Archive for August, 2011

Harvard Law’s Review

After meeting the police officer and the southern gentleman, I was on a roll. I was getting through my roster of men with ease. Monday was no different — I scheduled in a new one, “Harvard.”

I picked him up on Grindr one late night in the city. He was a very attractive lawyer who seemed pretty normal and very masculine. He went to the gym a lot, so his body was tight, and he seemed like a genuinely nice guy. We exchanged numbers shortly after we began talking on Grindr. I texted him a few times while on vacation with my family to make sure he was still thinking about me periodically while I was gone. He was another guy I thought had a lot of promise.

The night before, while waiting for the bus to meet the southern gent, I called Harvard. He picked up, and we chatted a bit. I told him about my vacation and he told me how similar his family is. He had a trip coming up in a few months and felt the same way about it that I did about mine. It was easy to talk to him. He sounded great too. No flamboyance at least. I was looking forward to meeting him in person. I thought to myself, “Maybe a phone call should be a new part of the screening process before the first date. I could eliminate a few bad apples this way.”

On the walk home from my date with the souther gent, we texted each other. He managed to slip in a comment about how much he liked my body. I certainly appreciated the compliment and threw one right back in his direction.

We scheduled a date that Monday evening at Blockheads, and outdoor Mexican restaurant. This would be my third date in two days — I was speed dating over the course of a few days. I arrived early, so I put our name down and sat to read Chelsea Handler’s My Horizontal Life until he arrived. (She’s part of what inspired me to write this blog, so I thought I should at least read her books).

When he arrived, we were seated immediately. We had a nice table for two on the rim of the crowd. A few birds flew around our feet, and he started to freak out. I get weirded out when pigeons do it, but these were tiny little birds, not the flying rats I want to punt every time I see them. Now, I’m not judging, but it was a bit excessive. He freaked out and told me how much birds skeeve him out, but I was still a little weirded out by how much it bothered him.

I started to size him up. He looked like his pictures and he filled out his polo very nicely. Great arms and a great chest. I could tell he was a regular athlete who hit up the gym. This is important to me since I am so active. I need someone who can keep up with me.

We started on the small talk. We chatted about college, family, vacation, where we grew up, what we did for fun. It was almost as if he was reading from an interview script. The conversation was alright, but it certainly wasn’t relaxed. I was a little turned off because everything he said had a slight air of superiority to it. He was trying too hard to impress me, and if there’s one thing that turns me off with people, it’s that. He even wore his pretentious college ring. He was a nice guy, but I couldn’t take the high brow attitude.

In between all this, the waiter came by to take our drink orders and then our dinner orders. Every time he came by, Harvard started flirting with him. It was obvious this guy was a ‘mo, but he wasn’t even attractive. The waiter is supposed to flirt with you for a good tip, not the other way around.

We both enjoyed our meal and continued the “interview” while we ate. He told me about his “type.” I fit the mold perfectly as far as physical looks went, but I have a feeling he was looking for a younger or more subservient guy. We would butt heads, and I think he was looking for a guy he could rule over.

When the date ended, we hugged goodbye. We didn’t even talk about follow-up. We both knew there were no fireworks there. On my walk home, I texted him, “It was nice to meet you.” He responded, “likewise.” After that, it was simply on to the next guy on the list…

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A Southern Gentleman

Before I went to OCMD, I was talking to a southern gentleman who found me on Grindr. We hit it off immediately. He seemed like a level-headed guy, and he was 35. After my last failed relationship with a 25 year-old, I decided older was better. San Francisco opened me up to the idea of dating a man of that age, and I had a good feeling about it.

The Southern Gent and I messaged each other a lot on Grindr. We also exchanged pictures. He found me exceptionally sexy, and I found him to be quite attractive. He was no super model, but he certainly took care of himself. We exchanged Facebook information. I looked through all his pictures. They were of him being crazy at a wedding, boating on a lake, safari hunting in Africa, etc. The guy had a picture of a Zebra he took down. I was impressed and swooning a bit.

We tried to figure out a good time to meet, but it always conflicted with his schedule or mine. After a while, he went completely dark. We made plans to meet one Sunday night, but when that weekend came, I got no response to the many text messages and phone calls I made. “I can only assume you lost interest already… Not sure if I did something, but I’ve sent you msgs with no response. Was excited to meet you… If I’m wrong, you know how to reach me.”

An entire week went by, and I heard no word from him. I removed him from my favorites on Grindr so I wouldn’t have to look at him every time I pulled it up. Of course, that’s when he started to message me again. He apologize emphatically for not getting back to me and blamed most of it on getting a new job. I’m definitely one for giving second chances, and I though he would be a great match for me, so I agreed to meet him when I got back from my vacation.

