Posts Tagged conversation
Never-Ending Date
Posted by One Gay at a Time in Gay Dating on May 29, 2012
I’d begun an amazing date with a spectacular man, and I couldn’t wait for what was to come next. Although I had been to Frankies 570 multiple times before with multiple dates, this time was special. I had an amazing guy to share a meal with. Ironically, my meal from days prior was so good, I ordered the same the again.
Conversation over dinner we great. It flowed like water downhill. We were both very flirtatious and chatty. On many of my other dates, there were long awkward pauses, but not on this one. Everything was just so easy. When I excuse myself to go to the bathroom, he leaned in requesting a kiss first. It was incredibly sweet and adorable. I really liked this guy. He was everything I was looking for.
I was just taking extra care to make sure I didn’t get ahead of myself. I had a history of falling for guys who would hurt me or not be interested in pursuing anything further. While in the restroom, I looked in the mirror to keep myself centered. All I could do was smile at my reflection like a giddy schoolgirl.
When I returned to the table, the conversation picked back up where we left off. My hand was on his leg under the table. His body language was very positive.
Our meals came, and we shared them with each other. Both of us were very happy with our selections. When the meal ended, we agreed to order a dessert to share. We got the crème-brulee. I dug my spoon into it and fed him a spoonful. It felt incredibly romantic. He smiled as his mouth closed around the spoon. We finished dessert and began to chat about what to do next. He was dancing around what I can only assume were his true motives. He said, “We can go have more drinks.” I interjected, “I don’t want to drink anymore.” “We can drop our bags at my place and go out. We could grab Pinkberry…” he added. I cut him off at the pass saying, “You can stop dancing around it. We can go back to your place.” He immediately smiled and agreed that was the best idea.
I wasn’t thinking we were going back to his place for sex. I knew there would be making out and a lot of heavy petting, but I wasn’t planning to give it up that easily. We hopped in a cab back to his apartment. He asked if I wanted to go to the roof, and I told him I would default to him. We were on his home turf. He could run the show. I picked the bar and restaurant. It was his turn to drive. Before we got to his place, he warned me of the condition of it. He informed me he lived like a frat boy.
When we got to his place, we stopped in his apartment on our way to the roof. I didn’t think he was as bad as he let on. We began making out on the bed. This, of course, led to many other things. Slowly but surely, clothes started landing on the floor in scattered piles. Eventually, we fond ourselves naked and engaging in a myriad of sexual acts, but penetration would never occur.
He was a very passionate man. I have found it nearly impossible to find a man whose intellect, wit and sense of adventure outside the bedroom matched their passion in the bedroom. He was a diamond in the rough. I wasn’t going to let this one go without a fight.
I noticed he was very into music. It was like he needed a soundtrack. I liked it. Every minute I was learning something new about him, and it was all making me like him even more.
We never made it to the roof. We ended up passing out on top of each other’s naked body. In the middle of the night, we both woke up. It was around 2:00. He offered for me to stay. I was under the impression that was already happening. I assumed I would just stay the night. We cuddled some more, and he turned out the lights.
When we woke in the morning, things weren’t awkward at all. I felt very comfortable with him. We talked about how we didn’t have sex and how that made us both happy. We didn’t need to rush things. I mean, I was spending the night on a first date, but I was happy true sex didn’t occur. I was also thrilled he was the type of guy who would just bring that up and not keep it inside for fear of saying the wrong thing. He spoke his mind. I needed to get back to that. Being with him might help me get back to that.
He was amazing. There was no question about it. We were both starving and decided to get dressed to hunt for some breakfast. We stopped by a few places before finally settling on Jimmy’s American Grill and Bar. We grabbed a table outside and picked up the conversation where we left off the previous night.
I let my freak flag fly. I felt so free with him. I told him all about me and my idiosyncrasies. I explained my Christmas Bash and all the work I put into it. He referred to me as Martha Stewart, and I expressed my hatred for that referral. I didn’t like that my cooking and entertaining had a feminine connotation. I told him I was more the Nate Berkus type. He laughed and agreed it was a better reference. I told him about my crazy coworkers and how we would make an amazing reality show. I told him about growing up on a farm. Everything I could think of, I brought out. He loved it all! I learned about where he grew up and his career in advertising. Every word made me like him more and more. He also told me about his friends. They texted him while we were eating to ask him to come to brunch 2.0.
Somehow, we got on the topic of The Hunger Games. I was reading the books, and he had already seen the movie. I told him I was looking forward to seeing the movie. He told me he would go see it again and asked if we could go see it Sunday. You could have knocked me over with a feather. He was already planning date number two before date number one concluded. I was thrilled and immediately accepted.
He walked me to the PATH to say goodbye before heading downtown to meet his friends at Elmo. We kissed each other goodbye and gave a long lasting hug. There was a homeless man panhandling next to us who said, “Get a room,” through a smile. He began laughing, and I started to crack up since I was the one facing him. I said to my amazing date, “That made my day.” Immediately, he replied, “You made my day.” I was in heaven. I said goodbye and went down the stairs to the train.
Later, I learned from checking his Twitter that when he checked in at dinner on Foursquare, he wrote, “Easy conversation + tasty food + hot boy = great date on a Fri night (@ Frankies 570 w/ 2 others)” and the next day at brunch, “When last night’s date becomes this afternoon’s brunch date (@ Jimmy’s American Grill & Bar). He really did like me. I was just finding it hard to take. It was like a dream. I couldn’t really believe it. I didn’t want to get too excited because I didn’t want to get hurt. But, honestly, who gives a f*ck. I was happy, and that was all I cared about.
The One I’ve Been Waiting For
Posted by One Gay at a Time in Gay Dating on May 25, 2012
Today is another Fast Forward Friday!!!
Hope you are enjoying these. It will help bring the blog a little closer to real-time. If you’re keeping up with the stories chronologically, please skip down to this morning’s post first, then read this one. I think it’s a good one! Enjoy!
