Posts Tagged awkward
Chauffeur
Posted by One Gay at a Time in Gay Dating on January 27, 2012
Waking up with the feeling of dread is never a good thing. Upon opening my eyes, I immediately knew something was wrong. It all came crashing back. I remember the conversation I had with Smiles the night before in my bed. It didn’t go as well as I would have liked it.
I needed to reassess the situation and make a decision before proceeding. One thing was for sure; I was going to proceed with caution. No longer was I going to invest so much of myself into a one-sided relationship. Smiles was still interested, and I had optimism the relationship could still progress towards something good. However, I could no longer devote so much of myself to someone who wasn’t doing the same for me.
I had that day off, but I had to wake very early. I needed to get my friend’s car keys before he went to work so I could take Smiles to the airport. When I volunteered to take the day off from work, I thought it would be a perfect way to see him off. I wanted to be both helpful and selfish. I wasn’t going to get to see him for a week, let alone on Christmas. The next best thing I could get was sending him off at the airport.
I climbed out of bed, put on clothes and rode my motorcycle over to my friend’s place. I swapped the bike for his car and drove back to my apartment. When I got back to my room, there were a few minutes left before Smiles was supposed to wake to get ready for his flight. I undressed and climbed back into bed.
Since we went to see the stage-show the night before, and he was working through the day before, he wasn’t able to pack yet. When my alarm went off, we woke and got ready to make our way into the city so he could pack.
I drove him through the Holland Tunnel and stopped in front of his apartment. There were no legal spots available, so I had to sit in the car while he got ready. When he got out of the car, Smiles checked out another street and texted me from his apartment: “If you wait another five minutes, you can park on the other street at the meters.” It was nice of him to check that out so I wouldn’t have to sit in the car alone the whole time.
I joined him upstairs and tried my best to assist. When he was ready, we got back into the car and set off for the airport.
My question from the night before was still in the back of my head. The car ride was rather quiet. It was as if we were both searching for something to talk about. I had yet another question burning a hole in the back of my mind. I had no New Year’s Eve plans, and all my friends did. I didn’t want to spend it alone, but Smiles hadn’t mentioned it to me. I had no idea what his plans were, but I wanted to spend it with him. The conversation from the night before didn’t change that. I was about to ask him if we could spend it together, but as we neared the airport, things got hectic because he wasn’t sure which terminal he was flying out of. That question would have to wait until later.
Once we had that settled, I found a space at curbside and helped him unload. We exchanged a very quick hug and kiss as he set off for home for the holidays. It was very unceremonious. I don’t know if he was self-conscious because we were in public or if it was because he still felt awkward, but I was very disappointed. That was not the way I wanted to be kissed by the man I was dating but not seeing on Christmas. That was not a proper goodbye.
As he walked away, he turned back and said, “I’ll call you later tonight.”
Since I had my friend’s car and the rest of the day off, I decided to run an errand I’d been neglecting. I took a route home that allowed me to stop by Michael’s to pick up a large panoramic photo I had framed. All that alone time is NOT good for me. It’s a sure to produce over-thinking and slight depression. I really didn’t know how to proceed. There was a fork in the road, and I wasn’t sure which road to take.
I decided to make a stronger effort to engulf myself with my friends. I wasn’t going to give so much of myself to Smiles, and in turn, I would fill that void with friendship. After I ran my errand, I went home and watched TV on the couch. I needed to distract myself with some form of entertainment, but it wasn’t working. I was still thinking about what I was going to do. I hopped on Facebook while watching TV and got a message from N: “I miss you buddy.” I hadn’t hung out with him since we broke up with the exception of my holiday party. Maybe it was time to give friendship with him another chance. I hit him up to see what he was up to. He was going out that night and told me he would keep me in the loop regarding his plans so we could hang out.
I know Smiles was settling in the with family, and I wouldn’t expect him to call. But, it would be nice if he called, even if just to let me know he landed safely. That night, I never heard from Smiles…
Follow @onegayatatimeHow to Get Out of My Own Head
Posted by One Gay at a Time in Gay Dating on January 23, 2012
Rules are meant to be broken. Apparently, in my mind this is true. I said I wasn’t going to reach out to Smiles after our awkward night and breakfast the following morning, but that didn’t last long.
Wednesday afternoon, I got an email including two free tickets to a screening of a movie in the city. It was Friday afternoon at 12:30. I had absolutely nothing going on at work as we were leading into the holidays. I shot Smiles a text Thursday afternoon asking him if he wanted to come with me after I left him.
He told me he wouldn’t be able to join me because he had to be on site for a project he was working on. I didn’t get my hopes up, so I wasn’t all that disappointed. I knew I wouldn’t be seeing much of him that weekend, so it was an effort to mend that but a failed attempt at that.
In the middle of the day, he called to see how my day was going. I was a pleasant surprise. He’d done this in the past, but it was out of the blue. He told me about his project moving forward and the progress he was making. I told him how useless my day was turning out to be. Maybe he did care about me. Maybe he just wasn’t good and showing emotions or talking about them. I still had some figuring out to do.
