Posts Tagged dinner
Birthday 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 @onegayatatimeDinner and a Stroll Along the River
Posted by One Gay at a Time in Gay Dating on November 7, 2011
Following my great date with Smiles, I couldn’t get enough. I relished every phone call, every text, every moment I spent with him. I suppose you could say, I was gaga.
Is Smiles the greatest guy out there? Is he the best guy out there for me? Who knows. I don’t know him well enough to make that assumption. However, my appetite was wet, and I wasn’t satiated. He is a really great guy, and possess a lot of the qualities I seek in a man. I was cautiously optimistic — Fingers crossed.
After our last date, I texted, “Had a great time last night btw :)” He responded, “Me too!” That being said, I asked him out once again. The following day, I said, “So… When do I get to see you again?” He proposed Tuesday night. I was a little surprised. I was waiting to hear Wednesday night, since he invited me to his birthday that night. I was thrilled he was interested in seeing me two days in-a-row. I was just hoping he would confirm for me once again he wanted me at his birthday celebration and wasn’t having second thoughts.
I had been apartment hunting, so when I found one, I sent him a picture. That was followed shortly after by a sexy picture of me I took last summer on vacation in California (you’ll recognize part of the picture in my Gravatar on the right). I thought I’d spice things up a little, especially since I promised him I would send the picture. He responded, “That’s way better than an apt pic!” I said, “I thought you’d appreciate…” However, he didn’t believe me when I told him I took the picture with the timer on the camera. He thought someone else took it until I went on to explain the entire situation. “You’re committed to this, huh? LOL. Good for you. Strong work,” he said.
When Tuesday arrived, I asked him if we were still on for that evening. He responded, “Yep. Barring a trip to the hospital for stitches after I punch my computer for not working and wasting my time today.” At the end of the day, he added, “I’ve calmed a bit, looking forward to seeing you. What time are you off? You don’t happen to have running shoes with you? I feel like I need a run, LOL.” After discussing my lack of running equipment, we decided on dinner at his favorite restaurant, Extra Virgin.
We grabbed a table outside the restaurant. It was that time of year right before it’s not too cold to sit outside, but it’s also not quite warm enough to be completely comfortable. We ordered our food and immediately dove into conversation. We talked about our days and what was new in our lives.
He told me he and a friend were going to a shaman to try Ayawaska (a Peruvian root similar to Peyote) for the first time. He explained the setting in a yoga studio and how it works. I was fascinated. I’m certainly not the type to be open to drug abuse, but recreationally or experimentally, I have an open mind, especially if it happens under close supervision. The point was to relax and open you mind. Many people use it to communicate with God/the spirits in a trippy way. There was slight reservation/worry in the back of my mind regarding the whole thing, but he is an adult. I knew he’d be safe.
We ate our meals (I don’t recommend the chicken pot pie at Extra Virgin, but everything else I’ve had is spectacular) and continued our conversation.

Smiles likes to order deserts when we go out. Going out to dinner is already putting a dent in my wallet that normally isn’t there. I cook in my apartment far more often than I dine out. Since I started seeing him, I was going out a lot more often for dinner. Not only that, it wasn’t exactly helping my waistline. It’s amazing how easy it is to put on pounds when you aren’t afraid of people seeing you in a bathing suit anymore.
Instead of getting desert, he suggested we go to this tea shop, McNulty’s and then grab desert elsewhere. He was looking for a specific tea, so I called the shop to make sure they were still open.
After the tea shop, we hit up a gelato place, L’Arte De Gelato. We took out gelato and walked down Christopher Street to the pier. We had a nice stroll along the pier holding hands. I pointed out a few things on the Jersey side, such as the pier I normally hit up in the summer looking back the other way. We chatted a bit at the end of the pier. I was hoping maybe for a little make out session or some hugging, but I didn’t get the feeling he was interested in that. I don’t think he noticed, but when I went to reach for his hand, that’s the exact moment he lifted it from the railing and turned around to head back to the Christopher Street PATH station. I wondered in the back of my head why he never invited me to come back to his apartment, especially since I knew we were in the neighborhood. But, I also know I needed to take it a little slower. I had a tendency to rush things, and I needed to break that habit.
