Posts Tagged dinner
Awkward Silence
Posted by One Gay at a Time in Gay Dating on December 8, 2011
Yet another video I’d like to share. This one is a music video for one of my new favorite groups, Duck Sauce. Great song and love the sexual connotations, but may not be safe for work depending on what you do. Enjoy!
On with the story…
Every Tuesday in Hoboken is free movie night if you have Cablevision’s triple play. I do not, but I have some very generous friends who do, and they lend me their card when they’re not using it.
I asked Smiles if he wanted to catch a movie and dinner. He told me he could possibly do dinner, but there was no way he could do the movie. He had to be up at 6:30 the following morning for a work meeting, so spending the night in my bed was off the table.
While I was finishing up work, he was moving his final boxes into his storage unit from Harlem. I agreed to help him when I arrived downtown, but when I got there, he was already finished.
I walked him back to his apartment. We talked about his day on the walk. I waited while he showered and changed after loading and unloading all those boxes to go to dinner.
While he was moving the boxes, both his parents called, separately. He was a little worried, so on the way to the restaurant, he dialed his mother. Smiles said he needed to walk a while, so we kinda just went for a stroll. We talked a little about work and how he got to where he is today. We stopped in a few stores on the way. We were walking for over a half hour before we settled on a spot to grab some grub.
We settled on Peels. When he returned to the table after washing his hands, the conversation was very dry. There were many long awkward pauses throughout the night. I struggled to think about anything we could to talk about. Nothing. I didn’t know what to do. We continued to eat in silence. It was incredibly awkward. I was so worried we’d hit that point already where we had nothing to talk about. I was petrified.
Was he distracted by the phone calls? Did something happen? Who knows?
When we finished eating, we paid the bill and began walking back toward his place and the PATH. We ran into a friend along the way, and Smiles chatted with him for a short while after barely introducing me. After we left the friend, he explained who he was and how close a friend he is. I was a little surprised. If he was such a good friend, then why was he so casual when introducing me. Maybe I didn’t mean as much to him as he did to me. Maybe I was putting too much of myself out there too soon. We’d been dating for a month and a half. I thought we’d be closer knit at this point, but maybe I was wrong. Maybe I had different expectations.
As we walked, he told me he was tired and a bit out of it. This wasn’t news to me after the awkward dinner we just had. He walked me to a crossroad and said goodbye. When I went in for a kiss, I barely received anything in return. It was almost like a child begrudgingly accepting a kiss from a grandparent. I felt like a piece of sh*t.
As I walked by myself to the PATH, I wondered if this thing had run its course. How much longer were we going to go before he fully opened up to me? — Before I didn’t have to wonder where I stood with him? I was tired of the uncertainty. It was dragging me down.
I needed to talk to someone, so I called Boston. No answer as usual. College always gets in the way of our friendship!
Next, I called LES to see what he was up to. No answer, so I left a message.
Then I texted the Principal just to say hi and see how he was doing. When I came above ground on the other side of the Hudson River, I received a response from him. We texted back-n-forth for the remainder of my walk home. When I got to my apartment, I immediately climbed into bed. I was depressed. This relationship was looking pretty bleak. Silence at dinner and an awkward kiss goodnight. Once again, maybe he just wasn’t into me.
The Principal and I continued to text over the next hour while I watched some TV. I explained to him I still had some feelings for him, however, the distance thing just wouldn’t work out for me. Apparently, I opened up a can of worms there. He really did miss me. I’m not sure why I felt the need to reach out to the Prinicpal that night. I thought I passed that chapter in the story. I think I did it for selfish reasons because I needed to feel wanted again. I knew the Principal would provide that for me. Looking back, I never should have done that.
In my mode of depression, I also responded to one of the guys who had hit me up on OKCupid. I asked him if he wanted to grab a drink sometime. I was taking my friends’ advice. I wasn’t going to put all my eggs in one basket. The guy responded, and we scheduled a date for the following night…
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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 @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 @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…
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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.
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