I finished my workday early. When I got home, I called my other friends who were attending the birthday party that night. I coordinated with them, and made my way to my D’s apartment.
During the taxi ride with D and his girlfriend, she asked me when she was going to get to meet Smiles. She missed him at the holiday party. I couldn’t think of a scenario in which she was going to meet him. I realized he never really hung out with me and my friends in general. I never really hung out with his. I was repeating my relationship with Broadway all over again. The only difference was, Smiles had a better schedule than Broadway. In the back of my head, I knew things between us weren’t perfect. I told her I had no idea when she’d meet him. I then explained to her why he was absent from my side.
I had fun at the party. I was running into a lot of people I hadn’t seen in a long time — Some even years. I sat and talked with one of my old college teammates, and he asked him the dating life was going for me. I told him all about Smiles, and he was very happy for me. In the back of my mind, all I could think about was, “Am I truly happy with how things are shaping up?”
Out of nowhere, Smiles called. He was between parties in a cab. I guess he had time to kill so he thought he’d call me. I stepped away from the party and walked out onto the promenade overlooking the city. I appreciated the call. It was nice to have him call out of nowhere twice in one day. It showed he really was thinking about me. I was a little bitter though. He was telling me about all these parties in detail, and all I was hearing was stories of parties I wasn’t invited to. I kept the conversation on the shorter side of things. It was cold outside, and I wanted to get back to my friends. If I wasn’t good enough to be by his side, he wasn’t good enough to steal me away from the party. We said goodbye for the night since I knew that’d be the last time hearing from him for the night.
On the way home that night, I discussed brunch with D and his girlfriend. They expressed their desire to do it in the city. I agreed and mentioned maybe inviting Smiles to join us. I knew he had things going on, but maybe he’d be able to meet us for a little while.
I texted him at 3:00am to see if he would be onboard for brunch. I told him I didn’t have all the details, but I would get them to him in the morning. He told me he would try to make it. He was making an effort. I was expecting to be immediately brushed off for other plans, but it was nice to see him entertaining the idea at the very least. Maybe things were improving.
In the morning, D and his girlfriend were too tired to head into the city. I told Smiles brunch was off. He told me he wouldn’t have been able to make it anyway. He had to work. We texted a little bit the rest of the morning. That morning, there was a fire on my block that day that engulfed an entire building. I sent Smiles picture messages, and he expressed concern for my well-being.
That night, we spoke on the phone. We talked about our day, and he told me about the party he attended. Again, I was a little bitter considering I wasn’t invited. I asked him if he was available for dinner Monday night since I wasn’t getting to see him at all over the weekend. He told me he’d have to get back to me. As the conversation was coming to a close, I asked him if we were going to exchange Christmas presents.
I’d actually been thinking about it since Thursday, but hadn’t remembered to ask him. I was a little afraid too. I didn’t know how to pose it. This is so unlike me. I should have just said what I wanted to say. I didn’t have the chance to ask him where we stood yet, so I didn’t feel comfortable asking him about exchanging Christmas presents.
The day before this conversation, I bought him two cashmere hats he’d expressed interest in. I bought them from one of my favorite online stores, Bonobos (They have really amazing stuff by the way. I highly recommend them, especially for proper fitting pants!). It would work out well because they offer free shipping both ways, so if we weren’t doing presents, I could return them.
So, I said to him, “Do you want to do Christmas presents?” He paused a second and responded, “Let’s not over-think things. I don’t think we’re there yet.”
And with that, we said goodbye.
Not there yet? Okay. Then where are we? How do you feel about me. We’d been together three months at this point. I didn’t see why we couldn’t exchange some nice Christmas presents. I wasn’t buying him a Rolex.
This just further motivated my desire to have the relationship conversation…
Follow @onegayatatimeMorning Paper
Posted by One Gay at a Time in Gay Dating on January 20, 2012
I woke up after a night of passion and disappointment with Smiles quite confused. I was trying to decide if my dream was reality or my imagination while feeling the disappointment of the truth of the situation.
I was suddenly aware once again how he shot me down when I wanted to discuss things with him the night before. He may have won that battle, but I wasn’t admitting defeat. It wouldn’t be long before we had that discussion. I was just waiting until the next comfortable moment to pop the question.
We woke up at a reasonable hour. Being the night after the office party, I wasn’t expected on time or to be particularly productive that morning. I had nothing planned for the day, so I took my time making my way to work.
I showered and prepped for work while Smiles checked his emails and got dressed. We decided to go downstairs from his apartment to a small diner for breakfast. Smiles grabbed the paper as we walked out the door, and we made out way downstairs.
We sat in a booth and had an interesting interaction with the hostess. It was obvious Smiles was a regular. He came there for breakfast about three times a week. She knew he didn’t need a menu, but handed me one so I could decide what I wanted for breakfast.