While in Maryland, we texted periodically. We set up a date for the Sunday evening upon my return home. He picked Pier I Cafe on the Upper West Side. I took the bus into the city and hopped in a cab the rest of the way. I made my way down to the Hudson waterfront and saw him immediately. He had a very New England country club look about him. I liked it. He didn’t look like a snob, but he looked like he appreciated the finer things in life.

We both grabbed beers and tried to find somewhere to plop down. There were no tables available, so we found a cement wall to sit on. We got to know each other slowly. We talked about our jobs, our living situations, working out, college, etc. The conversation was flowing quite easily. He is an architect, which is something that has always interested me. I found it sexy. The one hangup I had with him was he turned into a total queen every time he laughed. He was a bit flamboyant. He could have sucked all the air out of the room after every laugh had we been indoors. It was extremely off-putting. I’m sure you’re all judging me as picky at this point, but it was hard to look past. I was starting to get annoyed with these guys who claimed to be masculine. It’s my one real hangup in the gay dating world, and guys self-judge this aspect of their lives VERY poorly. Basically, I’m attracted to dudes who just so happen to be attracted to other dudes as well, not some big ‘mo.

I also started to gauge the level of chemistry between us. It wasn’t exactly at its peak either. We shared a lot in common, but I could tell the attraction wasn’t there on both sides. We both passionately talked about cooking and our specialties. It was an interesting conversation. After a while, I noticed one of my friends. He also noticed me, so on one of his trips to the bar, he swung by to say hi. I introduced him to the Southern Gent and talked to him about how things were going since his marriage in Key West.

Four rounds and one basket of calamari later, it was time to go home. I gave him a small kiss on the lips and said, “We should do this again sometime.” I didn’t have such a good feeling about our chemistry as I did before the date. I was a little disappointed, but I thought maybe I needed to give him a second chance. I would leave that up to him. If he was interested, he would followup the date with a phone call. When the call never came, I knew my suspicions were accurate. I unfriended him on Facebook so I could write about my dates without feeling guilty.

I was disappointed it didn’t work out, but that was based on an assumption I made before I even met him. I would need to not get my hopes up so high before the first date. It would be the downfall of my morale if I let the bad dates and disappointment get to me…

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Excuse Me Mr. Officer

I left OCMD at 8:00am. My sister drove me back to Hoboken, and we made great time. I also managed to ramble off a few blog entries on the drive. So much for getting caught up while on vacation, but at least I was somewhat productive. I spent so much time hooking up and working on my tan, there was little left for anything else.

When I arrived home, I unpacked, but not before turning Grindr back on. There were more than a few guys I was courting before I left for vacation, and I wanted to touch base with them. I either texted them or waited until they were in Grindr range.

One guy I wasn’t expecting to touch base with again was a local police officer. Originally when I started talking to him, it took a lot to get that information out of him. He and I sparred verbally on Grindr a few weeks earlier. He had a day off and had tossed around the idea of meeting up. When push came to shove, he wouldn’t meet up.

This time, he was a black box with no picture and he messaged me out of the blue, “Hey. It’s [X] the cop. Wanna meet up today?” Apparently, he was in the area and had some free time between errands. All I had to do was unpack and grab a few groceries, so I obliged. He wasn’t giving me any ideas as far as what we were going to do. I told him he could come over and hang at my apartment, but I was a little worried he would take that to mean hookup. I also suggested taking a walk. Finally, I suggested we grab a coffee and maybe take a walk along the waterfront. Within ten minutes, he was at my apartment. I hopped in his car and shook his hand. He was a cut little hispanic boy who wore his hat on the very top of his head. He even had the cute gay slight hispanic lisp. I found it endearing. We chatted a bit in the car until we found a parking space near Starbucks.

When we ordered our coffee, he tried to insist on paying for me, but I wouldn’t let him. There was no need for him to pay. I’m stubborn that way when it comes to money and people paying for me.

After we got our coffees, we took a stroll along the water. We talked about his precinct and what it means to be an officer of the law. He told me about his partner and their dynamic. He seemed like a really nice down-to-earth guy, but I didn’t feel a spark there. I enjoyed his company, but could not see a relationship between the two of us.

The conversation turned to family and then evolved into his ex-boyfriend. He explained how it ended and how devastated he was when it did. My heart broke for him a little. I don’t know why, but I’m a sucker for heartbroken guys — Big soft spot for them. When our walk was over, we hopped back in the car and he drove me home. He had errands to get to, and I needed to get myself ready for my date that evening and to go back to work the next day after a week away.

Based on our interaction, I didn’t think he was all that into me, but I sent the text message, “It was nice meeting you.” He responded, “It was nice meeting you too.” In my mind, that was the end.