Never before have I prefaced an entry by giving away some of the details of what’s to follow, however, I’ve received numerous comments from readers tired of reading my “sex journal.”
“Your blog used to be interesting when it was about your relationship with your ex bfs, but it turned me off when it became a sex journal,” wrote one reader.
We’re both on the same page here. I dislike writing about these trysts as much as you dislike reading about them. It’s bad enough I’ve lived them once, let alone having to live them all over again when I write them.
So, without further ado, I am pleased to present you a love story…
On a Wednesday morning in April, while on my way to work, I happened to poke around on Grindr a bit. There was a message from an interesting guy on there. We began to chat a bit while I walked. He seemed pretty cool. I was about to head underground, so I quickly asked him for his phone number so we could continue the conversation on the other side.
We chatted a bit over text, and I came to learn a few things about him. I explained to him I wasn’t looking for sex, so if this was his motive, he should move on now. I was there purely for dates and friends. He seemed okay with that sentiment, and the conversation continued for a bit. I tried to check his spontaneity and asked if he would be interested in drinks that evening. He couldn’t because he had to work late. That’s when I learned he worked in advertising. I explained to him, if anyone understood working late for a pitch, it was I. I explained I too worked in advertising. When he told me he worked downtown, I started guessing what agency. Ironically enough, he worked for my previous agency. He worked closely with one of my favorite ex-coworkers. We were really hitting it off and I was excited to meet him. We agreed to make plans in the near future.
Wednesday evening, I was on my way home from a mediocre date. I fired up Grindr on the bus ride home and noticed he was on. I messaged him to say hi. He and asked what I was up to. When I told him I was on my way home from work, he responded, “You’re kidding me! Let’s f*ck.” My heart sank immediately. I had such high hopes for him. I was crushed. “You don’t know who you’re talking to do you? This is [O.G.A.A.T.],” I shot back. He admitted to confusing me with someone else and began damage control. I think he immediately realized he lost any shot of anything with me, however, he still took the time to apologize profusely.
If you know me at all, you know I give second chances out fairly often. I decided to lay on the guilt a little bit, but also give him the opportunity to redeem himself. As I got off the bus, I picked up the phone and called him. His timing caught me at a vulnerable moment. I was turning my dating life around. I told him what he did wasn’t cool. Again he apologized. I told him I would turn a blind eye this once for one reason; a few days prior, I probably would have said the same thing on Grindr. I couldn’t hold it against him when I too had treated Grindr in this way. He fully comprehended what I was saying and promised not to let me down.
The following day, I asked him if he would be interested in drinks Friday for happy hour. He immediately agreed that would be a great idea. When Friday arrived, we made more definitive plans. Since I was done work before he was, I offered to come down to his neighborhood. I just told him to text me when I should start walking down there, and he did. I texted him when I got the bar, but he was still working. I told him I’d hang out by the bar for a bit. I walked a block to Starbucks, got a coffee and wrote a blog post. I needed a kick in the a$$, considering it was a Friday night after a long week. When nearly an hour passed, my patience was at its end. This guy was not winning me over by any means. I was a block away from the PATH and very tempted to just leave. Just as I was closing my laptop, I got a text from him. He was on his way.
We met on the street in front of Employees Only. He’d never been before, so I led us inside to order a round of drinks and find a wall to lean against. He apologized for taking so long and explained what was going through his head. He was working on something late and told the editor they’d need to pick it up again on Monday. He’d already used up one of his chances with me. If he messed this one up, there’d be no redemption. I thought it was cute, and I loved his honesty. We talked about our jobs and our shared favorite coworker. I told him about my coworkers and how we’d be excellent fodder for a reality show. (I really work with a circus of a crew, but I love them!)
We were really hitting it off. Everything just felt so easy. He was also incredibly easy on the eyes. I felt I was a bit out of my league here. He was five years my senior, gorgeous, smart, witty, well spoken, had a solid job, etc. Basically, he was the full package. I already knew he had a healthy libido as well, so we’d probably be fine there.
After two rounds of drinks, he took the opportunity to kiss me. I can’t tell you how much I loved that kiss. He was a real man, and he kissed me. I was crazy swooning. We decided to make moves. In our conversation, I was talking about what I do in my free time and mentioned the pier I lounge on directly across from the Christopher Street pier. He suggested we take a walk out there before grabbing a bite to eat somewhere.
We walked holding hands to the end of the pier. He took my bag, set it on the ground with his own, and we walked to the railing. He stood facing the water and pulled me in, wrapping my arms around him. It was incredibly romantic. While we talked, I nuzzled his neck. Things were so easy with him. There was no drama. There were no games. There was just us. I couldn’t believe an hour earlier I was ready to abandon our date and go home.
He turned around and hiked himself up so he was sitting on the railing dangling over the river. I was between his legs with my arms wrapped around him while we chatted. I decided to tell him how new to the game I was and tell him my coming out story. I figured I might as well get that out of the way, because if it was going to scare him off, I figured it was better sooner rather than later since I’d already grown so attached to him. He was totally cool about it. This is also when I learned our age difference of five years. Obviously I was fine with that considering Smiles was nine years my senior. He was cool with that as well.
As we walked to find dinner, he told me about his coming out story. It was interesting and not all that different from mine. I learned he was bisexual through college, which actually was reassuring to me. I liked men that had experience with women as well. It wasn’t a necessary skill I needed to see them utilize. I just liked knowing they’d experienced women as well and realized they were more attracted to men. It also generally proved to produce more masculine men, which I’m far more attracted to. I also learned in that conversation he was a cancer survivor. I didn’t know how this guy could get any better. He was like Superman.