When the waitress approached, I witnessed yet another interesting interaction. The two of them went at each other with witty comments like an old married couple. We got our coffee and Smiles opened the paper. I know he had his morning routine, but was he really going to read the paper with me sitting there. Heaven forbid we actually talk to each other.
He perused one article about a woman who died in an elevator at a NYC ad agency. I was quite knowledgeable about the incident, so we discussed it a bit, and surprisingly he put the paper away. I think he realized how rude it was.
We got our food and the chatter was minimal. After we paid our check, I walked back upstairs to use his restrooms before heading uptown to work. I also brushed my teeth since I finally remember to bring a toothbrush. So many times I spent the night, and had no option for brushing my teeth other than a toothpaste covered finger. After I finished, I informed Smiles I would be leaving the toothbrush in his medicine cabinet. At this point, I didn’t ask. I was telling. He didn’t have a choice here. I know the toothbrush can become a symbol in a relationship for taking things to a new level, but I didn’t care. If he wanted to read into it, so be it. Didn’t matter to me — The toothbrush was staying.
He walked me to the door, and we have a very unceremonious goodbye. It was very awkward, and I wasn’t sure what the deal was.
As I walked to the PATH to head to work, I started to think about Smiles and I. Things had to change. I’d had enough of the run-around. I needed to know what we were. I didn’t need a label. I just needed to know how he felt about me. I was done putting so much of myself into something I was so unsure about. I couldn’t read him. We were going to have that discussion, and we were going to have it soon. I needed answers, because I wasn’t going to drive myself crazy trying to figure him out anymore.
Later that day, I invited him to come with me to a birthday party the following night, Friday. He informed me he was already triple booked for the night and wouldn’t be able to come along.
This was yet one more confirmation for me he wasn’t that into me. I had a party to go to, and I didn’t think twice about asking him to come with me. He already RSVPed for three parties and didn’t invite me to a single one. I also learned he had two parties on Saturday and one on Sunday. Yet more things in which he didn’t think to include me.
I resolved myself at that point to waiting him out. If he was interested in me, he was going to have to start chasing me a little bit. I wasn’t going to call. I wasn’t going to text. If he wanted to talk to me, he’d have to make the effort…
Follow @onegayatatime5th Annual Holiday Bash
Posted by One Gay at a Time in Gay Dating on January 12, 2012
The day of the party finally arrived. Something I start planning a year in advance was coming to fruition.
I was a little bummed however. A few of my best friends weren’t going to be able to make the party. D and his girlfriend were attending a wedding. J and his girlfriend couldn’t make it since she had finals and needed to study. A and her boyfriend were traveling out-of-state. There were still about 35 other people coming, but it wasn’t going to be the same without them. I was even more disappointed because many of them hadn’t met Smiles. I wanted to introduce him to my closest friends. Apparently my holiday parties have also developed a reputation as being my new “boyfriend” unveiling.
I was crazy all day preparing. In an act of desperation, I asked P to come over early and help with the final touches. She hauled ass and rescued me. My college teammate was also visiting from Maryland, and she pitched in to help finish things up. It would have been a mess without them.
When 7:30 rolled around, guests were supposed to be arriving. Instead, I was just hopping in the shower. (Next year I really need to hire someone to help me work the event.)
After I showered and dressed, I came out to the kitchen to find no one had arrived yet. Everyone’s late arrival was working to my advantage. People began to trickle in. Smiles was one of the earlier guests to arrive. He showed up with a bottle of wine and a very neatly decorated present. We exchanged a very nice kiss, and one of my old roommates shouted from across the room, “Oh. So that’s the new boyfriend!”
I cringed. He used the “B-word.” I should have looked at Smiles’ face to see his reaction.
I took Smiles into my bedroom to put his coat down and thanked him for the present. I unwrapped it, and it was a very cute tree ornament — Such a sweet gesture, especially for him! I gave him another big kiss to thank him.
More guests arrived, and the night was progressing pretty smoothly. Someone was commenting on Smiles helping me with some of the party maintenance and how he was so much “better than the last one,” referring to N. Just then, the door opened, and N arrived. The room got pretty quiet and everyone turned to me to see my reaction.
I walked over and gave him a hug. It was slightly awkward. Luckily, I was in the middle of things, so I didn’t have to linger on the awkwardness. When I finished, I walked over to him and pointed out all the food. He was overwhelmed by it all, and told me he was going to sample one of everything and let me know what he liked best.
I felt torn all night, and this happens every year. I feel like I never get to spend that much time with everyone because there are so many people there to talk to. There wasn’t even much work to be done during the party. I do a good job of planning ahead of time so that doesn’t happen.
My sister continued to give me dirty looks since N gravitated to her, being one of the few guests he knew.
I was having fun, and I was maintaining a good level of inebriation. Things were going well.