Almost a month later he texted me, but it was completely in the context of a hookup. When I called him on this, he tried to spin it as friends with benefits. It was 11:00 on a Monday night, and he wanted me to travel to his place. He wanted sex, and nothing more. That’s fine. I’m not judging, but I also wasn’t into the hookups so much anymore. The conversation was very blunt and polite. But, if we hung out again, it would simply be as friends, or possibly from a phone call for him to come get me out of trouble…

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Whoring It Up in OCMD Pt. 2

On the way to Rehoboth, the guy from the run texted me. I explained the situation and his lack of commitment. At this point, I was in over my head with the hicks. I told him to meet us in Rehoboth. I needed to be rescued, and he eventually came to my rescue.

We arrived at the bar, The Purple Parrot, and he arrived about a half hour later. I noticed the guy who originally was talking to me on Grindr was laying claim to me. I overheard some alarming conversations that made me realize he expected some sexual action from me. “I swear to God, if he goes home with this guy after we brought him up here!” This was NOT happening. I clung to my new friend like white on rice.

The hicks went inside to do karaoke, and my new friend and I followed shortly after. We found a bachelorette party of the sweetest girls to entertain us. We all became good friends fast, which was perfect because the hicks were ready to leave. I explained I was going to stay and would meet up with them later in the night. The one who laid claim to me tried to hang back with us and even asked for a ride home, but when he couldn’t get a guarantee, he got p*ssed and left. Later in the night I received a text scolding me for never meeting up. I retorted explaining why, and my reasoning was that I was not a piece of meat for him to lay claim to.

We spent the rest of the night singing karaoke with our new bachelorette friends and taking lots of pictures. We had a blast. When it was getting late, he asked if I was ready to go home. He was a really sweet guy, and I had a good time with him. Even if I had to deal with the hicks for most of the night, I was happy to get away and got to spend some time with a new friend.

On the way home, I rubbed the back of his head while he drove, and we chatted. I wasn’t sure where this was going, but there was no way in hell I was having sex with anyone. He drove right past my condo when we got back to Ocean City and went straight to his place. When we entered, he was startled because he mom was still up. We hid in a side hallway until he could devise a plan. He told me I was going to be “Steve” his friend, and we walked past her up to the loft he was staying in.

Once we got up there, we started making out a bit. He pulled his pants down and started playing with himself. My pants were off, but I still had my boxers on. I decided to give him a hand. He finished all over his shirt and pretty much passed out. I was really hoping he’d be a gentleman and drive me home, but that wasn’t going to be the case. I would have to walk 2.5 miles home at 3:00am. I told him I needed to wake up in my own bed, got dressed and walked out.

At this point, I was very horny. Along my walk, I received a message from the guy who exchanged blowjobs a few nights before with the man I just left. I heard how hot he was, so I entertained the idea of meeting him. His roommate was home, so he convinced me to meet him in the dark alley behind his apartment building. When I got there, he was standing with his dick in his hand. He was really hot. We started making out. He undid my pants and gave me a blowjob. After some time, I returned the favor and then continued working with my hand. Shortly after, he finished all over the sidewalk. It was really hot. I thought I was going to receive the same treatment, but instead, he told me he had to get back inside before his roommate noticed he was gone. This was now two guys in one half hour that I helped with a “night-cap” who didn’t feel the need to reciprocate.

On the next leg of my journey, my mother called. I explained that “Will” had too much to drink once we got back to O.C., and I wanted to sleep in my own bed, so I agreed to hop on the bus. However, all the buses were packed to the gills, so I told her I was walking home. She stated, “You’re an adult and you can stay out as long as you like, but you need to tell us when you’re going to be out this late. Your father and I haven’t been able to sleep.”

The entertain myself for the rest of the 2 miles I had to go, I turned to Grindr. I had received another message from yet another hottie while I was hooking up in an alley. At this point I was a complete whore. Why not tack on another one? This guy was horny and looking for action. I explained where I was and where I was headed. I told him he could come pick me up, but asked where we could hookup. I suggested his car, but being a local, he convinced me it was cool if we hooked up on the beach. Just as I was getting to my street, he drove past me and turned towards the beach. I followed and met him by the sand.

We introduced ourselves and began to walk through the dunes. Just then, the garbage trucks were driving across the beach to empty all the cans. We stood and waited for them to finish before we started making out. He was a good kisser, and he quickly moved on to orally pleasing me. He was good. He was very good. Finally, someone was interested in my pleasure that night. After a while, he stood. I dropped his pants and returned the favor. I never hooked up on a beach before. It was an exciting new venture for me. After a while, I asked if he was a bottom. I explained I wasn’t going to have sex with him, but I wanted to grind on each other a bit. He agreed and turned around. I pressed my body against his and gave him a reach around. He finished all over the sand. It was my turn. I started to take over for myself while he played with my balls. It felt great. When I shot all over the sand, he said, “Wow. I’ve never seen anyone shoot like that before.” I replied, “Yea… That’s my hidden talent.”

