Posts Tagged OKCupid
Not Tired of Me Yet?
Posted by One Gay at a Time in Gay Dating on March 16, 2012
Apologies for all you who got my draft post sent out today. I didn’t realize I had it scheduled for release before finishing it. Please disregard! And apologies for the late post today.
Back to your regularly scheduled program.
So last we left off, my Grindr friend/neighbor, who I will now call PR (short for Puerto Rican), and I were making out on my chair in my living room after a night at the bars and some Cluck U chicken.
I’m sure you’ve been wondering what happened next. Well..
After some making out, I grabbed his hand and led him to my bedroom. We had our fun letting our hands explore the other’s body. Things escalated from there until we finally dozed off for the night. He wasn’t the sexiest guy to enter my room, but we certainly had a good time together. I really enjoyed cuddling and making out with him, as well as many other things we experienced that night.
When we woke in the morning, we didn’t get out of bed. We spent a majority of the afternoon laying there spooning and cuddling and just talking. I really liked how frank he was about things. He didn’t sugar coat or try to impress me. He was being real. This is a quality I seek out in men. It’s very important.
After some time, he asked the question I knew was coming, “Soooo, are you a top or bottom?” I told him I was a top. I quickly learned he too was a top. This, of course, was followed by a long awkward pause on both our parts. I wondered in the back of my head if he was convertible. He told me it was nine years since the last time he’d done it. That left a glimmer of hope that he had done it in the past, however, nine years is a long time! Maybe this was doomed before it even got off the ground. Maybe we were simply sexually incompatible. But, I liked him. I wasn’t ready to walk away from it just based on this.
After more chatting, we started to fool around some more. Warning: The following may be too graphic for some. We orally pleased each other for some time. He felt so good. Finally, we finished ourselves off laying next to each other. It took some time for both of us. When we did, he mentioned how it takes him a long time to finish. I kissed him strongly. I told him how good it was to hear him say that since we both shared that “malady.” I was happy he was understanding.
Around 1:00, we finally got out of bed. I offered to make him breakfast. I cooked up some of my homemade sausage, eggs, avocado, English muffins, coffee, etc. This was serving as our lunch and our breakfast. We watched some TV on the couch while we ate.
Finally, he decided to head home and get ready. We made plans to go out for dinner that night. I had a Living Social I was ready to burn up at Trinity, a nice restaurant on the Hoboken waterfront.
Around 6:00, I met him on the street corner between my apartment and his friend’s apartment where he was staying for the time being. We took a leisurely stroll towards the waterfront, talking the whole way. When we arrived at the restaurant, it was closed for a private event. We decided to go elsewhere rather than wait for dinner because we were both starving. He wanted to go to East L.A. for margaritas. It sounded like a good plan, so I agreed on that.
That night, he had plans to go see a movie with one of his friends. His friend wasn’t getting back to him, so he asked if I wanted to go instead. It wasn’t a movie I was looking forward to seeing, but I had no plans and was enjoying spending time with him. I agreed to go. We talked about many other things over dinner, including the other gay date we were sitting next to. The two guys were younger and we could tell it was a date by what we saw and heard. It was very cute to see — Not something you see every day in Hoboken.
When we finished dinner, we started walking down the street towards our apartments. He decided against the movie since he was tired, so we agreed to just stay in and watch TV instead. I’d never seen the Paranormal movies, and he liked them. We decided to make a Paranormal Activity marathon night of it. We snuggled on the couch the entire night. I was very happy being in his arms, and he in mine.
When the movies were over, it was late. We decided to just go to bed, and I asked him to stay the night…
Follow @onegayatatimeHighs and Lows
Posted by One Gay at a Time in Gay Dating on February 24, 2012
I had been on OKCupid only a short while before I met Smiles. I met only one person from the site, LES, and that was already after I met Smiles. I have to say, I’m not that big a fan. Every search I did produced few candidates I was willing to entertain. No one was good-looking, and no one had exciting profiles. It reaffirmed for me why I originally was so against dating sites. I felt like it was full of desperate men.
Rarely would I receive a message for a worthy candidate, but when I did, I would quickly respond and dry to stir up some dialogue.
I started chatting with a nice southern boy from North Carolina who moved to the city in the previous few months. He seemed like a really genuine guy who wasn’t into the scene or fully out. I was very attracted to that. The southern boys always brought a little extra something I always liked. They were mannered and real men.