After a while, N was leaving to meet up with some friends. I was talking to Smiles at the time, so I introduced them, and they began to chat a bit. After he left, I told Smiles he was the ex. “Oh. He’s really nice.” I told him how he hasn’t made the effort to be a friend since things ended, and Smiles scolded me for being bitchy. I was being ever so slightly bitchy, but I thought it was humorous this was the stance he was taking. In reality, I didn’t want to be bitchy. I wanted my friend back…
As the night progressed, I received numerous praises for the food and the apartment. They couldn’t believe I whipped it into shape in the amount of time I had. Comments were also made looking forward to next years party and the food I prepare. I warned them an invite is no guarantee for the following year. It’s my way of making sure I maintain friends ;). Two comments were repeated a lot throughout the night I really appreciated. First, everyone told me how skinny I looked. That’s never a bad thing to hear. Secondly, they all told me how great Smiles is.
When things died down a bit, I took the opportunity to go out on the balcony with some friends and smoke a little. I think it put me over the edge a bit on top of all the alcohol I drank. I switched over to water to regain my composure.
We never did make it to the bar. Part of that was Smiles’ doing. I was game to move things to a local pub I frequent, especially after the continued insistence of my sister. However, Smiles was ready to call it a night. I’d already drank a lot, and it was getting late, so I gave into his desires. I said goodnight to the last guests as they left and got my teammate from Maryland settled for the night since she was staying over.
Smiles was a superstar for me that night. He took care of me and made sure I wasn’t getting too drunk. He helped clean up all night and remove trash. He schmoozed and chatted with my friends. I was very proud to be standing next to him at the end of the night. I was finally getting support from him the way I tried to support him. It felt really great.
That night, I fell asleep relatively quickly in his arms. It felt perfect. I was happy, and the only thing on my mind after that was sweet dreams…
Follow @onegayatatimePostponed Plans
Posted by One Gay at a Time in Gay Dating on December 6, 2011
On Thursday afternoon, I made plans with Smiles to go out with him Friday night. We planned to grab dinner and then go out the bars for a night on the town finally. However, that plan would have to be postponed.
Thursday night, he sent me a text explaining he forgot he had dinner plans in Brooklyn and then a birthday gathering in the West Village. He quasi invited me, but added, “That’s probably not exactly what you meant when you said night out on the town,” he added.
I suggested we simply postpone our plans one night. It was still relatively early in our relationship, so some space can sometimes help. I didn’t want him to get tired of me. I would use the time to go out with my friends since I was spending many of my weekends with Smiles or traveling.
Friday, I went out in Hoboken with my friends. He texted me to tell me he got a new phone. I was thrilled to know he was thinking of me even though I wasn’t with him (Or, at least that is what was going through my head as I read it).
Saturday morning, I woke and was feeling very productive. For quite some time, I wanted to trek down to the Financial District to check out the Occupy Wall Street movement in Zuccotti Park. I wanted to take the nice camera from work with me to snap some cool shots of the protestors. I didn’t want to do this alone. It was something Smiles and I discussed many times. I tried texting him and then eventually called him to see if he would join me. He was doing work, so he wouldn’t be able to join me until later in the day.
Since I knew he was by his phone now, I sent him a sexy picture of myself from the summer with the caption, “Wanted you to have a sexy picture for your new phone.” He responded, “Haha. Love it!”
I tried a few of my other friends to see if they’d tag along, including LES. After much convincing, I was able to get him to join me, but under one condition. I had to come by his place to smoke first. I agreed and also proposed we use up my Groupon that was expiring that day.
When I finally got to LES’s place, we smoked and got on our way downtown in a cab. The sun was setting quickly, so I proposed we just grab something quick for lunch instead of using the Groupon.
We got downtown to the Occupy movement, and we began exploring. I took many pictures and was even approached by an editor from The Suit Magazine asking me to send her some of my shots. She was looking for pictures to use in an article.
After we had our fill of protestors, we made our way to Wall Street. While walking, LES said to me, “So what’s the deal with this other guy? How old is he? What does he do?” I knew exactly what that question was. I interpreted it to mean, “What does this guy have that I don’t? What makes him so special.” It was an awkward moment, but it was bound to come up at some point. I really liked Smiles, but I also really enjoyed LES’s friendship. I didn’t want to create too many waves or hurt anyone’s feelings. When we got to Wall Street, we found they were filming Batman, and we wanted to check it out. By the time we got there, they were cleaning up the “set.”
As I was walking LES home, Smiles called. He finished work and was ready for dinner. I wanted to go home, shower, change and drop off the camera before we went out. I told him I would meet him for dinner later, and we made plans. I felt very guilty having that phone call with LES walking next to me.
After I cleaned up and changed, I met Smiles in Chelsea for dinner. We had no location picked out, and ended settling on Elmo for dinner. Conversation during dinner was great. He had a very productive work day, and I feel he let me in even more. He was opening up more and more every time I saw him. We were finally peeling back the layers of that onion.
After dinner, he proposed we go over to Barracuda. I’d never been and have always been leery of it. I’m not a fan of gay bars. They make me uncomfortable.
When we arrived, I learned he knew two of the bartenders. I had met them before as well. They were both very good-looking and pretty unforgettable. They were at Smiles’ birthday gathering. Barracuda wasn’t anything like what I expected. I was expecting a flashy club like seen, not a dive bar. I immediately felt more comfortable.