After the two of us decorated the sand, we got dressed and started to walk back towards his car. We talked about why he was in O.C. and how he was moving to NYC in September. I told him to hit me up when he did. I was always looking for new friends to hang out with. We said goodbye with a kiss, and I walked home.

When I got home, I opened the door quietly and hopped into the sofa bed I was relegated to since my sister arrived. My mother came out to scold me one last time before dozing off. I felt like such a high school boy sneaking around to hookup and getting yelled at for breaking curfew.

The next morning, the last day at the beach, the guy I met on the run wanted to meet up and make up for not finishing me off the night before. This was a constant circus of juggling locations and sneaking around. It was becoming nearly impossible. The solution we came up with; he would pick me up in his car and we would hookup in his car somewhere. That somewhere turned out to be a parking garage, and that hookup turned into a blowjob for me. We both finished in the car by our own hands. He was heading home straight from there, while I was heading to the beach to meet my family. He dropped me off by the sand, and we said our goodbyes. He encouraged me to hit him up the next time I was home in Pa.

I was ashamed and embarrassed of my behavior on my vacation, but I got it all out of my system. I wasn’t planning to hookup at all, but even went as far as to do it three times in one night. What a whore! Once again, things needed to change, but I just told myself it was vacation. I was allowed to take a vacation from my morals for a week…

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Whoring It Up in OCMD

It was that time of year. The annual family trip to Ocean City, Maryland. Every year I both looked forward to and dreaded this vacation. While it was a week to disconnect and relax, I knew I was surely in for some excessive boredom. Don’t get me wrong, I love my family, but we’ve been going to the same place for years. I can only take so much of it before getting tired of it.

We arrived on a Sunday, and one of the first things I did was turn on Grindr. I’m addicted. I know. It’s an issue, but I also knew it would be my salvation from the boredom that would ensue. After riding in the back of the car with crap piled around me feeling like a twelve year-old, I needed to get out and do something. My parents plopped down in front of the TV, a position they would take for the next three nights as well. I wasn’t feeling so lazy. On top of that, I was already getting grief for playing on my phone while we sat and watched TV. I needed to get out.

I managed to find a nice guy on Grindr not far from where I was staying. He was from Pa, not far from where I grew up. He certainly wasn’t around the corner, but he wasn’t far either — 2.5 miles. I decided to go for a run. I could run down to his condo, say hi and turn back. It was also a good way for me to squeeze in a run as well. I told him I was going to run down there. As I got near, it appeared he was going to chicken out on me. I told him, “You’re really going to flake on a guy who just ran 2.5 miles to say hi to you!?”

Eventually, he came out to say hi. I think he had ideas in his head of us blowing each other on the beach, but I was just there to say hi. We walked around the block and talked about a few things. He was no adonis, but he was certainly a nice guy. I thought it would be nice to grab a drink with him later in the week just to chat. I wasn’t looking for anything sexual while down here on vacation. I was turning over a new leaf, remember? I said goodbye and ran back home.

The next day, a local guy found me on Grindr. He was a bit of a sweetheart. We swapped a lot of pictures, and he expressed his interest in getting naked with me. This would be very tough. I would have to plan a way to get away from the family without raising suspicion.

That’s when I created my friend “Will” from college. He was down in OC with his family. He was based on a real guy, so it wasn’t difficult to come up with material on how we knew each other, but he was not real.

Monday night, the guy I met on the run hit me up for a hookup. I told him that’s not what I was looking for. He managed to find service elsewhere. A guy invited him over, and they gave each other head. He told me how incredibly hot this guy was, but also about how he wasn’t fully comfortable with his sexuality.

In any case, “Will” and I were going for a run that Tuesday morning followed by breakfast. In reality, I was meeting this cutey for breakfast at his favorite local spot and then heading back to his house if we hit if off for some fun. Breakfast was very nice and we hit it off. I followed him to Ocean Pines, a ten minute drive from breakfast.

We went into his room and had great sex. It was just what I needed. We both really enjoyed ourselves a lot! The time came to say goodbye and head back to the family. On the drive back, I was beaming. Sex always looks good on me. Just then, N texted. He totally ruined my high. I was on this vacation to completely forget about him for a while, and he was making this nearly impossible. This was the second day in a row he texted. I called Boston to brag about my morning romp and bitch about N once again. Poor Boston.