When we reached the PATH station, we hugged, and I gave him a kiss goodnight. I was happy to get to see him again, and I was cautiously looking forward to his birthday the following night. It was an awkward challenge for me, but I knew I was up for it. Birthdays are always interesting situations, especially when you’re the new addition to the crowd, but something told me I’d be alright.
Mom & Dad Turn a Deaf Ear
Posted by One Gay at a Time in Gay Dating on November 3, 2011
Mother’s Day crept up on me this year so quickly I didn’t get a chance to buy Mom a present. It should be easy. It’s always my birthday weekend. I decided quickly, I would take her out to dinner in New York City. I also thought ahead to Father’s Day and suggested they both come stay with me for a weekend. I would take them both out to dinner for Mather’s Day whenever they could find the time to visit. They always look forward to visiting my sister and I in Hoboken and venturing into the city, so I thought it was a perfect gift. I told them to check their calendar and get back to me.
That never really came to fruition. Weeks passed , and they never picked a day. That was the case, until they were coming into the city on a bus trip my aunt was running to see Rent. Every time they come to visit for a show, they go to Carmine’s. I always get an invite to join for dinner or lunch even though I’m not going to the show. This time, my parents wanted nothing to do with Carmine’s. They have a lot of complaints about how my aunt orders a lot of family style pasta dishes. “If we’re coming into New York City, I want something better than pasta, especially at that price,” my mother exclaimed over the phone. I didn’t blame her. The city had a plethora of great restaurants to offer. No one should be going back to the same place every time they visit, no matter how convenient.
I agreed to take them out for dinner following the show and asked them to pick a place. Once again, this was a whole ordeal. I helped them out by picking a few great restaurants in the area to choose from. Even that was like pulling teeth. Finally, they left the decision up to me, so I chose City Lobster and Steak. In the days leading up to the visit, I learned my sister would also be joining us.
I met my sister in Hoboken and rode the bus into the city together. We met my parents at the restaurant and got a nice table by the window. It had been some time since I caught up with my parents, even though I call several times a week just to chat when I’m bored and walking somewhere.
We talked a bit about the show before the topic of conversation shifted elsewhere. At one point, my mother asked me what I’d done over the weekend. I explained my successful date with Smiles and discussed how I finally had a successful third date. “What does that mean?” she replied. I said, “I have had a lot of unsuccessful first dates, but I finally found a guy I liked. In reply, she said, “Oh,” and smiled.
After the ten seconds we spent talking about my love life, she immediately turned to my sister and asked if she was still dating the doctor she had been seeing. I was a little infuriated. This was at least the fourth time she’d done this to me. Every time I brought up a guy I was “dating,” she changed the subject to the guy my sister was dating. She still wasn’t comfortable talking about my dating men. I don’t know why this is. She has gay friends. She’s very accepting of them. Why isn’t she comfortable with mine? I know these things take time. Trust me, I’m not taking that for granted. However, I came out to my parents over a year ago, and they still weren’t quite okay with it. I know I’ve concentrated on my mother’s reaction to this and not my father’s. He didn’t really react much at all. Just head nods. I only single out my mother because this is something I would talk to her about and rarely my father, even if I was dating a woman. I wanted to be able to talk about it with them. It is an exciting part of my life at times. Maybe I need to change that. Maybe I’m not giving him a fair shot. Maybe he could become an ally to bring my mother to terms with my sexuality. Only time will tell.
I discussed this exact exchange with my sister on the bus on the ride into the city. I predicted this would happen when I told her I was going to mention how things were going with Smiles. She suggested I not cause a commotion for dinner considering it was a gift. I explained I wasn’t going to attack them or anything, but I wasn’t going to shy away from the issue anymore. I was going to bring it up, whether they liked it or not.
After dinner, my sister and I went to the bar to meet some of her friends. As we walked, I told her how p*ssed I was. She conveyed I was probably hurt, but I corrected her in that I was p*ssed. She understood. She tried to keep the conversation going when I was talking about Smiles, accentuating the fact that I had gone on so many unsuccessful first dates, and this was a big deal. But, it didn’t exactly work. I asked her to go to bat for me a little. I asked her to tell my parents how disappointed and p*ssed I was about the issue and to ask them why it was happening. It wasn’t an easy conversation to have with them, but I was hoping they’d be a little more forthcoming with my sister, since it wasn’t her feelings they’d be hurting.