That is until a tall overly friendly black man came up behind me and started feeling up my chest with his arms around me. He was a feisty one, and I wasn’t interested. I made that pretty clear by my extremely uncomfortable facial expression. Smiles on the other hand was playing ball. I assumed it was a friend of his, until I learned he never met the guy before. This was just Smiles being his charming self.
Because I wasn’t completely comfortable, I drank a little more excessively than I should have. On top of that, Smiles’ ex arrived. I had no problem meeting him and talking to him, but I did have a problem when Smiles said to me, “I hope you don’t mind, but I’m going to steal away with [him] for a minute. I haven’t seen him in a while, and I need to chat about some things.” Based on the interaction, I wasn’t worried that he was going to do something with his ex. I was more annoyed I was being ignored in a place I’d never been before where I wasn’t completely comfortable and knew no one else.
I entertained myself by watching the bartenders cutting off the tall black man because he was being obnoxious to everyone at the bar. However, for me, the drinking continued — In excess! I drank so much, the bartender started giving me free drinks. I drank my face off. I was hurt and p*ssed. This little chat went on for a long time. There was some flirting and maybe Smiles wasn’t 100% over him, but I was okay with that. It’s natural. I wasn’t okay with being ignored! When the conversation ended, Smiles said to me, “How come you’re so quiet?” What the hell was I supposed to say to that? — “I’m quiet because you just ignored me for the past half hour?”
Next thing I know, when I woke up in his bed, the first thing I noticed was I was naked. I never sleep naked. The second thing I noticed was some lube on my backside. I couldn’t for the life of me remember anything about the night before. I don’t remember much after that. I don’t remember getting my coat from coat check. I don’t know how we got back to his apartment. I don’t remember climbing into bed.
I racked my brain to remember anything from the night before. The only thing I could conjure up was a flash of about ten seconds of sex with him on top of me. It was a very scary feeling! I’d blacked out before, but never have I blacked out sex. I was the only one ordering my drinks all night, but I couldn’t 100% rule out the possibility someone roofied one of my drinks.
I never mentioned to Smiles my panicky thoughts. There is no chance in hell Smiles would have done that to me, so I wasn’t worried in that respect. I knew he would never take advantage of me. I was probably pretty lucid in my drunken state, if previous history has anything to say. I was worried I may have done something to embarrass myself. I decided to play it cool and pay close attention to how the rest of the morning progressed…
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 @onegayatatimeBirthday Smiles
Posted by One Gay at a Time in Gay Dating on November 8, 2011
I’m not gonna lie. I was nervous. I don’t get nervous very often, but I wasn’t quite sure the situation I was walking into.
Smiles had his birthday at The Jimmy, a rooftop bar at the James Hotel in lower New York City. As nervous as I was, I set no expectations going in. I didn’t want to concoct all these crazy scenarios in my head, only to not see them play out.
The morning of his birthday party, I put A LOT of thought into what I was going to wear. I care about what I look like on a daily basis, but there was so much more going on here. I was nine years his junior, which meant many of his friends would also be a fair amount older than I am. I wanted to make sure I didn’t look like “who brought the child.” I tried on numerous permutations of clothing until I finally settled on one I felt comfortable with. I even consulted with my female roommate who works in the fashion industry. I wanted to look mature and smart, but I also didn’t want to look like I was trying too hard. (I’d like anyone to argue against me that I don’t over-think things too much).
I finished work that day at 5:00. Smiles and I had tentative plans to grab dinner before his party if I got out of work at a decent hour. When that time came, he was unable to keep those plans. He had a lot of things he still needed to do before the party, so he told me we would grab dinner with one or two others following the birthday gathering. I found something to snack on, and when the time came, I leisurely walked downtown to the hotel.
I had never been to there before. When I arrived I had no idea where I was going, which only heightened my anxiety. Finally I reached the rooftop bar and was able to find Smiles standing out on the deck by the pool. I walked up to him and was welcomed by an embrace, no kiss. Still early in our “relationship,” and not fully knowing the situation I was walking into, I didn’t initiate a kiss myself.
After a minute of small talk, I walked to the bar to grab an adult beverage for myself and a soda water for Smiles. I learned the night before he was not going to be able to participate in the libations due to the cleanse he was going through for his Ayawaska ceremony.
When I returned, he had a glass of champagne, which he felt obligated to sip since someone purchased it for him. I held on to his soda water for him until he needed it. He began introducing me to the friends he was speaking to at the time. He simply introduced me by my name, or a few times, “This is my friend,” and then my name. I had no expectations, but I was curious how I would be introduced. Certainly not boyfriend, but maybe as the guy he’s been seeing? No dice.
Early in the night, Smiles introduced me to one of his friends. This guy was younger than the majority of the crowd, and I made him buddy for the night. We hit it off and shared similar senses of humor. I knew Smiles would be preoccupied all night with his guests, so I prepared myself to be more social than I normally am. I didn’t want to be a wallflower or that creepy guy that lurks around and talks to no one. I was happy to have found someone to pal around with for the night.