We messaged back and forth on OKCupid for some time before we exchanged phone numbers. One night, he asked if I could chat. I asked him for his gchat or AIM name. He responded, “No. I meant on the phone.” To which I responded, “Sure.” We spoke on the phone for an hour that night. I really got to learn a lot about him. He was volunteering a lot of information about his upbringing and his company and where he is today. He told me how he hates gay bars. He even took the time to tell me about his “hetero life partner.” That’s what he calls his best friend and roommate he left behind in North Carolina when he moved up here. Apparently they were completely best buds, however, nothing sexual ever transpired between the two of them. It was sexy to hear him speak about such a masculine love with his friend. I was really liking what I was hearing, and the fact that he wanted to call gave him so many bonus points in my book. I even told him that last bit of information, which I think he really appreciated.
In the morning, things switched to texting. He was horny and asked me to send him some more risqué pictures. I was onboard. I was all the more happy he asked actually. It proved to me he had a healthy libido, especially in the morning, which is when I’m at my horniest. We exchanged a few racier pictures and went to work. We made a commitment to each other to try to find some time to go out on a date in the near future. I couldn’t wait. He was not only sexy to look at and hopefully to touch, but he was also sexy and masculine in his personality.
In the meantime, I was also talking to a guy I met on adam4adam.com who I’d been messaging on and off for over a year. Between every relationship, this guy and I would exchanges flirty messages and pictures, but nothing would ever transpire. It was so frustrating because I found him to be very hot. He’d get very flirtatious, but never follow through or agree to meet me. Now I was making some ground. This time around, he seemed genuinely interested. I’m not sure what changed, but I was going with it. He was coming back home after a weekend away, and we were texting the entire ride back. When he got home, we continued the conversation on Facebook with a lot of banter and playfulness. He was really coming around on me. I continued to propose a date, but it wasn’t the easiest. He was open to the idea, but I couldn’t get him to lock down on a specific time and location.
A lot of our conversations revolved around sex. Again, after the dry spell I went through with Smiles, I was happy to hear it. I also knew he had a great job, as he had his doctorate and was using to teach at a college and work at a clinic. He really seemed like the full package. From looking at his Facebook pictures, I could tell he loved to travel and he loved to have a good time. He also lived close to me. I felt like this time, I had it in the bag.
That night, I found a guy on Grindr. He was visiting, and the host he was staying with was away. He knew no one and wanted to go out. I was already contemplating going out, so I convinced my roommate to join us at the bar for casual drinks. We met him on the walk to the bar, and when we did, I was shocked. He was tiny. I’m 6’2″, and he was easily 5’2″. My roommate immediately whispered a comment to me. Then he opened his mouth and the queeniest voice came out. I was so turned off, but I couldn’t be rude.
We awkwardly sat and chatted at my favorite bar that night. It was dead, so there wasn’t even anything to distract from the incompatibility. When my roommate and I had our fill, we decided to head home. The little munchkin followed us home. He asked if he could come over, and I agreed. It was a moment of weakness. I was horny, and I thought he could be fun.
BOY WAS I WRONG. He was beyond a stage five clinger. After some making out and heavy petting, he spent the night. The next morning, he told me the only way we could have sex is if I could see him the next night. Foolishly, I agreed. It was bad. No. Let me rephrase. It was awful! I couldn’t get rid of him fast enough. I kept laying it on thick how much I needed to get to work, and finally I scooted him out the door.
This was just gay karma coming back to bite me in the ass. I never should have led him on. From the bar, I should have had the balls to just send him home and take care of myself. This is where my penis gets me into trouble. Soon enough, he’ll learn his lesson…
Follow @onegayatatimeKeeping His Options Open
Posted by One Gay at a Time in Gay Dating on February 23, 2012
Well before I met Smiles, I had been chatting with a guy I met on Grindr for some time. He was a feisty one, and I had a hard time locking him down for a date.
One thing you should know about me. If you ever give me your number, count on me having it forever. I don’t delete anyone. Whenever I add someone new from Adam4adam.com, Grindr, Manhunt or OKCupid, I note in their name how I met them. I ask them immediately to send me a pic to attach to the profile so I can keep them straight. If I meet them and don’t think there is potential or I find they aren’t worth my time, I add an X in front of their name so they go to the bottom of my contact list. It’s a system I’ve developed, and it works quite well.
When I broke up with Smiles, I went back through all the guys I hadn’t Xed. It certainly wasn’t a long list, and I’m sure the guys had long forgotten about me. However, it was worth a shot. I had nothing to lose. I’d simply remind them who I was. If they were still interested, great! Mr. Feisty was among this company.