Those test results have yet to come back from the lab. In the end, I understand they’re going to have a hard time with it. I would have a hard time if my son came to me and told me he was gay. My heart would go out to him because it’s not an easy lifestyle to live. However, I know it’s not a choice one makes, and I would accept my son completely as the person he is. I would be thrilled he found the confidence to be himself, and I would fully support him and the man he chooses to stand by. I’m not looking for miracles. I just want them to take an interest in my love life. Growing up, they always pressured me to find someone. In a twist of irony, when I finally did, they want nothing to do with it. Only time will tell how this plays out, but when the time comes when I want to bring someone home for a holiday, it’s going to be like ripping off a band-aid, when it could have been an evolving process…
Follow @onegayatatimeSmiles Crosses the Hudson
Posted by One Gay at a Time in Gay Dating on November 2, 2011
After a very successful date with Smiles, I was left wanting more. Of course I was on Cloud 9, but I couldn’t let my crazy flag fly quite yet. I had a great time with him and a connection was obviously there, but I had to check myself. And, I couldn’t put all my eggs in one basket.
Ironically, Smiles showed his hand well before I even had the chance to show mine. Somewhere in the confusion of emails, he replied to an old email I sent him eleven days prior. It was in reference to the first night I met him. I asked him, “How would you feel about meeting up Thurs. happy hourish??” He responded to that email saying, “Done.” He thought I was asking him out again, but in reality, I was asking him out for the first time (the first time we met at Employees Only). I can’t say I wasn’t thrilled with the response. It showed he was as interested in seeing me as I was in seeing him.
Once I realized what happened, I responded to his email, and now that I had his number, I sent him a text: “While I may jump the gun when it comes to emailing you, you’re the complete opposite. You ask yourself out and respond to emails a week old. I asked you to go out for happy hour 2 Thurs. ago, not this coming Thurs. I can’t meet up this Thurs. I have volleyball, but I’d love to meet up Fri. if you’re available.”
He laughed at the situation and told me we’d make plans for Friday after work. When Friday arrived, I texted him and said, “What’s the plan?”
He responded, “I was thinking it might be fun to go to the Standard Beer Garden for a drink and play ping-pong then go up to deem for new or since I haven’t really been to Hoboken, grab the PATH from the village afterward and find dinner somewhere over there. Thoughts? Preferences?”
Obviously autocorrect was hard at work here. I had no idea what “deem for new” was, however, that wasn’t what I was concentrating on. The fact that he offered to come to Hoboken spoke volumes to me. When I started dating guys in the city, I knew I was going to have to be the one to commute in. No guys in the city like to come out to Hoboken. They think it’s this far off land, when really it’s easier than going over to the East Side.
“Beer Garden and ping-pong sound great. Hope you bring your A game 😉 Don’t know what “deem for new” is, but we can hit up Hoboken too…” I responded.
He replied, “Harlem for bbq. I hate this autocorrect. Just give me my keyboard back.”
We met right after work and had a few beers. When the ping-pong tables opened up, we hopped on. I love an active guy. I have a short attention span and love being active, so when I find another guy who’s on the same page, I find it incredibly sexy. After about a half hour of rallying back n’ forth, we finished our beers and chatted a bit. When both our glasses were empty, we discussed where to head next for dinner. Since he offered to go to Hoboken, I capitalized on that opportunity.
As we walked to the Christopher Street PATH station, he pulled me aside and planted a kiss on me. This was starting to become a pattern, and I LOVED IT! I’m not big on PDA, but when you can sneak a kiss when no one is around on the street, I get incredibly turned on. I’m not gonna lie. When I knew we were going back to Hoboken, I had a pretty sure feeling we’d be visiting my apartment at some point in the night.
We took the PATH to Hoboken and joked about the many characters riding the train. This was a new experience for him. That’s what he was looking for, either in Hoboken or Harlem.
When we arrived in Hoboken, I showed him the amazing train station. He is big on photography and architecture, so I knew he’d appreciate it. Afterwards, we took a stroll along the waterfront as I pointed out the spectacular view of New York City. He reached out and grabbed my hand. This was a completely new thing for me. I’d never held a man’s hand in Hoboken. It’s not a homophobic society, but it’s also not a very open one. Regardless, I loved the sign of affection.