Then the question I was dreading all night came up. My buddy asked me, “So how do you know [Smiles]?” I simply replied, “Recent friends.” We both smiled big, and he looked at me with a perplexed look. “That’s all I’m going to get?” he asked. I took a second, cocked my head to the side as I thought about it, and simply replied, “Yup.”
I then turned the question on him. Apparently they met on Fire Island and were just casual friends now. I wasn’t sure of the timing of this, but my instincts told me they hooked up at one point. To any normal guy, these things don’t pop in their head, but Smiles and I did meet on Grindr.
As more friends of the younger sect (all probably about five years older than me still) started showing up, my buddy and I began chatting with them. The question came up many more times asking how I knew Smiles. When others answered, there were a few “mutual friends,” but there was also a, “the old school way — Craigslist.” My brain was in motion. In my mind, my stock plummeted right then and there. Obviously he was still close with these guys if they were coming to his birthday party. Was he still seeing any of them. We were by no means exclusive. But, seeing these guys in person made me uncomfortable. However, I soldiered on.
It had been a while since I saw Smiles, so I circled back to him. He was starving. I offered to grab him something to eat just as he was simultaneously asking me to (keeping in mind his special dietary needs on top of the new ones for the cleanse). He pointed out “his” waitress for the night. He handed me his credit card, and I ordered him some tuna tartar tacos. When they arrived, he scarfed them down as to not miss a minute of his party. I was happy I was the one to which he turned to take care of him. He enjoyed them so much, he went back for seconds.
When I returned to my conversation circle, my buddy had departed. I was very disappointed because I wasn’t thrilled with anyone that was left. However, I continued to make small talk for the remainder of the night.
The time came to grab dinner. Smiles gathered a small group of about seven of us. We walked across the street to Cafe Noir and grabbed a table. Smiles sat at the head of the table, and I made sure I snagged the chair to his right.
The whole time at the restaurant, Smiles felt a little distant. I began to read far too much into that. I wondered if he was doing that because someone else would be offended if they saw him being affectionate towards me. Was there another “me” at the table? I was shocked I got an invite to his birthday gathering so early on. Who’s to say there wasn’t someone else in the exact same position?
I had my hand casually under the table and was rubbing his knee periodically. I wanted to see how he’d react. Nothing. I was a little hurt and confused.
I wanted to make a good impression on his friends in front of him. I was able to contribute greatly to the conversation over dinner. I attentively watch the news and stay up on current events, so I was actually the local authority on the topic of conversation. I wanted to prove to him I could hold my own.
When dinner ended, we walked outside in a large group. Many of his friends were going to smoke and invited him to join. He declined (the cleanse) and said he was going home. They also specifically asked me if I would come, but I too declined. I was hoping I was going home with Smiles. We split from the group and walked towards his place.
We weren’t a block away before he said, “Do you mind if I throw you in a cab instead of walking you up to the PATH since I don’t have a jacket and I’m freezing?” Apparently I would not be going home with him that night. I assumed he would invite me back to his place considering it was 1:30am. I even brought a spare shirt to work that morning for the following day should I be spending the night in the city. That wasn’t going to be the case.
At that point, I said goodbye to him on the street and began my trek up to the PATH. I was dreading my commute home since everything runs on a sparse schedule at that hour of the morning.
It also turned into a very long solemn walk because I was very disappointed with how the night played out. I felt so far away from him. A few nights prior, I thought I made so much excellent headway with him when I got an invite, but after the event, I had a very different picture in my head.
I tried not to let it get to me, but I can’t lie. It ate away at me for the rest of the night and into the next few days. I’m sure the fact that I had about six Johnnie Walkers didn’t help. At dinner the night before, he casually mentioned taking me to the opera that Saturday, so it was planned I’d see him again, and soon. But, it was mentioned so flippantly, I wasn’t sure I was officially invited. So many crazy ideas were floating through my head.
I was trying to follow friends’ advice to make myself a little less available to him. I was told I should make him seek me out, instead of the usual me seeking him out.
With that, I attempted to go about the rest of my week without driving myself insane, but that wasn’t going to be easy…
Follow @onegayatatimeBlackout Regret & Poor Life Choices
Posted by One Gay at a Time in Gay Dating on August 5, 2011
On Thursday, I talked to N on GChat during work hours. It was simple banter. At the same time, I was confiding in NC. We talked about the conversation we had, and he consoled me. He told me, “You’re a good looking guy, good job, etc. Don’t set yourself up to get hurt.” I said, “Thanks! I really needed that!” “It’s true,” he said. “It’s true. I woulda hooked up with you. Not that it means much.”
