plot of dry grass in the middle of the open field to sit and crack open our wine. He poured each of us a glass. I sprawled out a bit and leaned back onto my elbow to get closer to him to chat. It was really shaping up to be a very special day. A day a few hours earlier I wasn’t sure would come to fruition.
Somehow we got on the subject of high school hookups, which was very interesting to hear him talk about it. When he was in high school, he dated girls exclusively, as did I. I liked that about him for some odd reason. It made him a little “less gay,” if that makes any sense. He talked about his first time. At one point, after one of his stories, we even joked about Saran Wrap being used as a contraceptive. I talked about my upbringing and family. I learned my suspicions of his parents’ divorce were true. The conversation continued though college, finally ending in the real world post college. I found out when and where his love of cars came from (He owns a Mustang from the 60s I’m dying to take a ride in… Among the other things I want to do in it). I learned a great deal about him amongst those blades of grass. I caught a glimpse into how he became the man he is today.
As the sun went down, some cuddling ensued. It wasn’t until we couldn’t see very far in front of us that we decided to leave the park. After a short pit stop at the restrooms to relieve ourselves, we made a detour to investigate where some loud drumming and music was coming from. We discovered it was an impromptu drum session/dance party the broke out in the middle of the park. We stood and observed the celebration for some time, before out of nowhere, Smiles jumped into the mix and started dancing with one of the women. I loved his spontaneous spirit and was VERY impressed with his dancing skills. I was a little taken aback actually. I couldn’t stop smiling. I wasn’t sure if he expected me to join in, but I hadn’t had enough to drink yet to get my ass in that dance circle.
When we had our fill, we walked down a darker pathway. I took the opportunity to pull him aside for a quick kiss. I laid a big one on him. We continued on towards Columbus Circle without further plans. When we neared the subway, he pulled me towards him and said, “So I have a suggestion. Let’s go back to your place, put on gym shorts, and sit on the couch and watch a movie for the rest of the night.” My face lit up with a smile, and I said, “That sounds like a spectacular idea!” With that, we made our way to Port Authority to hop on the bus.
When we arrived at my apartment, I was surprised to find my roommates home with a large group of girls smoking on the balcony after a bar-be-que. I was less than thrilled. Our night of sitting on the couch alone was going to be heavily interrupted by a pack of young girls.
We poked our heads out on the balcony and said hi before heading to my room to put on more comfortable attire. Of course some kissing and heavy petting ensued while in my room, but we made our way back out to the balcony. Smiles planted himself in the middle of the group as if he’d known them forever. He joined their conversation and gave them advice while we all smoked. When Smiles and I had our fill, we went inside to order take-out to satiate our muchies. While waiting for the food, Smiles beckoned me to my bedroom. He was hungry for sex. After the day he showed me, who was I to deny him that pleasure. And, I too was hungry for sex.
However, if you’ve read my blog, you know I prefer to top. There was a polite standoff for a short period as to who was going to hold that position. No words were said, only body positions exchanged. Finally, I found myself in a weaker position and was conquered. If you’re keeping track now, that’s two points for him, none for me. I was okay with letting him top this time, but next time was definitely mine. This wasn’t something we discussed, and I wasn’t sure how to bring it up. I wanted to make sure he wasn’t exclusively a top, but I wasn’t ready to end it even if he was. It was a catch 22.
Warning: The following may be a little graphic for some. After some passionate time, he finished. He was continuing, waiting for me to finish. I explained to him I never finish from bottoming. I was insinuating that I normally top. I wanted to make sure he didn’t think I always liked being on my back. He understood what I was saying, but was a little shocked I never finish from bottoming. He was perplexed. This was twice now we were together where he finished, and I did not. This topic is worth a blog post on its own. Stay tuned…
We cleaned up and went back out to the kitchen just as the delivery man was buzzing. We took our food and plopped down on the couch to eat. As we settled in, the girls finally left the apartment. We decided to watch the second Transformers since Smiles had never seen it. I was happy just spending time cuddled up next to him. Being as it was a long day, I kept falling asleep on him — Literally on him. No matter how hard I struggled to stay awake, I continued to fall asleep. When the movie was ending, I awoke and felt really bad for sleeping on him.
We cleaned up our mess and made our way to the bedroom to settle in for the night. I had one of the best days I’d ever spent with another man. I slept with a smile from ear to ear that night.
When we woke in the morning, I made coffee. We sat on the couch a bit, chatting with my roommate about her night before we finally showered and made our way to brunch at Trinity along the waterfront. We sat outside, yet again enjoying the nice Indian Summer we were having. When we finished eating, I walked him to the PATH to head home. Standing in front of the PATH, I kissed him. I’d never kissed a man in broad daylight in Hoboken before — Especially not in one of the busiest intersections in all of Hoboken in front of everyone watching Sunday football at the bar across the street. I was expanding my comfort zone, and certainly for a worthwhile cause.
As I left him, I had an abundance of energy. The endorphins were flowing! I kicked myself for ever doubting his feelings towards me and put his birthday party out of my mind. With that, I all but floated home. Hopefully, things would only go up from here.
Follow @onegayatatimeAt the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 