Surprisingly, when I reminded him of who I was, his tone was very different from the last we texted. He was much more open to meeting me and far more playful than three months prior. We got caught up on what was going on over the past three months over text.
I did learn that he met someone in December, and they’d been dating since. However, he was willing to meet up for a drink as friends.
Now, I know he said we’d meet as just friends, but that’s not what he really meant, I’m sure. He was keeping his options open. He wanted to manage my expectations going into our “date,” but he was also leaving himself the opportunity if he liked me to see me again. I was okay with all this and was certainly up for the challenge. My game face was on. Now we were introducing something into the dating game I’d missed from my life since I swam in college — Competition. I could put up a fight with the best of them. I was going to show him how great of a guy I was, and he was going to like it.
He’d been traveling that weekend, and I happened to catch him on his way back into the city in the car from south Jersey. We went back and forth for quite some time. I was once again shocked at the night-and-day difference in his correspondences from the last time we chatted. We figured out a night to grab a drink after work. I went down to meet him in the West Village at Jeffery’s Grocery.
When I arrived, he was wearing a baseball cap and no glasses. This was quite different from the picture he’d sent me. The reason I kept trying to talk to him so much was because the picture was very sexy. I found him very attractive. The man standing before me was attractive, but not like the picture.
We both ordered a beer. He’d chosen one of those odd places that has beers on tap I’d never heard of. I had no idea what color my beer was going to come in. The conversation was tough to break into. He wasn’t being very friendly. If anything, he was being combative. I got the feeling he was being defensive the whole time like he was getting a bad review at work. He never added much to the conversation. He would answer my question fully, but never sparked the next topic of conversation. It was very uncomfortable.
At one point the topic of Facebook came up. He went off! To say he hates it is an understatement. He loathes it, and made it quite known. But, somehow me managed to spare me from being a part of the idiots whining about their lives on there. Somehow I wasn’t one of the, and I wasn’t supposed to be insulted. I respected his opinion of the site, but he didn’t respect mine. He just seemed so angry. I was so turned off and couldn’t wait to leave.
We talked about the dating world. Usually on a date when you start to talk about the physical act of dating, you’ve reached the end. There’s nothing to talk about between you anymore. If you reach this topic, it’s because the only thing you have in common is that you’re doing this with many other people who it didn’t work with either. He told me about a few of his long-term partners. I was jealous he was able to find guys he could call his partner — and more than one. I told him about my worst date ever (until this one), and he couldn’t believe I didn’t leave. He told me he wouldn’t have had the patience to last five minutes with the guy.
However, it was obvious he wasn’t interested in me. That was evidently clear when the bartender asked if we’d like another, and he said he was done. This date wasn’t even entertaining. It was simply painful. I got absolutely nothing out of it beyond the knowledge I wanted nothing to do with this guy.
We paid our tab and left. We were heading in the same direction, so we walked together a block, said our goodbyes, and I walked away never looking back…
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Boston Therapy
Posted by One Gay at a Time in Gay Dating on February 21, 2012
My relationship with Smiles had come to a close. We met. We discussed. I guess you could say we had closure.
I’d already moved on to other men and began rebuilding my roster. It’d been a while since I was in the game, and I was a little intimidated. Over the three months I dated Smiles I lost my edge. It was my sister who pointed out to me, “I didn’t like you with him. You weren’t yourself. You were much more reserved around him.” I didn’t like the sound of that. I pride myself on being open and myself all the time. Apparently, I lost that somewhere along the way. I needed to find it again.
I would do so with the help of my therapist, Boston. I really lucked out in my timing. Boston was on a break from his final year of school, which meant his services were available. I was going to take full advantage. He was a good friend, and I missed him. I was really disappointed we didn’t get to meet up when he came to visit New York for New Years. It really made me look forward to the day when he graduates, and I convince he to come to New York or Hoboken so I can have him around more often.
Monday night when I got home from work, I called Boston. I wanted to give him an update on how everything with Smiles went since we’d been chatting about it a bit. I told him how everything ended and how I was moving on.
Ironically enough, Boston had a few tales of his own. Apparently, a little of me was rubbing off on him. I was very happy to hear this news. Sometimes I think he puts his love life on the back burner too much. I think he loses hope at times and engulfs himself in other ventures. I want to see him happy. He’s a great guy and he deserves this.
So, when he told me about a straight friend of a friend coming to visit and the sub sequential hookup that ensued, I was downright proud. He managed to attract a “straight” man enough that this man took the opportunity to make out in the bathroom of a club.