We decided to have dinner at Zylo, the steakhouse in the bottom of the W. Neither of us had been there, so we decided to give it a whirl.
While we sat at dinner we chatted. We ordered drinks; of course the same since we share drink tastes, but this time it was dirty martinis with bleu cheese olives. I was nearly floored when he brought up his birthday festivities and invited me. “I’m having my birthday on Wednesday with two of my friends at The Jimmy if you’re available and would like to come.” I told him as long as I didn’t have anything else going on, I would be thrilled. That was a huge step for me. The birthday invite is no small potatoes. It’s a big deal. It means introducing me to friends. I was impressed he felt that comfortable with me already. I wondered if I would get an invite since he first mentioned his birthday. I immediately became more attracted to him and started to let my guard down a bit. I didn’t need to put up such a front about my true feelings.

After dinner, we walked outside. I grabbed him and said, “Okay. So, I’m not going to let you come all the way out to Hoboken without coming to my apartment. You up for that?” He agreed, and we set off in the drizzling rain towards my apartment. Of course, he complained about the distance, but I assured him it would be worth it in the end.
When we got to my place, I showed him around, of course ending in my bedroom. It didn’t take long before animal instincts took over, and we were all over each other.
(Warning: Following paragraph may be too graphic for some) In the midst of passion, with the lights off, he said to me, “I want to f*ck you so bad. Are you okay with that?” I had a decision to make. All summer, I lived by the policy of strictly topping. I found I did not enjoy bottoming and declared that was something I would only do for a guy I truly liked once I was in a relationship. This policy worked quite well for me, but again, I had a decision to make. Without a word, I reach into my nightstand and took out a condom and bottle of lube. The decsion was made. I handed him the condom and warned him he’d have to go slow. It had been a long time for me since my last penetration. As I’ve experienced many times with guys, “condom syndrome” kicked in, and the heat was lost momentarily. However, we quickly recovered and some great sex ensued.
Afterwards, we showered and hopped into bed for the night. After a little cuddling, we both dozed off. In the morning, I woke and went into the kitchen to make us breakfast. Shortly thereafter, he woke and came out to join me. I loved seeing him walking around in my clothes.
I poured him a cup of coffee and went back to the stove to tend to the eggs and homemade pork and apple sausages. He came behind me and gave me a hug and kissed my neck. It was the perfect gesture at the perfect time. I was really falling for him every second I spent with him. This is what I’d been searching so long for. I was happy with where things were going, but that doesn’t mean there wasn’t still a little doubt in my mind. We weren’t dating yet. As my friend loves to point out, sex does not equal a relationship. She is right.
After we ate, I walked him back to the PATH. It was Saturday afternoon, and all of Hoboken was out getting ready for the football game. We stopped in front of the PATH station, right across from the prominent football bar, Texas Arizona, and we kissed each other goodbye. Again, this is not part of my comfort zone, but I went with it. I needed to be comfortable with these situations. There is no reason I should be embarrassed or ashamed.
Needless to say, I walked home with a grin on my face from ear-to-ear. I was so elated and blissfully happy. The date could not have gone better. However, there was a little voice in the back of my head telling me to calm down and not get overly excited…
Follow @onegayatatimeWall Street Dining
Posted by One Gay at a Time in Gay Dating on October 31, 2011
My apologies. After a short hiatus, I’m back…
In the days following my date with Smiles, I was very happy. I felt I finally met a guy I was really interested in who was genuinely interested in me. The possibilities seemed endless.
That being said, we weren’t dating yet — Not even in my warped head. There was no reason why I shouldn’t still be seeing other guys. Before I met Smiles, there were a few guys I was trying to set up dates with while I was building up the roster.
One in particular worked in a different part of town than I worked in. He was down in the financial district on Wall Street working as a consultant. While New York City isn’t exactly long distance dating, I definitely have a predilection for guys who live/work near where I live and work. It just makes it more convenient to see each other.
If you recall, my only real relationship that had two legs to stand on was with Broadway, and we rarely saw each other outside the bedroom based on work schedules. I know myself well enough to know I need a guy who will be around and able to spend time with me.
That being said, this new guy wasn’t eliminated because he was a subway ride away. Like I always say, I’m an equal opportunity dater. I don’t discriminate, even based on location.