The date was off to an amazing start. We were walking hand-in-hand to find dinner somewhere, and I didn’t want the date to end. I was on cloud nine. I think I floated the whole way. We finally arrived at a spot I was quite familiar with, Frankies 570. So familiar, in fact, I’d been there a few days prior. The date was just beginning. I couldn’t wait for the next course…
Follow @onegayatatimeThings Are Starting to Look Up
Posted by One Gay at a Time in Gay Dating on May 24, 2012
Wednesday afternoon, I went from having no dates to having two. I managed to schedule seeing two guys in the span of a few hours. I was being efficient at my “job.”
On my way home from a purely average date in Hell’s Kitchen, I once again checked Grindr for messages. The guy who I spoke to that morning happened to be on. We chatted a bit, but again, that’s another story for another day.
I already lined up a date with the guy I’ve been talking to for about a month. We texted a few times about meeting up but nothing ever materialized. I Facebook stalked him and found him very curious. He was VERY athletic, which I liked a lot, but we didn’t share a lot of the same athletic interests. He’s into skiing and cycling. I am not. It seemed we would get along, but I just wasn’t quite sure about him. The night could go either way.
He agreed to come over and share a bottle of wine. It was a little unconventional, but it was getting a bit late for a coffee shop, and this was a much easier solution. He was fully onboard.
He drove over and found parking rather quickly, which is a miracle in Hoboken. When he arrived, I buzzed him in and greeted him at the door with a hug. We went into the kitchen and sat at the counter to chat a bit. While we talked, I opened a bottle of wine, opened a box of wheat thins and cut up some cheese.
The conversation began with my neighbors. He used to live with one of the gay men my roommate and I spotted across the street in another apartment. I detailed for him how we watch them periodically since they’ve peaked our curiosity. I told him about the St. Patty’s party he missed and how we tried to get their attention.
Then we started talking about work. I learned he pretty much did exactly what Smiles did. It was that moment I noticed how he somewhat resembled Smiles in stature and look. He too had a shaved head. On top of that, there was the commonality of the excessive training and triathlons. It didn’t bother me because there were distinct differences, but it caught my attention. They were similar in job, lifestyle, legal problems, look, hobbies, etc. It was uncanny.
Through our conversation I immediately noticed his sense of humor. He seemed like a really great guy. I was consistently laughing with him about things, and we were hitting it off pretty swimmingly. I loved his sense of humor. We got each other pretty well.
When my roommate came home, he jumped right in with her, chatting her up while she navigated the kitchen. I found this very attractive. He could start a conversation with someone on the fly well. It was kind of a turn on.
We talked for hours, and I was really shocked how well we were hitting it off. He had to teach a spin class in the morning, and it was nearing midnight, so he told me he had to be going soon.
After a long awkward pause, we both went in for a kiss. I liked that I wasn’t kissing him. We were kissing each other. We both came to the same thought at the same time. We kissed passionately on my bar stools for some time before we stopped. He said, “We should have done that sooner.” I agreed through my smile. With that, we continued kissing each other. He was a decent kisser. I wished he was better because I was really enjoying his company. I just wished I could teach him to open his mouth more when he kissed. We kept kissing for a long time before it was finally time for him to go home. I kissed him goodbye and said goodnight. After he left, he gave me his phone number. Apparently, the number I’d been given was his “office” line through Google. I told him I had a really great time and apologized for keeping him past his curfew. He responded, “Me too. Looking forward to getting to know you.” I responded, “Likewise. Still smiling.” He told me he was as well, until his class in five hours. “Goodnight handsome,” he added.
In the morning, he was up early for spin class. I texted him when I woke to see if he made it through spin class. Not only that, he made it to yoga as well. We texted back and forth and discussed when we’d see each other again. We made tentative plans for the following week. Finally, I met someone who got my blood flowing — Someone who got me excited!
Follow @onegayatatimeAnother Boring Date
Posted by One Gay at a Time in Gay Dating on May 23, 2012
Tuesday night, I was happy to be home. My date with S.D. wasn’t bad, but it helped me realize he wasn’t the guy for me. We had too many differences of opinion.
I noticed on my calendar Broadway‘s birthday had arrived. I made sure to call him to wish him a happy birthday, but he didn’t answer. If I recalled correctly, he was in California for a vacation. I left him a message and told him to call me when he had a free second. I didn’t hear back from him for over a week. I was a little disappointed, however, we still maintain a friendship. His friendship is important to me.
On my walk to work Wednesday morning, I checked my Grindr messages. I began to chat with one guy, but that’s another story for another day…
I had a date planned that Wednesday with a guy I chatted with on OKCupid, but he ended up bailing on me at the last-minute. This time, I had no one waiting in the wings. I debated just lying low and going home after work, but another part of me didn’t want to waste a free night. I thought I’d reach out to my current roster to see if any of the guys were free to meet. I figured I might as well get a first date out of the way while I had the time. I was really looking at dating like a job. This was bad policy, but with someone like me who has a busy schedule, you gotta do what you gotta do. I sent out feelers to the guys to see who was available to grab a drink after work.
Ironically, two of the guys responded. One was in Hell’s Kitchen and the other lived in Jersey City. I wondered if I could schedule them both in the same night. Hell’s Kitchen would work out because I could just take the bus home, and Jersey City could work if he came to Hoboken to grab a coffee or a drink when I got home later. I wasn’t all that psyched about the guy from Hell’s Kitchen, so I assumed it would be a short date and work out.
The first guy picked a nice restaurant, Pier 9, at the north end of Hell’s Kitchen to grab a drink and maybe an appetizer. It just so happened to be right across the street from his apartment. We met just inside the restaurant. I wasn’t excited by what I saw. He wasn’t unattractive, but he wasn’t attractive either. That being said, I wasn’t writing him off based on looks.
He was a regular here. He knew a lot of the wait staff, and they took good care of him. We grabbed a seat and began to chat.
The conversation was pretty relaxed. We both decided to order wine, and since it was happy hour, we split a bottle at half price. We also noticed a great edamame appetizer on the table next to us and ordered that to split while we got to know each other. It was a very nice place, and the wait staff was super sweet to us. They could tell we were on a date and treated us as such.