I was so happy to have my friend back. I loved swapping stories with him!
I also took the time to explain to him how LES wouldn’t talk to me. For the life of me, I couldn’t figure out what I could have done to him to make him stop talking to me all of a sudden. We were building a strong friendship. I had the feeling he developed feelings for me, especially since he asked me, “So what’s the deal with [Smiles]?” He invited me to his birthday, and I missed it. I apologized, and he told me it was okay. I invited him to my holiday party, but he dropped off the face of the earth and never showed. Following, I attempted to reach out to him on numerous occasions. Okay, so maybe I’m under exaggerating. I tried to text or call almost every day for a while there. I thought I was being funny, but now looking back, I could easily see my actions being misconstrued. Maybe he thought I had stalker tendancies.
In the end, things got very suspicious. He would never respond to my Facebook messages, and he never showed up as online. However, he never unfriended me. As long as that didn’t happen, I didn’t think he was all the annoyed by me. I sent him another long apologetic message on Facebook asking him to please reach out to me. When I finished writing it, I thought I’d give him a call to see if I could get through. It’d been about a month since I last texted or called. When I did, I was shocked to find out the number was no longer in service. He either blocked my number or changed his.
I couldn’t believe it. Had I really taken it that far. Maybe he wasn’t mad at me. Maybe he was afraid of me. I hung up the phone and immediately sent another Facebook message: “I’m sorry if I’ve been bothering you. Don’t worry. It won’t happen anymore.” I was mortified. Did he really think I was that insane, or was he really that mad at me. I was really hurt that someone would ever be that mad or upset with me that they’d simply cut me off. My ego was seriously bruised.I also happened to be perusing my old messages on OKCupid, and it told me LES deleted his account. When I made a new OKCupid account shedding an identity I’d used since college, I came to realize he was still on there and had an updated and active account. He’d blocked me on there as well. He really wanted nothing to do with me, and there was nothing I could do about it.
“You can be a bit aggressive,” Boston told me. That really resonated with me. I did tend to be agressive. I’m a tenacious man. When I see something I want, I don’t give up until I attain it — This goes for everything.
The interesting part was that I simply wanted a good friend back. He was a really fun guy to be around, and I wanted to introduce him to Boston. I thought they’d make a GREAT pair. I would have loved to see the two of them together. But, I don’t think that will ever happen. New York is a big city, and I don’t know that we’ll ever cross paths again.
Boston and I talked more over the course of the week. We almost had a nightly check in for a while there. We’d chat on the phone for about an hour about our dating lives and the mistakes I made with Smiles. He told me more stories about another guy he was helping to introduce to the gay world. I hope I’m not blowing up Boston’s spot, but once again I was proud of him. He was facing new challenges and having new experiences. I was happy to see my friend experiencing more of life these days. I understood how busy school made him, but at least he was taking advantage of his time off.
I was building my roster and had a friend to gossip about all the new things going on in my life. Things were getting better, but I still wasn’t happy to be back out in the dating pool. I was anxious to land another man, but this time around, I wasn’t going to just settle for a guy who was willing to date me. I needed to “find a man who will worship you like you worship him,” as my friend A so eloquently put it. I needed a real man, not another little boy. A man who could express himself verbally, emotionally and physically. I was going to find a triple threat, and once again I had one of my closest friends in my corner.
Follow @onegayatatimeLast Minute Regrets
Posted by One Gay at a Time in Gay Dating on December 9, 2011
After my awkward date with Smiles, I felt I needed some change. The date was uncomfortable and the goodbye was lack luster.
Two guys had been reaching out to me on OKCupid, so I took the time to respond to them and try to set up a time to grab drinks. I shot them a text to see if they was available the following evening.
One of them, a guy who happened to go to the same college as me, responded informing me Wednesdays were the only day during the week that really worked for him. He was taking graduate courses, so he was quite busy.
The other guy texted me back to explain he was most likely available to meet for a drink when he finished work, but was unsure when that would be. He is a financial planner, so his hours are somewhat sporadic. We planned to touch base again at 5:00 the next day.
I had a lot of regret after setting up this date, but I tried to proceed with an open mind. All my friends encouraged me to date more people and not put all my eggs in one basket. I was finally following their advice. Smiles wasn’t exactly being the warmest towards me, so no harm, no foul.