We finally found an evening to meet up for dinner after I was done work. When the day arrived, he had quite a busy schedule, but he was still able to step away from the office to grab a quick bite. He picked a restaurant near his office, Plein Sud. It was convenient for me because it was a few blocks away from the World Trade Center PATH station for me to scoot home. I arrived slightly early and waited for him to arrive. He was running a little behind. I didn’t mind because usually I am the one running late.

When he arrived, we went in and sat. It was a nice French restaurant. I was expecting something a little more casual, but I went with it.
We met on OKCupid. He checked out my profile and messaged me. We went back-and-forth a few times before deciding to try to meet up. We had an active lifestyle in common, so I was willing to meet him without first getting to know each other in-depth over the computer. I wanted to make sure we had plenty to talk about on the first date, even if it wasn’t going very well.
We sat and chatted a bit about our jobs. To be honest, I didn’t remember a whole lot about him, but he didn’t recall everything about me either. After discussing what we did to pay the bills, we moved on to where we grew up and where we went to school. He was from Mexico/Texas and still had a thick accent. We had quite a different upbringing and studied very different fields in college. He was a nice enough guy, but we didn’t share all that much in common after all. We talked shortly about what we do for fun before he asked the waiter for the check. Throughout the meal, he kept apologizing for having to make it so quick, but I understood he had to go back to work. There weren’t exactly fireworks between us, so he wasn’t preventing a good thing from continuing.
I can’t know what was going on in his head, but he seemed interested in me and asked if we could meet up again. I told him, “I’m sure we can work something out.” I knew in the back of my head I was never going to see this guy again. He was a nice guy, but I could already tell it would be laborious to find time to get together. Finding friends/lovers shouldn’t be that hard.
I said goodbye to him at the corner as he walked back to work, and I walked to the PATH.
I was okay the date didn’t go spectacularly. I had my sights set on Smiles. However, I know myself well enough, and I still needed a distraction so I wouldn’t smother him with attention. I continued to look to my roster for dates, but that’s also where The Principal came in. We continued to talk on the phone, text and chat. I needed an outlet, and we already had a budding relationship. I would continue to foster things with him while I investigated the furthering of a relationship with Smiles.
Follow @onegayatatimeSmiles Returns
Posted by One Gay at a Time in Gay Dating on October 19, 2011
While returning home from alumni weekend, I sent an email to Smiles to see if we could find time to get together Sunday afternoon: “Hey dude. Let me know if you’re still up for meeting up tomorrow…” I sent it around 11:00 at night, so I didn’t expect a reply until the following day. So, when I got back to Hoboken, I asked around to see who was going out to the bar. No one seemed to be up for anything, so I went home did laundry and watched TV.
I woke the next morning to a return email from him saying, “Hey bud, yeah we can work something out. What did you have in mind?” I replied back, “Your call… Grab bite, drink, coffee, walk High Line…” Apparently, he was already out and about that morning, and he responded, “Just finishing brunch. Let’s grab cords and walk up highland. What time works?”
I was a little confused, but I was used to deciphering autocorrect text messages. “I’m assuming that cords means coffee and highland means highline… haha I can meet you in about an hour? That work?” I responded. He replied, “Ah yes autocorrect. Let’s meet at 4:30 at Doma in west village its 7th and Perry I think.”
I was very excited but still very relaxed. I was thrilled he was still willing to see me again after the less that stellar first date, but I’ve also done a very good job of not getting my hopes up about these dates anymore. I’ve had enough bad ones to know the drill now. Yes, I’ve become jaded.
I arrived at the coffee shop and waited for him outside. When he arrived, we exchanged hugs and went inside to grab coffees. He paid for mine, which I thought was very sweet of him. He suggested we take a walk through the West Village on our way to hop up on the High Line park. As we walked, he told me about the crazy time he had the previous night at the bars and how he was a little less than 100%. He put his arm around me and explained he was afraid to postpone on me since I was so broken-hearted when he didn’t respond within the first twelve hours after our first date (in a playful way). I was a little embarrassed by my lack of patience and told him he could have postponed on me, and I completely would have understood. We had a good laugh about it.