We talked about our jobs, our families, life in the city, etc. It was nice conversation. Nothing was forced or awkward, but there was no spark either. He seemed like a really nice guy, and we agreed on a lot of things. I could see us getting along really well, but more in a friendship capacity than a dating one. I could see him being a good date for Sunday morning brunch to talk about the weekend and talk about guys.
We were there for a decent chunk of time. The date lasted about an hour all said and done. We finished the bottle and the appetizer and decided it was time to head out. I could tell he didn’t find a strong connection there either. I had to initiate the goodbye hug, and there certainly was no feeling behind it. This would make things easier. We left with the same expectations of not hearing from the other much after we parted ways.
As I walked to the bus, I started texting the guy from Jersey City. We’d talked more than a few times before. We’d become Facebook friends, and I was supposed to see him on Hoboken St. Patty’s when he was attending the gay party across the street from my apartment, but he never made it. I asked him to an unconventional date. I lined it up for him to come to my place and just relax with a glass of wine. He agreed that sounded like a great idea, so he came over shortly after I came home. We were finally making time to meet up in person…
Follow @onegayatatimeIs This Really Working?
Posted by One Gay at a Time in Gay Dating on May 22, 2012
Since my last date with Southern Drawl, he had been bothering me for another date. I was trying to take things slow with him. I wasn’t gaga for him by any means. He was growing on me a little, but he still left a lot to be desired.
We made plans to make plans after work Tuesday evening. I left work when he was about finished after trying to bang out a blog entry and made my way downtown to his office. I waited for him on the street corner to finish work for about ten minutes when it began to drizzle. I had not expected rain at all and had no umbrella. I was growing impatient. I called him, but he didn’t answer. Finally, I noticed him walking up to me at a very slow pace with his headphones attached to his phone.
Normally, I would greet someone I’d gone on this many dates with a kiss, but not him. He was too self-conscious. He was not out and was not comfortable with public displays of affection. This bothered me. I needed someone who could love himself enough to not care about everyone else.
We decided to walk downtown on the High Line. I climbed the stairs, and he walked behind me. We took a nice stroll south to find a place to grab dinner. We didn’t have a place in mind, but we had a neighborhood — the West Village. We talked about our days while we walked. Once again, he made a crack, and I didn’t respond well. It was always hard to gauge his sense of humor. We never seemed to be on the same page. If I joked back, he would tell me I was getting defensive and loud. It was insulting. He obviously didn’t get my sarcastic sense of humor.
When we reached the end of the High Line, we descended the stairwell and walked to find food. We passed more than a few places that looked good, but they didn’t have any available tables. They were either too crowded or they appeared non-desirable. We finally came to Frankies 570. I had been there, and the food is amazing. I hesitated going there for a solid second because I already had memories with Smiles there. We shared a really nice meal there one night after work. Then I thought about it, and it made more sense for me to expunge those memories. I could overwrite them with new ones. I didn’t exactly have positive associations with him. I felt used by him as a meal companion.
I suggested it to S.D., and we perused menu before going in. He agreed on the spot and was seated by the front widow at a nice table for two. We ordered drinks and chatted casually. It was nice to sit and relax and just talk about things and my day. We discussed his coming trip home. He was very excited. This would be the last time I saw him before he left. He told me he’d be sending me a lot of pictures from home and would call periodically.
Throughout dinner, he was much more demur than usual. There were no overtly sexual comments and no innuendoes. It was kinda nice. He asked a lot of questions as well. Usually, he was just talking away. It was nice to talk about our upbringings and his home, however, his sense of entitlement was still shining through. He spoke about politics and slavery. He told me stories of his family and how they basically still had slaves. He certainly wasn’t winning me over. I was never all that thrilled with the South’s way of doing things, and he was certainly perpetuating the stereotype in my mind. I also learned how important money is to him, and it was a real turnoff.
Slowly but surely, I was realizing this guy really wasn’t right for me. We had so little in common. I was simply enamored by someone paying attention to me and being interested in me. We were in a downward spiral.
On the positive side, my meal was spectacular. I ordered the rabbit ragu and enjoyed every bite. My drinks was pretty amazing as well.
When we finished eating, we sat there talking a bit more before heading out. When we finished our drinks, he accidentally spilled his water all over me. It was a bit humorous because we were just joking about it, and it embarrassed him immensely. The table next to us took notice of the large commotion this caused, as did the wait staff. We paid our tab and made our way out into the street.
He walked me to the corner to say goodbye. I could tell he was very uncomfortable. I was a block from the PATH and ready to head home. I was not going to a second location, and I was not going home with him. I think he was itching to hang out more, but I wasn’t interested. Just as I was about to go in for a kiss, he turned his head. I was partially p*ssed and partially happy. This was creating an out for me. I scoffed at him and began to walk across the street to go home. He chased me and stopped me on the other side of the street. I told him what he did was not cool at all. As he went in for a kiss, I played along, and at the last second, I too turned my head. Just then, a man was crossing the street and witnessed this. He began to chuckle to himself, and I pointed this out to S.D. He was embarrassed. It served him right. If he thought he had a chance with me, he’d have to sack up. I wasn’t about to date a closet case. I’d moved past that.
We said our goodbyes, and we finally did share a kiss. There was nothing magical. He was still self-conscious. He may have made a good friend, but I couldn’t see myself with him in a relationship. I finally came to see the light. I said goodnight and hailed him a cab. I put him in the cab and said goodbye. I wouldn’t see him for over a week. This would give time for things to settle and fizzle out. I wasn’t going to end things over the phone across state lines, but I wasn’t going to make myself available while he was gone.
After all, I was back out there searching for a real prospect. I needed a real man who could make me happy. I didn’t need to settle on a guy like this. I live in NYC. I fired up Grindr to check my messages on my walk home. There are great gay men everywhere. Now, they just needed to find me…
Follow @onegayatatimeRejected!