When 5:00 arrived, the regret came flooding in. I didn’t want to meet up for drinks. I felt like I was cheating on Smiles. The planner sent me a text explaining he would be working late. He asked if I could meet for coffee at 9:30. I agreed, and sat with my guilt. It was already bothering me, and I didn’t even go out for the drinks yet. What if he tried to kiss me? What if he really liked me? What if I really liked him? This just goes to show you shouldn’t make quick irrational decisions.
As it got later, I got more nervous about the date. Not because of the date, but because of what it would mean for Smiles and I. I didn’t want to betray him. We hadn’t talked about exclusivity yet, but I was hoping we were moving in that direction.
I received a text that calmed my nerves completely. He had to cancel because he got called back into work. I was off the hook. I’m very grateful he cancelled on me, because the guilt would have really gotten to me. It’s just who I am.
I began to examine my relationship with Smiles. There were times he was completely affectionate and a total sweetheart. He really made me happy during those times. Probably far more than he realizes. I really enjoyed spending time with him, no matter what we were doing. On the other hand, when he would ignore me or not take me into consideration, I felt like such a small man. It really hurt to feel he wasn’t feeling about me the same way I was feeling about him. I wanted him to adore me the way I adored him at times. I felt like he always kept me at a safe distance. Not so far that I leave him, but not too close that I could ever hurt him. If we were going to proceed together, he was going to have to make himself more vulnerable and let me in.
I felt like I was part of his second life. He had his friends and acted one way with them, but when he was with me, he was different. He never integrated the two lives. Always separate. This is the reason I broke up with Broadway.
All this also helped me realize I needed Boston back in my life to talk me out of these crazy ideas. He is my sanity. I let my mind run wild after one bad date. He was always someone who could put me back on track and give me a strong dose of reality, not what my mind was conjuring up. However, he isn’t the easiest to get ahold of since he’s in he final year of school.
Smiles wasn’t talking to me much, so I would wait until he felt the need to talk to me. I didn’t go on the date, but I wasn’t exactly running back into Smiles’ arms. I was going to play hard to get a little bit…
Follow @onegayatatimeAwkward Silence
Posted by One Gay at a Time in Gay Dating on December 8, 2011
Yet another video I’d like to share. This one is a music video for one of my new favorite groups, Duck Sauce. Great song and love the sexual connotations, but may not be safe for work depending on what you do. Enjoy!
On with the story…
Every Tuesday in Hoboken is free movie night if you have Cablevision’s triple play. I do not, but I have some very generous friends who do, and they lend me their card when they’re not using it.
I asked Smiles if he wanted to catch a movie and dinner. He told me he could possibly do dinner, but there was no way he could do the movie. He had to be up at 6:30 the following morning for a work meeting, so spending the night in my bed was off the table.
While I was finishing up work, he was moving his final boxes into his storage unit from Harlem. I agreed to help him when I arrived downtown, but when I got there, he was already finished.
I walked him back to his apartment. We talked about his day on the walk. I waited while he showered and changed after loading and unloading all those boxes to go to dinner.
While he was moving the boxes, both his parents called, separately. He was a little worried, so on the way to the restaurant, he dialed his mother. Smiles said he needed to walk a while, so we kinda just went for a stroll. We talked a little about work and how he got to where he is today. We stopped in a few stores on the way. We were walking for over a half hour before we settled on a spot to grab some grub.
We settled on Peels. When he returned to the table after washing his hands, the conversation was very dry. There were many long awkward pauses throughout the night. I struggled to think about anything we could to talk about. Nothing. I didn’t know what to do. We continued to eat in silence. It was incredibly awkward. I was so worried we’d hit that point already where we had nothing to talk about. I was petrified.
Was he distracted by the phone calls? Did something happen? Who knows?
When we finished eating, we paid the bill and began walking back toward his place and the PATH. We ran into a friend along the way, and Smiles chatted with him for a short while after barely introducing me. After we left the friend, he explained who he was and how close a friend he is. I was a little surprised. If he was such a good friend, then why was he so casual when introducing me. Maybe I didn’t mean as much to him as he did to me. Maybe I was putting too much of myself out there too soon. We’d been dating for a month and a half. I thought we’d be closer knit at this point, but maybe I was wrong. Maybe I had different expectations.
As we walked, he told me he was tired and a bit out of it. This wasn’t news to me after the awkward dinner we just had. He walked me to a crossroad and said goodbye. When I went in for a kiss, I barely received anything in return. It was almost like a child begrudgingly accepting a kiss from a grandparent. I felt like a piece of sh*t.
As I walked by myself to the PATH, I wondered if this thing had run its course. How much longer were we going to go before he fully opened up to me? — Before I didn’t have to wonder where I stood with him? I was tired of the uncertainty. It was dragging me down.