That night, the guy from the run explained to me his boyfriend was arriving. This was the first time he brought up the fact that he had a boyfriend. My relationship wounds were still fresh. Infidelity was a BIG turnoff. He proposed we all go out, but we would have to meet “by chance.” I said, “What? So I sit at the bar looking all sad, and you two come sit next to me and chat me up? Not gonna happen.” Besides, Tuesday night was an annual tradition for my father and I to go to Hooters for wing night. He knows I am gay, which makes it even more ironic, but we always have a good time. It’s the one time of year he orders a beer when we go out. There is an element of humor added as well. My mother loves the wings, but she refuses to step foot in the fine establishment, so we order too much food and take the leftovers home to her.

By Friday, his boyfriend was back home in Pa. We made plans to grab a drink together, nothing more, but he was having a hard time committing to anything. In the meantime, another guy was hitting on me on Grindr. He was good-looking in his picture, and after talking for some time, he asked me to come with him and his 3 friends to Rehoboth for the night. I debated in my head just how risky this was. Looking back, it was a really dumb idea, and I never should have done it. But, life without risk is life unlived.

They picked me up and we went back to their condo for a few drinks before heading up to the bar. When I met all the friends, I knew I got myself into a bad situation. These guys were all hicks from right outside D.C. I wasn’t scared, but I also suspected I wasn’t going to have a good time… To be continued…

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The time came for me to start going through the roster at a better pace. I was going to meet these guys for dates and slowly widdle the list down to a quality few. I started with the guys I’d been talking to the longest and worked my way up from there. I knew their patience was probably waning, so I figured it best to start there.

One specific torso had been talking to me for weeks. He was very busy when we first started chatting with a move to a new apartment. We chatted sporadically but never seemed to nail down plans.

I messaged him on Grindr and asked if he was available to go out that week. Surprisingly, he was available that Wednesday. We made plans to grab a drink after work and take it from there. He seemed like a really nice guy and was eager to meet me. His torso shot on Grindr also proved he had a great body!

I started off that Wednesday on the wrong foot. I left the house in the morning and got half way to the PATH before I realized I forgot a belt. It was going to be a long day of me constantly pulling up my pants. Not a good day.

When work ended, I decided to walk up to the neighborhood in which we were going to meet. It was about 20 blocks and 3 avenues — nothing I wouldn’t normally walk. However, it was much more uncomfortable without a belt to keep my pants up.

We met in front of his apartment. He came down and was dressed in what I describe as spunky gay — tight striped tank top and tight straight-leg shorts. I already knew he was not going to be my type. On top of the fact that he was about 5′ 6″ to my 6′ 2″. I wasn’t going to completely write him off, but it wasn’t looking promising.

We chatted while we walked to Therapy, a bar around the corner where we could grab a drink. He had a thick hispanic accent, and at times, it was difficult to understand him. This was going to be a long date. On second thought, this was going to be the shortest date ever!

We sat upstairs at a table and ordered a round of drinks. We had NOTHING in common. We went to completely different bars, we were into very different things, and he said he doesn’t really go out much. We couldn’t have been more polar opposites. The date was very awkward and uncomfortable, and I couldn’t wait to get out of there. He asked what I had planned for later. I told him my roommates and I make dinner for each other every Wednesday, and they would be very upset with me if I skipped. This was a complete lie, but it was my out to leave after we finished the first round of drinks.

I excused myself to go to the restroom. I felt like I wasted my evening on this wet noodle of a man, so I wanted to see if I could salvage the night. I texted the next guy in my Grindr roster to see what he was up to. I couldn’t wait for a response, so I told him I’d be up for hanging out if he was around. I walked back up to the table and asked my “date” if he was ready to go. I paid the tab, and we walked down the stairs. I complained about all the old men ogling me as I descended the staircase, but he told me he was turned on by it and got off on it, reestablishing our differences.

I walked him home, and we talked about future plans. He was aware I was going to Ocean City, Maryland with my family the following week. It was an excellent out to not have to call him again. He mentioned the possibility of grabbing a movie when I returned. I told him it was a possibility, but I knew it wasn’t. I would never call or text him again. I gave him a hug and said goodbye.

As I walked to Port Authority, I pulled out my phone to see if the second Grindr guy responded. He told me he was having dinner with a friend. I offered to hang around a little while longer if he would be available later, but he suggested we do something some other night. With that, I chalked the night up to an utter failure and hopped on the bus back to Hoboken.

When I got home, I pulled up Grindr. I messaged and was messaged by some quality guys to beef up the roster. I was back to my old self. But this list was filled with guys I wanted to date, not just have sex with. I was turning over a new leaf, or so I hoped…

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The Ex’s

Still reeling from the high of a hot successful lunch date, I was pleasantly surprised that evening by the return of my belongings from N. Before he came by, I made sure I looked great. I threw on a tight tank and some gym shorts. I had been going to the gym and beach a lot and wanted to show him how good I looked. Little messed up? Ehhhhh probably… Don’t judge. We’ve all been there.