Posted by One Gay at a Time in Gay Dating on May 21, 2012
Monday morning I woke up. Since I wasn’t wasting so much time messaging guys on Grindr, I felt so much freer. I had no idea how much time I spent searching and complimenting guys on their torsos in hopes they’d see something they’d like and allow me to ask them out on a date.
I was also thrilled since I got to sleep in my own bed the night before. My parents came to visit for Easter weekend, and I gave them my bed. Sunday night, they offered to get themselves a hotel room so I could get a decent night’s sleep for work Monday. After I dropped them at their hotel with my sister, I came home and passed out. I love my parents, but I was happy to have my place back again. I’d spent the weekend playing tour guide. It was exhausting.
Even though I wasn’t sending out messages on Grindr didn’t mean I wasn’t checking them. I fired it up to see if my prince charming would ask me out on a date. I found quite the opposite. I blocked a fair amount of guys before I found an interesting message. I spent the weekend being celibate. One of the guys on Grindr seemed pretty normal and chill. We began to chat a bit before he offered to blow me. Like that, I was back in it. I had done such a good job of staying away from the simple Grindr stranger hookups, but I was horny after a weekend of being good. I made an exception of course and accepted his offer to blow me. What harm was there? I could enjoy myself before work and have a great day. “Sure,” I said in reply.
I gave him my address, and he drove over to my place on his way to work. I quickly hopped in the shower. He buzzed, and I called him up to my apartment. I quickly dried off and got dressed. When he got to the door, I brought him right into my room. I was wearing gym shorts and a tank. We made our way to my bed, and I sat down. Just then, he looked at me and said, “Sorry bud. I’m just gonna go.” With that, he turned around, sped out my door and left without another word.
I felt so rejected. What was it about me that scared him off. He made it all the way to my bedroom before darting. Was I that repulsive? Why the sudden change of heart!? I felt so dejected! My self-esteem shot down to an all-time low. This had never happened to me, and I suppose it was karma for all my Grindr trysts. It was bound to happen at some pont. I thought about all the times I wanted to do what he did and didn’t. I’d always regretted not standing up and walking out, but suddenly I no longer regretted it. I would have put those guys in a tailspin like I was going through. I did have to respect him honesty however. It was a catch 22.
I was horny from the thought of getting off before work, so I quickly finished myself off and got ready for work. I was disgusted with myself for bending my new rule, especially since I didn’t get anything out of it. Served me right!
That night I had a date scheduled with a guy I’d been chatting with for over a year. We met through Grindr and tried to grab drinks before I met N, but when I started dating him, things fizzled out. We chatted periodically on AIM, but nothing ever materialized. I even contemplated making a career shift to event planning, which this guy did, but we were never able to get together to talk about it. We simply kept it to a digital relationship. When things with Smiles ended, I began to look back at the guys I’d been chatting with. I hit him up and asked him out.
We made plans to meet at Ariba Ariba after work for margaritas and a bite. During the day, I stalked him a bit on Facebook. I noticed he was a camera whore. He took so many pictures in so many gay bars. He was totally a part of the scene. He was a fixture. I worried this would be a roadblock, but I was still optimistic. Maybe I could learn to love it.
I arrived ahead of him and waited on the corner. When I saw him arriving, I noticed how attractive his smile was, followed by how short he was and how “fun” he dressed. He was very cute. We awkwardly said hi and made our way inside. He asked if I was hungry, and I told him I hadn’t eaten, so we agreed to grab dinner on top of drinks. We were seated at a tight table and settled in.
We mainly began talking about work. It was very awkward. Considering we’d chatted so often online, you think we’d have been able to jump right in — Not the case. There were so many awkward pauses. I was struggling to find topics to talk about with him. He wasn’t exactly spurring the conversation on.
We started to talk about TV and what we watch. I thought that would be a safe topic and would spur further conversation. That only led to learning we had very different entertainment tastes. He watched a lot of Bravo TV like Housewives of… and other shows of the same ilk. I was more into the mainstream network TV. I wanted to have more in common with him, and I could tell he did too based on comments, but it was a bit of a struggle. I asked so many more mundane questions followed by mundane answers.
We ate our meals while we talked, but it was far from a great dinner. It was pleasant. The food was good, but there was no flow to the date. I was ready for it to be over. I was a bit disappointed since I thought we’d get along swimmingly. We just didn’t have good chemistry.
When we finished, we paid the bill and made our way out. We began walking through Hell’s Kitchen south together. He lived that way, and I was headed to the bus. When we got to a shop along the way, Tagg, he needed to run in and grab something for a friend’s birthday. I went in with him since I had nowhere to be. We had some fun chatting about random things in the shop. He made his purchase, and we continued south. When we got to his intersection, we exchanged a kiss goodbye, and he made a comment about hanging out again sometime. I agreed, but in my mind it would be under a friendly premises.
We texted afterwards, but was pleasantries and formalities. We exchanged that we each had a nice time, but that would pretty much be the end of us.
Follow @onegayatatimeVintage Closet
Posted by One Gay at a Time in Gay Dating on May 18, 2012
Before my trip to Washington DC, I started chatting with a few guys on Grindr. It was bad timing for the trip to come right after “meeting” them, but it would have to do. On my way back home, I made plans with a few guys over text for dates to get to know them.
One of the guys I was talking to was a bit older. He seemed like a great guy, and he was very interested in me. Of all the guys I started talking to, he texted the most. He seemed sweet, caring and attentive. While away, he asked how the blossoms were. He genuinely took an interest in me. He was texting me like a high school girl. I wasn’t annoyed. I was flattered. We made plans to grab a drink Wednesday evening after work.
Since Southern Drawl didn’t want to go to The Breslin, I proposed he and I meet there for a drink. It wasn’t far from my office, and it was pretty centrally located in Manhattan. We set a time, and I stayed at the office to kill time until he could make it there.
He ended up arriving early, and he texted me to let me know. I quickly left my office and speed-walked the ten blocks to the bar to meet him.