I needed to talk to someone, so I called Boston. No answer as usual. College always gets in the way of our friendship!
Next, I called LES to see what he was up to. No answer, so I left a message.
Then I texted the Principal just to say hi and see how he was doing. When I came above ground on the other side of the Hudson River, I received a response from him. We texted back-n-forth for the remainder of my walk home. When I got to my apartment, I immediately climbed into bed. I was depressed. This relationship was looking pretty bleak. Silence at dinner and an awkward kiss goodnight. Once again, maybe he just wasn’t into me.
The Principal and I continued to text over the next hour while I watched some TV. I explained to him I still had some feelings for him, however, the distance thing just wouldn’t work out for me. Apparently, I opened up a can of worms there. He really did miss me. I’m not sure why I felt the need to reach out to the Prinicpal that night. I thought I passed that chapter in the story. I think I did it for selfish reasons because I needed to feel wanted again. I knew the Principal would provide that for me. Looking back, I never should have done that.
In my mode of depression, I also responded to one of the guys who had hit me up on OKCupid. I asked him if he wanted to grab a drink sometime. I was taking my friends’ advice. I wasn’t going to put all my eggs in one basket. The guy responded, and we scheduled a date for the following night…
Follow @onegayatatimeThe Game — Hard To Get
Posted by One Gay at a Time in Gay Dating on November 29, 2011
As predicted, Monday was the day from hell. We had a huge pitch on Tuesday morning, so it was constant work until the end.
There was already no chance Smiles and I would see each other. However, we did get to chat on the phone briefly. He had to do work with his film, and I would be working until the wee hours of the morning to finalize the content for the pitch. I didn’t end up leaving my office until 1:30am.
I really wanted to see him Tuesday. I wasn’t going to be around the rest of the week, and whenever I have a long work pitch or long work trip, I look forward to decompressing with a sexy guy, even if it doesn’t involve sex. I asked him if we could do something, but he already made plans.
I was heading home Wednesday for my grandfather’s funeral. It was going to be a while before I got to see him again, and I was really disappointed. Things were really getting strained between us, at least on my end. We weren’t having sex as often as I’d like, and I was constantly on a roller-coaster of emotions. Smiles would pay a lot of attention to me and make me feel great, and then retract and shy away from me. I didn’t know how much more I could take it.
I decided I was going to play hard-to-get. I wasn’t going to text or call at all. If he still wanted to see me, he was going to have to put in the effort. I was at my emotional breaking point.
This was no easy task for me. I struggled with it. I carried my phone with me everywhere I went in case he tried to call or text, but it was silent. Part of me wondered if he thought it was a very personal family time, and he just didn’t want to bother me. But, the bigger part of me thought he had other things with which he was preoccupied.
Finally, Thursday he texted me to see how I was doing. It was progress. He was texting to check up on me, and I appreciated it. I texted him back after some time passed.
When Friday came about, he called and left a message. It was impeccable timing. I was just about to walk into the funeral parlor when my phone began ringing. After the viewing, I stepped out from the family gathering and called him back. We had a nice conversation.
The following day, I went to the funeral. Afterwards, I came home. I have awful cell service at my parents’ house. I finally managed to get signal by using the Wi-Fi. Ironically, right after I texted him, we lost power in the snow storm, so if he responded, I couldn’t read it if I tried.
I was home with no power, no internet, no phone and no TV. It had snowed about a foot outside, so we were trapped. On top of it, I was missing the Halloween festivities with my friends back in Hoboken. I wasn’t heartbroken about that, but I was disappointed. Instead, I spent the day shaking snow off trees so the branches wouldn’t break.
I was really feeling ignored overall by Smiles. The time away wasn’t a good thing for me. It was making me realize how little attention he was paying to me. I started to think about some of the other prospects I had spoken to. I could have pursued LES, but he was young and lived in an inconvenient part of town. There were a few guys who were still sending me messages on OKCupid. While I wasn’t seeking out anyone new, I maintained communication with them. I was now beginning to think about them as prospects. All I knew was I deserved better. Was I just jumping the gun? Was it still early with him? I personally thought we should have been over that hump, and if he was interested in me, he’d want to spend more time with me.
When Sunday arrived, my sister and I made our way back to Hoboken. It was a bit of an adventure with the snowfall and trees laying across the road. Once I got back to Hoboken, I hopped on Facebook. Smiles messaged me, and I learned he lost his phone. He told me about going out for Halloween and how he lost it. We made plans to grab brunch, and I made my way into the city. I didn’t forget about the lack of attention he paid me, but I tried to concentrate on the moment at hand. I was going to proceed with skeptical optimism. It was the only way I was going to keep my sanity.