We walked and came upon a band playing in a courtyard. We stopped to listen before continuing on to the High Line. We climbed the stairs to the elevated park and began to stroll along like everyone else. This was the third date I took up there. I could tell Smiles was really enjoying it. He is very interested in architecture and design, as am I, so we had extensive conversations about all the surrounding buildings. I found it utterly romantic when he would turn my attention to a specific building by putting his hand on my shoulder to talk about a specific element. We talked the entire span from 14th street to 34th street. We even passed Joan Rivers and her small entourage while walking. When we reached the top, we walked back down to street level.
As we walked back downtown, we talked more. I learned he attended three different Burning Mans in the past. Just that Friday, I watched a movie shot by a bunch of guys who attended this years. It looked spectacular, and I was highly interested in attending. He gave me some of the insider tips, and the conversation shifted to the traveling we’ve done.
As we were walking through the West Village again, he noted he’d love to grab a beer and asked if I was interested. We stepped into a nice spot that had an outdoor space in the back, Entwine. We both ordered sangria. When I mentioned I wanted to order hummus and pitas, he noted he had to cut gluten out of his diet. I was rather famished, and I think he realized this.
He originally planned to meet his ex for dinner that night, but hadn’t heard from him in some time. Since this was the case, he asked if I would be interested in grabbing dinner with him. Of course I obliged. He mentioned two spots he could think of. I agreed Extra Virgin sounded great. He warned me he was quite the regular at that spot, but I wasn’t quite sure why that warranted a warning.
I paid the tab for the sangrias, and we started to walk to Extra Virgin. The night was shaping up to be quite a date, but it was only just beginning…
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Posted by One Gay at a Time in Gay Dating on October 4, 2011
Starting the final Friday of my vacation, I began talking to a very interesting man on the mainland of Massachusetts. Right off the bat we clicked. Of course, I found him on Grindr, but that doesn’t mean he isn’t a man of quality.
I tried my hardest to convince him to visit me. I suggested we grab a drink and/or dinner. We went back-and-forth on the issue, and of course, I ultimately lost. No matter how hard I tried, he would not get on a ferry. Even after offering my bed following his question of where he would sleep, there was no convincing him. I went as far as to pull a shirtless picrture out of my arsenal. No dice.
But that didn’t deter me. We spoke every day of the rest of my trip. I enjoyed his messages. I enjoyed the cat-and-mouse game we played. When the time came to drive home, I turned to him to entertain me for the long car ride. We started messaging each other the second I hopped on that ferry. Had I been in charge of my own transportation, I would have made a detour on the way home, but that wasn’t an option for me.
Instead we took the oppotunity to get to know each other over five-and-a-half hours. I learned about his job as an elementary school principal. I enjoyed picturing him with a myriad of children circling around him. I remembered how much respect I had for my principal growing up. It was fun to picture the little tykes looking up to him. I learned he swam in high school and coached a team as well, but he had to give it up when he left the classroom for the principal’s office.
When we stopped at a gas station, I surprised him by calling for the first time. It was great to hear his voice. He never expected me to pick up the phone and call, but after talking to him for three days, I thought it was time to speak to him instead of just texting. The conversation was short, but it was special.
Once we got back on the road, it was back to texting. Periodically, I would switch back to some of the other guys on Grindr, but I didn’t have much interest in them. They lived in Rhode Island, Connecticut, etc. It was crazy enough I was trying to continue the conversation with someone in northern Massachusetts.
However, I learned one thing when I was working things out with San Francisco from across the U.S. You can find ways to make a long distance relationship work, but certain understandings need to be met. Both parties need to be willing to put in great effort to make it work, and an end game needs to be discussed at some point.
My mainlander continued to point out how ridiculous it was for us to be talking. He was very skeptical of the whole thing. I tried my hardest to get him to open up. I told him, “I’m not thinking about that bridge until I come to it. Right now I’m just enjoying chatting with you. Does it make sense to do this? No. But could it be something special? Only time would tell. But, it’s sure to fail if you don’t give it a chance to even begin.”
With every word, I found myself falling for what I pictured this man to be. I proceeded with caution, but I was also diving in full force to explore the possibilities of where our conversation could go.
When I arrived home, the conversation ended for the day. I was preoccupied with other men, but that doesn’t mean the conversation between us ended at that moment. I liked everything I was discovering thus far, but there was much more digging to be done…
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