I wasn’t sure what I’d be meeting that night. From his picture, he looked like a very mature man. He had white hair, and he told me he was possibly getting a haircut before we met. I encouraged him to keep his longer hair since I liked it, but it was his hair. I didn’t know which hairstyle I’d be meeting.
I walked in to find him standing leaning against the wall. It wasn’t too difficult to pick him out of the crowd, however, he looked much older than I originally expected. I invited him to follow me to the bar and ordered us drinks. I managed to snag two bar stools just as someone was getting up to walk away.
We dove right into conversation about work. We both worked in advertising at one point, so we discussed that for a while. The more we talked, the more relaxed the conversation became. I didn’t see this conversation growing into a relationship, but he was a really nice guy. There was no reason why I couldn’t share a few rounds with a nice guy. I really didn’t think we were compatible.
Somehow we got into philosophical conversation talking about life in general. He really liked my outlook on life. I wasn’t putting on a show or anything. I was just being myself. He really responded well to this.
During our conversation, he came clean on his age and informed me he was 36. That’s how old Smiles was, so it wasn’t the issue for me. He did, however, look more like he was 42. I wasn’t sure if I believed him about his age. I wondered if he was lowballing it.
We started talking about family and his family house in the Hamptons. We got on the topic of coming out, and I told him how fresh I was to the gay world. He responded well to this and told me he was new himself. He came out to a few of his high school friends, and apparently it didn’t go well. For them, it became a problem of an identity crisis. They didn’t know who he was anymore. I told him how positive my experience was coming out and conveyed my sympathy about his experience. He also told me his family didn’t know either. It appeared I was more gay mature than he was. This was a first. This was a 36 year-old man who was still living in the closet. I didn’t think I could handle that. If he couldn’t accept himself by that age, the road was only going to get rockier as we went along.
After three rounds, the time came to go home. He expressed his desire to go on a second date, and I let on that this was a possibility. I didn’t want to lead him on and seem overly zealous about it, but I didn’t want to break his spirit. We walked to the corner and said goodbye with a hug. We exchanged a few texts after that, but obviously nothing ever materialized.
It wasn’t that late, so I decided to text M.E. and see if he wanted to come over. He did, and when he arrived at my apartment, we immediately went to the bedroom. Warning: The following may be too graphic for some. We stripped each other naked and got right down to things. There was a bit of foreplay and a lot of making out before I reached for the condoms and lube. Since being with him, I had unprotected sex with someone else. I needed to keep his safety in mind. While in DC, my results came back with no STDs and HIV negative, but I didn’t want to take any chances. We had amazing protected sex that night and fell asleep in a spooning position.
When we woke in the morning, we fooled around until we hopped in the shower. There, we had sex once again. I’m always horny in the morning, so this was even better than the night before. When we finished showering, we went back to the bed and had sex there. At one point, I even turned over and let him penetrate me. I felt I owed it to him. He was incredibly excited about it. This didn’t last long because, as he told me, he had a hard time keeping an erection after he’d been penetrated. I was okay with this, being as it’d been a long time since I bottomed.
We laid with each other, and I tried to finish myself off but to no avail. I had a dentist appointment to get to that morning, so I could no longer dawdle. I was already late the way it was. This was going to be a rough day. How was I ever going to concentrate on anything!?
M.E. gave me a ride to the dentist, and I gave him a kiss goodbye.
Follow @onegayatatimeSouthern Hospitality
Posted by One Gay at a Time in Gay Dating on May 17, 2012
After my lukewarm date with the doctor, I was ready to get back out there in search for a man.
I’m happy to report, which I’m sure some of you may have suspected otherwise, I was doing a great job of staying off Grindr. Granted, it was a short period of time, but I was thoroughly proud of myself. I felt like I’d joined GA. Every day not having meaningless sex was another day of Grindr sobriety.
Tuesday after work, I arranged another date with Southern Drawl. The last date was a bit crazy. Footsie under the table. Shenanigans in the bathroom. I was curious if he’d be able to behave this time or would he be looking for another quick trip to the bathroom.
We texted during the day to lock things down. I proposed The Breslin. I’d always loved their food, their drinks and their ambiance. He shot the idea down because he said the place was always full of hipsters. I had always been a fan of Sala 19 in the Flatiron District, so I proposed we go there for dinner. It worked out well because it was halfway between our offices. He agreed.
I had to wait at work for him to finish. When he did, I made my way south to meet him. I met him on the street corner, and we walked to the restaurant.
Dinner was very nice. He was well-behaved, and the conversation was good. I told him about my allergist appointment, and he told me about his day. We talked frankly about our last date. We discussed what went on. I learned he’d never done anything like that before. I was also learning about the guys he’d dated since living in New York City. When we originally spoke on the phone, I was under the impression he was new to the gay world. I thought he’d never really dated anyone before. Now, I was learning about all the guys he dated in NYC, as well as the guy he dated through college that he said I so strongly reminded him of and resembled. It was a bit unsettling.
In the middle of dinner, he told me he’d ended things with the guy he was seeing. He explained they’d only been seeing each other for two weeks, and things were never that strong. When I probed him to ask if he left the other guy because he met me or if he did it because he wasn’t satisfied with the previous guy, he told me it was the latter, but part of it was also due to meeting me. A big red flag went off in my head. Would he leave me for a better model?
I still wasn’t sure about him. I liked talking to him. I liked being with him. He was smart. He was nice. He wasn’t flamboyant, however, I wondered if maybe he was too “straight.” He was a bit homophobic. I’m not the most open about my sexuality. I’m not out to everyone at work. I don’t openly advertise my sexuality. However, if he wasn’t comfortable with himself, how could we be comfortable with each other. I couldn’t be sure about him. Was he right for me? I had no idea. Only more time could tell. I was keeping a distance as we moved forward. We had a connection, but was it strong enough to last? Was it what I wanted?