Follow @onegayatatimePlaying It Cool
Posted by One Gay at a Time in Gay Dating on November 21, 2011
My weekend with Smiles was a decent one. I’m not self-destructive, nor do I get in my own way enough to think it was a failure or a bad weekend. Any time I spendt with him was progress, and it made me happy. But, I left the weekend feeling a little uneasy. I was denied twice in two days. Did he not find me attractive? Was he just thinking of me as a friend? Not knowing where I stood was eating away at me.
It’s obvious he was interested in me. But, it was his level of interest that worried me. We were in the beginnings of a budding relationship, or so I hoped. Things were supposed to be carefree and fun. The heavy stuff comes later. We should have been having sex like rabbits and dying to see each other.
I felt like I was constantly chasing after him. I got no indication he was interested in chasing me. But, maybe I wasn’t giving him the opportunity. Maybe I got so excited about him, I was constantly initiating our time together, and if given the chance, he would be asking me out on dates.
On Monday evening I texted him to see if I could spice things up with a little getaway. “Hey. What would you say to getting out of the city for a weekend?… Celebrate your birthday, just the 2 of us… Something totally low-key and relaxing like New Paltz, NY. Gorgeous this time of year too and not that far…” I thought if we hit up a bed and breakfast, we could find the time to get wrapped up in each other with no other distractions.
A big part of me thought this was a giant leap forward, and I was moving too soon, but another part of me noticed a little bit of stagnation. Things were getting a little stale. Maybe I needed to intervene to get us to that happy-go-lucky mindset.
Just as I expected, he safely replied, “Hmmm that sounds like fun, can I think on that one for a min? I’d want to be able to give you my full attention and I think with [work] this weekend, the [possibility of a new prospective work project] starting and the over two jobs with a bit of clock on them, I might not be totally present. Which wouldn’t be fair.”
I was right. Too soon, too fast. I didn’t want to cower and backtrack. I had to play it cool. “Certainly. Wasn’t exactly talking about this weekend. Was more thinking 3+ weekend out. Just wanted to throw it out on your radar,” I replied. I wasn’t lying. I was really just planning in advance.
He got my drift. I soon got a text back: “Ah. Ok. Sleep well. I’m crashing early tonight for a change.”
I decided to take some advice from friends and play a little hard to get. I stopped texting or calling. The next point of contact was going to be initiated by him. It killed me. I wanted to text so bad. I never went anywhere without my phone, waiting for him to text or call.
Tuesday went by without a word. I was in a bad place. I started having doubts about the whole thing. We were only a couple of weeks in, and he already grew tired of me. These weren’t good signs, and I started to really get down about it.
I decided, I wasn’t going to put myself back out there completely, but I was going to continue to put my ear to the ground to see what was going on out there. I started answering my messaged on OKCupid and chatting with a few guys. It was nothing crossing the line, but in a way, I was laying some groundwork if Smiles decided he was done with me.
Finally, on Wednesday, he texted me to ask me how my day was going. The exchange went back and forth a bit before simmering out. I was thrilled — Back on top. I recognized how happy I was, but I also recognized how dependent I am on others for my own happiness. This is an issue. I really need to learn to be more independent. It’s not healthy to need other people to that extent.
In our exchange, he invited me to come with him to a bar to watch a friend’s band the following night. I reminded him I had volleyball on Thursdays and couldn’t go. I really wanted to go, but another part of me was happy I had to turn him down. I have a tendency to drop everything for men I’m interested in. I needed to show I was independent as well.
Thursday went by, and we didn’t talk to each other during the day. On my way to volleyball, I texted him: “Thinkin’ bout you 🙂 .” He responded, “Good luck at your game!” It was nice he remembered I had a game. He was showing a vested interest in my life, which is always a good sign.
After volleyball, we texted a bit. He told me about how he didn’t get the project he was counting on for work. I knew it meant a lot to him, so I tried to console him as best I could. I knew he would be depressed for a few days as a result because he was really looking forward to it. I called him, and we spoke on the phone. I also took the opportunity to ask if I would get to see him Friday night.
Since he asked me to watch the band with him, I was satisfied he wanted to spend time with me, and I knew it wasn’t simply me chasing him down.
He had plans to go to a friend’s birthday party Friday night and talked about us going together as if we planned this long ago, and it was assumed I would be attending with him.