After letting him in the door, I returned to sitting on the couch. He came and sat to chat a bit. We discussed how things were going and made small talk. It was nice. We were being pleasant. I was shocked too. Not once did something catty come out of his mouth. It appeared both of us finally moved on. This was the beginning of a beautiful friendship. He couldn’t stay long. He handed me my clothing to check if he got it all. It appeared he did. I put the clothes down and he came in for a hug. It was nice. I liked hugging him. Not in a romantic way, but in a friendly way. I cared about him. I feel people are too afraid to hug these days. He even turned his head and gave me a peck on the cheek. It was very nice.

He wouldn’t be the only ex I would see that night. I had plans to see the second half of the final Harry Potter installment with Broadway. We watched the first half together right before we broke up, so I thought it would be nice if we finished the series together. He agreed.

True to my own style, I was exceptionally late. He asked me to get to the theater early to hold seats for us. It was a late showing, but it was also a new movie. The theater would be crowded. As I was running to the theater, I was texting him to calm his nerves. If we didn’t have great seats, he would wait to see it another time. This was important to him. It also bothered him because this was something I did all the time when we were dating. I have a hard time being on time for things, “but at least I’m consistent,” I joked.

I got into the theater and found us seats. He arrived shortly into the previews, and we sat back for the movie.

Earlier that day, he invited me to crash at his apartment after the movie since it ended at 1:00 in the morning. I graciously accepted since I knew how easy the commute from his apartment was. I also knew he was dating someone, so there wouldn’t be any temptation for funny business from either of us. I had no desire to revisit that past, but the thought crossed my mind wondering if he would.

On the walk home, we talked about our dating lives. I told him about all my failed dates, including the self-centered dermatologist. He updated me on his drama and the recent end of his relationship with the guy he was seeing. We were both in the same boat. It was interesting too, considering months earlier he said I wasn’t a priority in his life. I wasn’t mad about that. I was happy to see him moving on and trying to find a man. I just found it interesting.

Since the last time I spent the night in his apartment, they had done some major remodeling. It was nice to finally get to see all the hard work he put in to the place. I was happy for him. When we were both too tired to keep our eyes open any longer from talking, he set me up in his empty roommate’s bed and went to sleep.

I was just happy we could be good friends and share a movie together. We talked about going out to the bar together. Now that we spoke about seeing other men, he would be able to see me hitting on a guy at the bar. We were in a good place. It gave me hopes for N and I. I was finally making great progress with the two men who used to rule my world…

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Was that a Date?

I first downloaded Grindr as I was pushing back from the gate on my flight to San Francisco for business. Upon my return, I often played around with it at work. Early in my Grindr experience, I found a VERY sexy torso to strike up a chat with. The guy seemed very level-headed and not simply interested in hooking up. I also discovered he worked across the street from me.

But, when I asked him to hang out, he got very shy. He told me he was very picky and wasn’t that interested in meeting someone. I asked if he would grab a drink after work sometime, and he kinda let me down easy. Periodically, I messaged him after that just to say hi, but I never got much of a response. It was disappointing. Finally, I gave up.

Then one day, out of the blue, he messaged me. He asked if I had just been in Bryant Park sitting on a park bench for lunch. I was impressed and thrilled he recognized me without having met me. Ironically enough, I was on a lunch date with someone from

We chatted about the chances of him picking me out of a crowd in the city. I brought up the idea of getting a drink together. A month passed by since the last time I asked him. This time he was ready to play ball, maybe since he saw me in person? Not exactly sure. Either way, I convinced him to send me both his number and a picture of his face. At this point, I’ve had so many guys’ numbers in my phone, I needed some way to keep them straight (the first sign I was becoming a whore). My strategy was to get pictures of them to attach to their contact profile. I’m much better with faces than names.

A week later, on a whim, I sent him a text asking if he would be interested in grabbing lunch that very afternoon. I knew it was a long shot since it was such short notice, but why the hell not. Much to my surprise, he agreed. I had to run into a meeting, but would be able to meet immediately following since my work for the day was pretty much over. I told him to pick a spot. He told me he’d get right on it.

We met in the square between our offices and walked to KyoChon for some excellent wings. I had never been there before, so he explained all the ins and outs to the place. We took our food and grabbed a table upstairs.

He was great company. The conversation started immediately when I met him. The whole walk over we chatted about careers and how we got where we are today. The conversation still flowed while we ate. There were no awkward pauses or hiccups. I was very comfortable with him. He also had a great smile, something I’m coming to find is a weak spot for me. Ironically enough, he looked like Boston, had the same name as him, and he recently moved to NYC from Boston. The resemblance was a little uncanny, but I moved past it quickly.