I had a feeling this was true. I could feel the sexual tension when he stayed the night in my roommates bed. I responded, “And yet, you didn’t. Haha.” “Had I had a few more drinks and wasn’t planning on moving in with you, I woulda suggested cuddling that night,” he replied. This was welcome information considering I felt the same way that night, so I let him know: “And had you not been planning to move in, I totally would have.” I further thanked him and explained, “I know I’m hot and I’m a catch, but for someone to do this to me, sapped a bit of my confidence…”
By the end of the day, N informed me he was going to a work function following work. Thursday was a typical night for me to meet up with friends at my favorite bar, but I wasn’t particularly in the mood to go out with them.
Instead, when I got home, I texted my new gay gym buddy and asked if he was going to be at the gym. He was, so I told him I’d meet him there. Over the past few weeks, I saw him periodically, and we chatted. I would keep him in the loop on my failing relationship, and he would chat with me about his issues. Together, we were providing a little bit of therapy for each other.
I got there and had a chat between lifting. I could tell he was starting to get better, but I certainly was headed downhill since he first met me. I didn’t want to drag him back down with me, so I only told him some of the highlights.
When I was nearly finished lifting, N texted me, “Hey. You wanna go out tonight?” Of course my heart lept a little. I was happy he wanted to spend time with me. Maybe this friendship thing wouldn’t be so hard. Maybe we could shift right into friendship mode with no speed bumps. I played it coy, however. I asked him what time and where. Then, I informed him I was still at the gym and had to go home, shower, eat, and then I would be ready. Since he was still at his work function, the timing would work out perfectly.
As I left the gym, I wondered if this was a group thing or just the two of us. We still had a few things we needed to chat about, and I wasn’t sure if tonight was going to be the time for that conversation. I had said to him, “Maybe sometime we can get drunk and put it all out there and have a good laugh about this.” But maybe this wasn’t that sometime.
After I showered I came out to the kitchen to find L there.. I filled her in on the latest details and began to pour myself some Johnnie Walker. I texted N and asked him what time he wanted to hit the bar and asked where we were headed. He informed me he couldn’t find anyone to go out and asked what I wanted to do. I told him I would hit up my friends and see what I could round up, but I still wanted to go out regardless.
Apparently, it wasn’t going to be just the two of us. I was able to find two friends who were willing to go out, and I told them I would keep them in the loop when I knew what the plan was.
N texted and said he wanted to save some money by pregaming. He asked if he should grab a bottle from the liquor store to replenish some of the liquor he drank at my apartment. I graciously accepted the offer and told him I would see him in a few.
I was two glasses of scotch deep at this point, and my conversation with L was getting quite silly. Not sure why it hit me so fast, considering I can hold my liquor like a champ! After 20 minutes, I texted N asking what was taking him so long. He responded, “Walking out the door now.”
He came by with a bottle of Grey Goose. When he walked in the door, I got a luke-warm hug and a peck on the check, but that was to be expected. It just wasn’t what I was used to. I was also on to my third hefty glass of scotch. The Grey Goose wasn’t all he brought with him. He also brought some recreational supplies. I asked if he wanted to go out on the porch and smoke, but he wasn’t really feeling it. After some arm-twisting, he complied. I don’t know if it was the smoking or the spending time alone with me on the porch he was avoiding, but looking back I’m willing to bet it was the time alone with me.
When we came back in, I plopped down on the couch with another glass of scotch and the rest of the bottle of Johnnie. He sat in a chair rather far from me. L joined us as well after I extended an invitation. I was hoping her presence would help cut the tension.
The three of us sat and chatted while we drank. After some time, N’s roommate joined us. We talked about random things I can’t remember because the scotch began to kick in. At one point, N said something exceptionally person I never knew about him. It really pulled at my heartstrings. All I could think about was how much I wanted to give him a hug. I texted him and said, “You never told me about any of that.” He responded, “We never got that far, and I don’t like normally bringing it up unless it comes up in conversation.”
I asked him if he would come out on the balcony with me. His response: “I don’t mean to be rude, but why?” After that, I lost all the emotional sympathy I was feeling and received his message loud and clear. I said, “Forget it.” Of course, after that, he wanted to know what I wanted to talk about, but I told him to just forget it. We texted each other a few more times while we sat a few feet apart. I was now wasted. One of his texts even said, “You need more ice.”
Since it was getting late, N’s roommate and my roommate went to bed.
After that, everything is a blackout for me. The next thing I remember, I woke up alone and in a panic. It was the next morning, and I couldn’t remember N leaving my apartment that night. He wasn’t in my bed, but I couldn’t for the life of me remember how the night ended. I could hear L outside my door, so I shouted, “Did I do anything dumb last night!?” She told me we were still in the living room when she went to bed, so she had no idea.
I knew I needed to do some damage control. I didn’t know if I did anything inappropriate, but I knew at that point N was the only one who could tell me what happened. I texted him to ask what happened and preemptively apologize if I did anything wrong. I also explained that I had fun just hanging with him and our roommates and added, “Last thing I wanna do is make it uncomfortable…”
He responded, “We made out for a little bit. Then you tried bringing me in the bedroom but I couldn’t… That wouldn’t have been right for either of us.” I slapped myself in the forhead. Of course I did that. I responded, “Thank you for telling me this and thank you for being a gentleman.”