In our conversations, his southern entitlement shined through. It was an incredible turnoff. Where was the southern charm I’d seen so many times in movies. When I think of the ideal man, I think of Matthew McConaughey. He definitely has an ego and self-confidence, but he also exudes charm and sexuality. His confidence is not in your face, and he seems down-to-earth. Southern Drawl fit the other Hollywood archetype — The Southern plantation owner. He had an air or superiority that was hard to swallow. Many times, he laughed off these comments, making them seem like a joke, but I wondered if there was really something deep down that was more genuine. I wasn’t ready to date a snob. That $hit wouldn’t fly with me. I wasn’t going to let him get away with it, and I’d already started calling him on it.
When we finished eating, we split the bill and walked north to the PATH station. I said goodbye to him ont he street with barely a hug. He was uncomfortable exchanging a kiss with me in front of a city of strangers. I wasn’t thrilled by that.
On my ride home, I questioned why I was continuing to see Southern Drawl. He was definitely interested in me, and I was still intrigued by him. I wasn’t ready to write him off just yet, but I didn’t see a lot of promise or potential. I would continue to see other men and continue to see him until I was ready to make a definitive decision.
Follow @onegayatatimeHouse Call with the Good Doctor
Posted by One Gay at a Time in Gay Dating on May 16, 2012
In a strike of luck, in terms of my desire to turn my dating/sex life around, the timing of a family trip could not have been better planned. My parents, my sister and I were heading to Virginia to visit my aunt, uncle and cousins. The purpose of the trip was to see the cherry blossoms in Washington DC.
It was a fun trip. I got to see my cousins’ girlfriends and their children, many of which for the first time. Even though the cherry blossoms had already fallen due to an early bloom, it was still nice to get away and relax.
While driving back to New Jersey with my sister, I began attempting to line up dates with all the guys I’d been talking to before I left. As far as going on dates, the trip came at a bad time because it put a roadblock in the momentum. I kept up with the texts from the southern boy I’d gone on one date with so far. We were trying to line up a second date, as well as a few first dates with some other men I’d chatted with.
I got back to town on a Monday afternoon and tried to dive right into the dating. One of the guys I’d been chatting with was a doctor I met on Grindr. We exchanged pictures. He was very good-looking, very well-spoken and very charming. His response to my picture was, “Matthew McConaughey party of one?!” I was incredibly flattered, and suggested he consult with an optometrist friend. Although he had some promise, I wasn’t all that excited to meet him. I was going in with an open mind, but the fact that he was a doctor was somewhat of a turnoff. He would have no time for me, and I have come to realize I need someone who will be around and spend time with me.
We texted back and forth to nail down plans. As the workday was ending, I asked him what he wanted to do. He responded, telling me, “I honestly feel like I need a quiet night in. A bit drained here but would definitely like to have you over for drinks and conversation if you are up for that?” It was a bit unconventional, but I told him I was game. He gave me his address, and we set a time at 9:00pm.
I made my way into the city, bottle of red wine in hand, and walked to his apartment. I called Boston, and he shocked me by picking up. I wanted to hear how his birthday went and catch up. He further shocked me with a story involving an on-duty officer and himself that made me so proud. It was nice to hear Boston letting loose.
As I walked up to his apartment, I hung up with Boston. He lived in a very nice building. He answered the door, and we exchanged hugs. He had a gorgeous place. I came in and made myself comfortable on the couch while he opened the bottle. I felt quite overdressed when I noticed him in sweatpants and a t-shirt. I was jealous. I removed my shoes and sat Indian-style on the couch.
He was far more attractive than his pictures. His tight t-shirt showed off his chiseled body, and his face and smile looked very similar to Taye Diggs. I was slightly mesmerized.
It wasn’t long after we began talking that he let his guard down. The flamboyance came bubbling up, and it was really turning me off. I immediately lost my attraction for him. I could see us being friends, but I could never date someone like that.
We sat on opposite ends the couch talking the whole time. I learned about his job and what he does in his free time (which wasn’t much since he didn’t have much of it). He told me his specialty, and that dominated a majority of the conversation from then on out. Ironically, his specialty was relevant to me, and we got on the topic of safe sex and HIV for over and hour. It was incredibly educational on two levels. I learned a few things about HIV transmission and the disease itself, and I learned how little I know about the stuff I was so cavalier about days prior. I thoroughly enjoyed our talk, but I wasn’t attracted to him as a potential man to date. I would, however, love to keep him around as a friend.
It was late, and I needed to go home. He needed to go to bed. He walked me to the door, and I said goodbye with a kiss. He pulled back and made a comment on how he wished he’d only done that sooner. He really liked it and came back in for more. He was a good kisser too. I walked to the PATH and then walked home, and it took me a while to get there.
The next morning I noticed a text from the doc. “Off to sleep here, but just wanted to say thanks for an awesome date! I really had a great time meeting you.” I apologized for my lack of response and told him I was at the allergist to getting poked with various things to find my allergies. We exchanged small talk on the subject, and the conversation fizzled out. That was the last I’ve heard from the good doctor…
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, come to terms with it and admit it to myself, but it's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
Superman Returns
Posted by One Gay at a Time in Gay Dating on May 30, 2012
Sunday, I made plans with my Superman — My Clark Kent. I was very excited and could hardly wait.
I texted him and invited him to come over to Hoboken. We would take the motorcycle out for a ride before the movie. I ran a lot of errands that morning in anticipation of his arrival later in the afternoon. As the day progressed, the weather looked like it would cooperate less and less. The sky was covered with clouds and the wind picked up significantly. It looked like it would rain any minute.
I texted CK and suggested we hold off on the ride, and I just come into the city to see the movie. It would make things less complicated, and it would give him something to look forward to in the future.
He agreed with the new plan. I met him at his apartment with plenty of time to catch the movie. He suggested we hit up the rooftop since I didn’t get to see it the first time I was there. How could I say no to that? When I got to his apartment, we went directly up to the roof. We spent time checking out the sights, cuddling and taking pictures like we’ve been a couple for a year already. I was crushing hard!