I had a lot of respect for him. He left a very successful job at a law firm to come to NYC to find himself. He wanted a new job, but didn’t know what he wanted to do. He just knew he wasn’t going to find himself in Boston. Right now he was working in marketing, but that also wasn’t exactly what he wanted to be doing. He was still on the path to clarity.

We also talked about therapy. He was seeing a psychologist from time to time to talk through issues. He told me most people don’t realize it’s covered by most insurance companies to go for periodic sessions. He explained how it’s been a good outlet for him to get his head straight. I didn’t see him as a crazy person. I actually saw him as more sane for having such a healthy respect for it. I began to entertain the idea myself. My friends are my therapist. I have abused many of my friends in this respect and turned to writing a blog to alleviate some of that burden. Maybe a therapist was what I needed.

This was truly a quality guy. A guy I really wanted to get to know. I knew I would need to take it slow with this one. I didn’t want to come on too strong and turn him off right off the bat. We walked back towards our offices and said goodbye with a nice handshake. He turned and said, “This was good. We should definitely do it again!” I was very happy. I passed the test. Also, was this a successful “date?” It didn’t quite feel like it was a date going in, but maybe it was a lunch date by the time we were done. I was looking forward to our next.

As time passed, I didn’t push the issue of a second “date.” I also became distracted with other guys, but one day, while going through my contacts, I discovered him again. I shot him a text asking if he’d want to grab lunch again soon. He told me he was out-of-town for the week, but we would touch base when he got back the following week. Only time would tell if we’d figure it out…

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Unhappy Ending

I woke Sunday morning and decided my time with Mr. Grindr was over. N was still trying to get with him, and that was a whole lot of drama I didn’t want to get into. I was disgusted by the whole thing. It reminded me constantly of the time I cheated on N just for the sake of evening a score. It reminded me of how much less of a man I was. I didn’t need it. Plenty of other fish in the sea. I think I kept him on the roster for so long as I did because I felt guilty for dragging him into the middle of N and I.

Since no one was in town, I did what I could to clear my head. I don’t do well alone. When I’m alone, I have nothing to distract me. I star to crawl up into my own head, and I don’t like what I find. I get depressed. I know this isn’t healthy, but denial is a wonderful thing! I decided to head down to the pier in Hoboken with a few magazines and my notebook to catch up on my blogging.

Of course, I couldn’t leave the house without my matchmaker, Grindr. And once again, I found myself spending more time searching and less time writing. I managed to reconnect with a guy I had been chatting with on an earlier day. He was a sexy black man from Jersey City. I have nothing against black men, but they’re not usually my type. However, I don’t discriminate, so I convinced him to come to the pier and hang out with me.

I had been in the sun a majority of the day and was enjoying myself. I sat and people watched and read Men’s Health and Details. He showed up a few hours later. We shook hands, and he sat next to me. We started with small talk, but as the day progressed, the conversation developed more substance. We shared a great deal in common. He looked like quite the athlete as well. He had nice arms and great legs. He kept his shirt on while we sat in the sun. I found this slightly odd, but to each his own. I just wanted to see what was under the shirt.

When I couldn’t take any more of the sun, I asked if he wanted to grab a drink. I was enjoying his company a lot. He seemed like a great guy. We packed up my blanket and other things and walked to nearby Trinity to sit by the waterfront and have a few cocktails. I hadn’t had lunch, so I ordered a large salad. We both got drinks outside our usual comfort zones and shared with each other. It was nice. We were having a good time. Eventually, he ordered some food as well.

I was pleasantly surprised. This was a completely last-minute unplanned date, and it was turning out to be quite good. I was also finding myself more and more attracted to him. He had an amazingly infectious smile.

After a few round of drinks, we took a walk along the waterfront. I hit a bit of a snag in keeping the date going. It was starting to get late, so I wanted to head back to my apartment, but I also wanted him to join me. But, I had my motorcycle and only one helmet. When we arrived at my bike, I explained the predicament and invited him to come back. I would have to ride home, and walk and meet him half way to my apartment. He agreed, so I sped off.

When we got to the apartment, I opened a bottle of wine, and we went out to the balcony to relax and keep the dialogue going. When 11:00 rolled around, he was ready to head home. I invited him to stay. He knew I was no longer interested in simple hookups. I made that clear early on, so he questioned my logic. I told him, “After spending the day with you, I feel comfortable and would like you to stay.” He graciously agreed, and we started making out on the balcony. After some time passed, I grabbed his hand and brought him back to my room.

