Posted by One Gay at a Time in Gay Dating on August 31 , 2011 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 … Posted by One Gay at a Time in Gay Dating on August 30 , 2011 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 … Posted by One Gay at a Time in Gay Dating on August 29 , 2011 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 … Posted by One Gay at a Time in Gay Dating on August 26 , 2011 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 … Posted by One Gay at a Time in Gay Dating on August 25 , 2011 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 … Posted by One Gay at a Time in Gay Dating on August 24 , 2011 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 … Posted by One Gay at a Time in Gay Dating on August 23 , 2011 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 . 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 … Posted by One Gay at a Time in Gay Dating on August 22 , 2011 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 adam4adam . com . 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 … Posted by One Gay at a Time in Gay Dating on August 19 , 2011 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 . Posted by One Gay at a Time in Gay Dating on August 18 , 2011 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 …