We sat and talked, and he suggested we catch a later showing so we could relax and not have to rush to the theater. I wasn’t going to object to anything at this point. I was so happy. I was just going to go with the flow.
We finally made our way to the theater. He insisted on buying my ticket. I protested since there was no reason I couldn’t pay for myself, but he continued to insist. He wanted this to be his treat. I relented, but was sure to pick up the tab for the pretzel bites and soda.
We made our way into the theater and got great seats. Almost immediately, the PDA began between us. It wasn’t gag yourself PDA. We were simply holding hands or caressing each other’s arms. It was my kind of PDA. I was quite enjoying myself!
We held hands while we walked and at times put our arms around each other. I could hear a lot of people making comments, and some even began to shout or hoot and holler at us. A few of the comments were jeers and a few were shouts of support. This was not something I was used to, but it was something I would have to learn to shrug off. I’d walked through the city being affectionate with other guys before, but it never gathered this type of reaction. At one point, CK acknowledged the comments, asking, “Are they still honking at us?” I told him I thought so, and we kept walking. Frankly, I was a little surprised by it all. We were in midtown west — Smack dab between Chelsea and HK, two of the gayest neighborhoods in NYC. I had a feeling a lot of the commenters were out-of-towners, and many of them were young guys.
When we got away from the crowds, he commented how he liked how I was into the hand holding. “Not all guys are into it. I’m glad you like it,” he added. I told him I liked little signs of affection, but I wasn’t into the far more obvious public displays. I told him I’m not much for making out in public.
He also mentioned the idea that had we planned better, I could have brought clothes to wear to work the next day and spent the night, however, he was happy we weren’t taking things for granted. He was happy with the pace of things, even though he wouldn’t have been opposed to sharing his bed with me.
We laid on one of the outdoor couches together and got comfortable while we ate our ice cream. We talked for a while before we ended up making out. Things stepped up to the next level when he undid my belt and began orally pleasuring me with one eye on the door. It was risky but I wasn’t fully exposed. I liked his passion and excitement. I’d finally met my match in terms of a decent, normal guy with a healthy sexual appetite.
After some time, he asked, “You wanna continue this downstairs in my apartment?” I told him I was totally game, and we descended the stairs.
Warning: The following may be too graphic for some. It wasn’t long before we were both naked in his bed. There was significant foreplay before he asked if I wanted to penetrate him. I was completely engulfed in our passionate romp and nodded my head in definitive agreement. “Yes! Like no other!” I added.
Then, I’m not sure how things switched so quickly, but as I was grinding on his backside, and stopped to put on a condom, he turned to me and said, “Can I f*ck you?” A long time ago, I made a rule for myself I would not bottom for a guy unless we were in a relationship. It wasn’t something I really enjoyed, so only special guys would receive the privilege. I had very strong feelings for him. I wanted to share something special with him already. I could hear A’s voice in my head telling me no sex until the third date, but that voice in my head was no comparison to the passion of my other head. After all that thinking, I said, “Yes.”
Like that, he started making out with me, and he had me on my back. While we were making out, I set the open condom down on the bed. He was already putting it on. I thought he was going to top me after I topped him. I didn’t realize I was giving up my position first. I was a little disappointed, but I let it happen anyway.
This time was much easier. He slid in with no problem, and began gyrating. It’d been some time since my prostate was stimulated like that, so part of it was discomfort and part was unexplainable pleasure. I never finish from bottoming, but I always have a full-body experience. I rarely can walk afterwards — Not because I’m so sore but more so because my legs go limp.
He continued until he was close, pulled out, ripped off the condom and shot all over my chest. It was very hot to watch him explode with gratification. He expressed how great everything felt, and we both laid there incapacitated. He told me how awesome he thought it was that I would flip so readily and let him top me. I told him I thought it was the best way for any healthy relationship. Both partners get to experience it all. Even though I didn’t always enjoy bottoming, I found it to be the ideal situation.
We cuddled for hours after that. We even dozed off for a period. When I woke, it was two am. I checked the schedule for the next PATH and made sure I was on it at 2:30. I said goodbye to him with a very passionate kiss, and we talked about when we’d get to see each other next. It was clear I couldn’t get enough of him. Now, the question was, did he feel the same way about me?
Follow @onegayatatimeGay, Coming Out, Hooking Up, Sex, Homosexual, Gay dating, relationship, texting, Dating, Date, Penetration, gay sex, top, bottom, PDA, Friendship, love, New York City, grindr, kiss, Hoboken, New York, condom, Hell's Kitchen, movie, breakfast, holding hands, conversation, rain, HK, apartment, bed, position, Chelsea, cuddle, disappointed, weather, relax, passion, affectionate, ice cream, chest, hurt, errands, honk, theater, surprised, reaction, engulfed, rush, cuddling, on my back, stop, excitement, decent, spend the night, making out, penetrate, affection, backside, shrug off, doze off, caring, soda, pull-out, explode, foreplay, roof, shout, sights, slow, privilege, grinding, clothes, orally pleasuring, pace, shot, full-body experience, incapacitated, Superman, Pinkberry, Hunger Games, Clark Kent, motorcycle ride, clouds, less complicated, rooftop, taking pictures, later showing, buying my ticket, insist, pick up the tab, pretzel bites, great seats, gag, caressing each other's arms, street, discuss the film, encourage, comments, jeers, shouts of support, midtown west, gayest neighborhoods, young guys, out-of-towners, crowds, sharing his bed, shared spoonfuls, outdoor couch, undid my belt, fully exposed, normal guy, healthy sexual appetite, passionate romp, definitive agreement, rule, voice in my head, no sex until the third date, inside me, slide in, need a break, regain composure, delight, gyrating, prostate stimulation, discomfort, unexplainable pleasure, legs go limp, ripped condom off, gratification, healthy relationship, flip, passionate kiss
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