The clothes came off, and that’s when I got a bomb dropped on me. All of a sudden, I knew why the shirt stayed on at the pier. While his legs and arms were quite toned and muscular, his mid section was very flabby. It was almost as if he had lap band surgery and hadn’t completed the skin restructuring. When I grabbed for his ass, it felt like a Ziploc of water. There was absolutely no muscle definition there. He wasn’t kidding when he told me he was a mathlete in high school, and not the football player I pictured him to be.

I’m sure I’m coming across very shallow at this point, but sexual attraction is 40% of a relationship for me. This was 40% I couldn’t get over. I can be very forgiving about a lot of things on a guy, but this was tough. I had been with a guy before who had this issue, but it was very slight. I looked past it. Tonight, I could, but this guy would not be back for seconds. I liked him a lot, but I was no longer sexually attracted to him. We still fooled around, and he spent the night with me, but I couldn’t picture myself repeating the night.

In the morning, we woke and got dressed. I explained how he could get to the light rail to head home. We kissed and he invited me to hang out again. He said I could come hang at his pool sometime. I appreciated this. He really was a nice guy. I could easily see us being friends, but we certainly would not be romantically involved. I gave him a kiss goodbye, and with that, he walked out the door.

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Collection of Men

After all the drama of the week and the mindless hookup, I was ready for change. I wanted to be more present. I accumulated over 60 phone numbers of men in my phone, but had only met 9 of them at that point. I needed to fix this ratio. I needed to go on more dates and have less hookups. I also needed to find myself again.

My roommates and I decided to hit up our favorite bar. We were going to put their new connections with my favorite bartenders to good use. Once again, we had a blast, and on the way home we had a very interesting conversation.

I got into a debate with my male roommate about the perils of unprotected sex. He insisted the worry was greater for straight couples, as a baby could be the end result. I begged to differ. While bringing an unplanned child into the world can be very stressful, it certainly isn’t the end of the world. HIV can be just that if not detected and treated. It can be a life sentence just from a few minutes of pleasure. Regardless, we both agreed the perils of unprotected sex were not worth it, but we agreed to disagree about which was worse.

The conversation switched to Grindr. Both roommates couldn’t believe how easy it was for me to “meet” a guy and turn it into something more. My male roommate was jealous how easy it was to find sex, and my female roommate was jealous because of the sexy men I was talking to. I explained how both were a double-edged sword. While I had no problem finding a hot man to come over for sex, I had a very difficult time finding a man who was interested in a monogamous relationship. It is nearly impossible. I still have hope for upstanding men out there who are interested in other men, but they are becoming somewhat of a unicorn.

The next morning, while passing through the city on the way to the beach, I pulled up Grindr. Much to my surprise, my old college roommate popped up. I remembered him telling me he lived in that neighborhood, and I did know he was gay. But, I never thought about him popping up on my Grindr. When I first came out to friends, I contemplated coming out to him. He respected me enough in college to tell me early on about his homosexuality. Since I was comfortable with myself then, I thought it was only proper I told him. We talked about meeting up for drinks to catch up, but it never came to fruition.

I decided to have a little fun. I messaged him and told him I knew him. He started asking a lot of questions, and I answered them all truthfully. It was taking him a LONG time to figure out who I was. I even told him I lived with him in college. I got very specific, and he still wasn’t getting it. He started guessing names, but still wasn’t getting it. FINALLY, he figured out it was me.

We both had a good laugh. It took him from Midtown Manhattan all the way through Queens to Long Island before he figured it out. We talked about his suspicions and our interactions living together. Sophomore year we shared a room. I told him I even looked at porn with him sleeping in the bed a few feet away. He asked questions about the logistics of that, and I explained the bathroom was right next to our room, so he would have never caught me “in the act.” Also, he always slept facing the wall, which turned out to be very convenient for me! “If I only slept on my right side!” he responded.

We chatted about it some more and he joked, “I’m not gonna lie. With those big hands and your huge feet, I definitely snuck a peek here and there when you were in your boxers back then.” He was embarrassed, but I thought it was hilarious. I was also very flattered. I referred him to my blog to catch up on my gay life so far. He said he was going to read it and then realized, “This conversation is going to end up on there, isn’t it?” I told him of course it would. He suggested I leave out some parts, such as him checking me out, but I explained those were the best ones.

I was happy to reconnect with him and we chatted a bit more. We joke about the gay resident director for our living quarters. He had a crush on my roommate, while I suspect his boyfriend had a crush on me. His boyfriend is a police officer in the local city and followed me home on more than one occasion just to say hi. We had some more good laughs and agreed we need to grab a drink together soon.

I was happy to be fostering better relationships on Grindr, as opposed to the unsubstantial ones I currently had. I needed to work harder at it, but I still had hope of finding the right guy. I will have to date half the city, but in time, Prince Charming will find me…

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