Surprisingly, he replied, “We both knew we wanted to but I couldn’t, especially with you as drunk as you were and I having sobered up.” I thanked him again for being a gentleman, and he countered, “No need to thank me… I’ll always be there for you.” It was a sweet notion. I had a lot of regret for putting us both in that position and was disappointed in myself for acting like a child.
Later that Friday, we talked on Gchat about the events of the night before. It was a very adult and civilized conversation. I was happy for that. We even spoke about what would have happened if I weren’t incapacitated by alcohol. While the conversation was nice, I knew for my own sake, I needed to put more distance between us, or I would never be able to get over him.
As the day progressed, N read my blog again. He read about NC commenting on my ability to do better and was not happy about it. I tried to calm him down, but there was already bad blood between the two. He decided to remove NC from his life and unfriended him on Facebook and blocked him on Gchat.
When 1:00 rolled around, I left work after a half day. I was headed to Belmar at the Jersey Shore with three friends and my sister for the weekend. I was very excited to get away and have some fun. I just got through the week from hell and needed some distractions. I would be free to do whatever and whomever I chose, and that made me very happy!
Follow @onegayatatimeAt the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 
Lazy Morning
Posted by One Gay at a Time in Gay Dating on February 3, 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!
Back to your special edition of One Gay At A Time…
Smiles and I had a very special night together sharing dinner in my apartment. We went to be happily in each other’s arms after being away from each other for some time. I’m not entirely sure why, but I felt he’d finally come around to me.
The massage didn’t last long and the seduction failed to the grumbles of Smiles’ stomach. I should have remembered that was his first priority in the morning.
We sat at the kitchen counter and ate while we chatted a bit about what we had to do the rest of the day. I also caught Smiles up on some of the events going on around the world since he didn’t have cable and wasn’t the best at staying informed.
After breakfast, we returned to my room. I needed to get ready for the office, and Smiles needed to get dressed to head home to begin his workday. We started to make out a bit until I pulled him towards the bed. “Do you want to have sex?” he asked. I giggled with a big grin and replied, “Of course. Why do you think I was trying to seduce you before? I always want sex.” That was also my subtle way of letting him know I wanted to have more sex.
Warning: The following may be too graphic for some. I was already on my back with him on top of me, so I could only assume he wanted to top this time around. I topped the last time, so I only thought it fair to receive this time. I slipped the condom on him as he made a comment questioning whether I was doing it right. “[Smiles]. This isn’t my first condom, obviously,” I quipped.
I was getting very close as I pleasured myself while he penetrated me. Just as I was about to climax, he said, “I going to cum.” I quickly responded, “Me too.” And with that, as close as I was, I was a mile away from finishing. In that split second of him distracting me, I lost it. I could feel my muscles quivering just before he said anything, but it was gone. Now, it was top of mind, and I knew it wasn’t going to happen.
Smiles would have been so happy. He’d wanted to make me finish for so long, and he would have been the first to do so from topping me. Alas, it wasn’t meant to be. When it didn’t, I could see him looking into my eyes with compassion. The sex was great. There was no pain or awkwardness. I wanted to show him how much I enjoyed it, but I couldn’t. My mental block got in the way once again.
After we relaxed and kissed a bit, he suggested we clean up in the shower. He was getting ready to hop in, and I told him I was coming in with him. My shower has two shower heads and a seat. Everyone that has seen my shower has made sexual comments about it, and I was going to finally get some use out of them.
I wanted to have some more sensual time together, and when I hopped in, Smiles began to wash me. I was very turned on by this. When he finished, I tried to do the same for him, but he wasn’t interested. He rinsed off and hopped out of the shower to dry off. I watched him as he toweled off, and immediately got extremely aroused. He put lotion on his face with his towel on the floor while I pleasured myself in the shower at the sight. When he left my bathroom, I beckoned him to come back in the shower and help me finish. I wanted him to be a part of it. He climbed in and I pressed myself against his back while I tried to finish. Once again, failure.
When we ran out of hot water, we hopped out. He finished applying lotion and brushing his teeth while I masturbated on my bed. I needed to finish somehow or work was going to be hell for me! He came and joined me in the crook of one my arms while I pleasured myself. FINALLY, it came. I thought of him dropping the towel in the bathroom, and it set me off. I was disappointed it wasn’t a direct reaction to something Smiles did, but I was relieved he was there to witness that it was possible and that my climax was something pretty special 😉 .
We quickly finished getting ready and walked to the PATH with my roommate chatting the whole way. The conversation wasn’t as free-flowing between us as much as when it was just the two of us. I wondered if Smiles had issues with PDA and public discussion. It just felt a little awkward.
When we got to his stop, I gave him a peck on the lips to say goodbye. I thought about that morning all day. I was happy to finally finish with him in the room, but I wished it came at Smiles’ hand. I think it would have been an ego boost for him and a big step forward for the two of us. However, it was progress — Baby steps. This something I was going to conquer, hopefully with Smiles’ assistance.
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