It appeared things were back on the upswing, at least emotionally for me. The question remained. Would we continue moving up, or was it only a matter of time before things started sinking again?…
Follow @onegayatatimeFriend Date
Posted by One Gay at a Time in Gay Dating on November 14, 2011
Before I met Smiles, I was chatting with a guy on OKCupid. After cruising the site, trying to find anything remotely resembling a prospective man, I managed to find a guy who was both attractive and seemed to have a great personality — at least based on his profile. He looked like he led an active lifestyle and was smiling in all of his pictures, so I sent him a message.
Surprisingly, he messaged me back shortly thereafter asking me to email him some pictures (my profile only has my torso pic). However, he added, “And just to be upfront about intentions, I’m seeing someone currently, but I’m so down to make legit guy friends. I don’t do well with the fem/gay scene so I’m always eager to meet more guys like us :)”
I wasn’t exactly thrilled, but I was also looking for friends. At the least, maybe I could get a wingman out of him. I responded, “Of course you’re seeing someone… All the good ones are!!! I can use friends just as much as I can use lovers ;)”
He seemed like a very genuine, down-to-earth guy. I was pleasantly surprised by his response. “Awww! Well you’re very cute. Why are you single?” he asked. We exchanged numbers and planned a time to meet on Thursday night immediately following work. Ironically enough, it was a night I double booked.
When my day was winding down, I texted him to confirm, but, he had to cancel. He had an impromptu second interview for a job, so I couldn’t exactly hold it against him for the last minute cancellation. Instead, I called up Sexy Eyes to see if he could grab coffee and already had plans later to meet Smiles for the first time.
I tried to reschedule with my new prospective friend, but I got no response after that. I wasn’t sure what happened exactly, but enough time passed that I lost interest. Then, out of the blue, I received a message, “Hey man, I broke up with my boyfriend 
So I’ve been in a funk. Sorry for flaking on you – I’m not usually like that, but the breakup wasn’t exactly amicable. If you want to give me a second chance, I’ve evened out and am down to chill.”
If you’ve ever read my blog, you know I’m all about second chances. However, now the roles were flipped. I was dating Smiles for a few weeks at this point, so this time I was the one looking for just friendship. For some odd reason, I didn’t make it a point to lay that out for him ahead of time, as he had done before the first time we planned to meet.
Wednesday after work, we met at Shima in the East Village, his neighborhood, for sushi. He was already waiting at the restaurant when I arrived. I sat and we immediately jumped into conversation. It was great because there was no tension or awkwardness. We jumped right in like we were old college buddies. I learned a lot about him over dinner — How he just moved to the city, what he wanted to do, what he did for fun, his family… The conversation flowed constantly. We really hit it off.
When dinner ended, we stood outside chatting a bit before he invited me back to his place to smoke and watch Archer, a show we found we shared a common love for.
The whole reason I went on this date was because my friends all encouraged me to date other people. They explained it was healthy to date a few people at the same time until you find one you really like. Things had become a but of a roller-coaster with Smiles emotionally. It went against every fiber of my being, but I decided to follow their advice. However, when push came to shove, I turned it into a friend date and couldn’t make a move. It was getting late, so after a full episode, I decided it was time for me to head home. I wanted to leave before things got awkward.
He may have thought we were on a date, but I was dating Smiles. And, as much as my friends told me I needed to be dating other people as well, I couldn’t do it. I couldn’t lead my new friend on while I had a strong interest in Smiles.
He walked me to the elevator to say goodbye. I could tell he was expecting a kiss. And, I can’t lie. I wanted to kiss him. I had a really good time, but like I said, I couldn’t lead him on like that. I knew where my true interests lay. I gave him a hug and said goodbye. I could see the disappointment in the expression on his face as he walked back into his apartment. I felt awful.
I knew I couldn’t leave things as they ended. I wanted a friendship from him, so I wanted him to know he didn’t just get rejected by me. I decided to text him to explain on my walk home.
I told him how great he is and how much I enjoyed myself with him, but I explained how I’d been dating Smiles since the night he first cancelled on me. He responded by noting, “Guess that was my loss.” We discussed it further. I realized I was wrong in not telling him my intentions going in to the date, but I didn’t know my intentions until the date was closing. I thought I could date more than one guy at a time, but it’s just not how I operate — At least not when I’d been seeing the guy for a few weeks. I could tell he wasn’t thrilled with the situation, but I had a feeling time would fix it, and we could start a great friendship.
Follow @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 @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 