Posts Tagged Martha’s Vineyard
Gym Hottie
Posted by One Gay at a Time in Gay Dating on March 14, 2012
Since my breakup with Smiles, I’ve been making greater efforts to spend more time with friends. I didn’t neglect them while I was dating him, but I certainly didn’t shower them with attention either. They’re very important to me, and I wanted to make sure they knew they were appreciated. Of course, I also just loved hanging out with them, otherwise they wouldn’t be my friends.
One of my old roommates asked me if I wanted to go out to the bar. It’d been a long time since he’d done this. It came quite out of the blue, but I was very happy for the invitation. Since we don’t live together, we get along much better. It wasn’t that we fought all the time while we lived together or anything. It’s just much simpler now. I look forward to bar nights with him.
At the same time, one of the girls who I know from my annual Martha’s Vineyard trips was planning a birthday gathering the same night a block from my office. I asked my old roommate if he minded going there for happy hour. I thought it would make things convenient so I could spend time with both. It’d been a long time since I caught up with both friends.
My old roommate and I arrived at the bar early. We made our way through the crowd at Gingerman to the bar to order some beers. I offered to pick up the first round, as I generally do. I handed him his beer and we cheersed. It was at that moment I learned it was his birthday. I had no idea until he said something. I felt like such a sh*t. He was a close friend, and I was usually up on that sort of thing. I have everyone’s birthday in my phone, so I checked to see how I missed the date. It turned out I didn’t have his birthday in there, but with more investigation, I had scheduled it a month later on the same date. I told him how bad I felt, but also added, “At least I offered to buy the round! Haha.” He laughed and quickly forgave my mistake. I thought about it for a second, and realized I was the only one meeting him for drinks. I was the one he wanted to spend his birthday with. I was touched and happy.
We stood by the door because it was the only place we could stand, drink and have a discussion. He told me his plans to go to Atlantic City that weekend for his birthday with a busload of people. I wished him luck since it sounded like such a complicated situation.
After some time, the birthday girl arrived. She came in and gave me a big hug. I introduced her to my old roommate, and we quickly caught up. She decided to make her way to the back of the bar to see if she could grab a table when the bouncer chased us away from the front door. My old roommate and I had already been back there and knew there were no tables, so I let her find out for herself after telling her that. He and I made our way to the front corner of the bar. Just as we did, a couch opened up. I texted the birthday girl to come join us. About ten minutes later, she finally did and brought the rest of her group over.
I talked with my old roommate as more and more people filtered in. It was becoming an intimate little circle. I introduced him to everyone that joined that I knew. When the evening was dragging on, I decided I was read to head home. I had to take equipment home from work, so I was going to book a car service from my office. I invited my old roommate to join me since he still lives in Hoboken as well, and he accepted. I pointed out how I bought all his drinks and provided him a ride home, proving I wasn’t a bad friend who forgot his birthday after all.
We said goodbye to the birthday girl and the rest of the group. She pulled me aside and told me how cute he was. I explained to her he wasn’t a love interest. I pointed out how she’d met him at my Christmas parties, as well as his girlfriend. She was so confused, but I realized what happened. He was guilty by association. Because he was sitting on the couch with me, and because of my status as a gay man, everyone who knew this bit of information also assumed he was gay as well.
As we walked to the car, I pointed out to him what happened. Even though there was nothing I could have done to prevent it, I apologized to him for it. He was oblivious to it, and he laughed it off.
That night, I also had to say goodbye to another ex-roommate. He was still a good friend and tennis partner. He was moving to San Francisco for work, which meant I would probably see him once a year like my other San Francisco friends. I was very sad to see another friend go. Slowly but surely, all my friends were moving away or pairing up and falling off the face of the earth. I know this is part of getting older, but that doesn’t make it any less painful.
My sister and I went to the bar where he and his friends were gathering. It was nice to get to see him since it had been so long. He’d been quite busy with his new job, but now I’d see even less of him. After I got to chat with him for a bit, I texted my other friends, D and his girlfriend and asked what they were up to. They wanted to meet up for drinks, so we decided to go to Cooper’s Union, where I know the owner and bartender.
We met them there, and the whole lot of us wasn’t charged for a single drink the entire night. He always took great care of me and my friends when he worked at my usual watering hole. Now that he branched off and opened his own bar, the attention only got better.
I had a great time with everyone that night. I got to see so many of my friends. Normally I’m too lazy to do any of these things. I always bail last minute out of selfishness, but I was trying to be better about it. It was already paying off. I had a really great time.
In the middle of all this, a gorgeous man walked into the bar. I’d seen him many times before. I’d actually seen quite a bit of him as well. He was a usual at my favorite bar, and he was a usual at my gym in the city. Apparently we both lived in Hoboken, and we both worked in the same neighborhood. I’d had a crush on him for a looonnnggg time, but had a very strong feeling he was straight. He was still gorgeous and fun to look at.
At the same time, I noticed he caught my sister’s eye as well. It’s ironic, but we have the same taste in men periodically. We both acknowledged shared interest in him, but I pointed out to her it wasn’t even worth a battle. She’d already won. There was almost no question in my mind he was straight “How do you know?” she asked. “I can just tell. But, I can also tell you he looks great with no clothes on — At least from the backside anyway,” I added. We both laughed and she continued to ogle him from afar. I did as well, but I was much more discreet about it.
When I was tired and it was time to go home, I gathered everyone to make our way home. Of course I wasn’t going to walk out without paying. I gathered cash from everyone and handed him a wad of cash before walking out the door.
I had a great night. I saw a lot of my friends in one night, I got to scope out a hottie I’ve had my eye on, and I had cheap drinks. Maybe single life was working out well for me. Maybe it was time I tried that for a while… Maybe not…
Follow @onegayatatimeRallying Friends
Posted by One Gay at a Time in Gay Dating on December 30, 2011
Every year, for the past four years, I’ve hosted an annual holiday party. Ironically, I started it with a First Annual Holiday Bash because I wanted it to become one of my holiday traditions. It would be the one time of year I gathered with my closest friends and spent time with them around the holidays to show just how much I truly appreciate their friendship.
From its first year, it’s been a big hit. An invitation one year is no guarantee of an invitation the following year. I always make sure I surround myself with the people in my life I care most about. If within the following year I fall out of touch with someone, I don’t extend an invitation.
Earlier this year, my friend reached out to me to plan weekends in December. She knows of my party and wanted to make sure I wasn’t hosting it the same night she was celebrating her birthday. We both picked dates and put it to bed.
Months later, I found out I was being evicted from my apartment since my landlord finally sold it. Our eviction date was November 30th; eleven days before the planned date of my holiday party.
This was one tradition I was not ready to relinquish, not matter what it took. Some of my friends look forward to the party a full year in advance. I make an incredible spread (not allowing anyone to bring any food of any sort), and everyone fasts for an entire day leading up to the party.
This posed a serious challenge. I would have to move into a new apartment, get it settled and cater for about forty people in ten days — A near impossible feat. However, my determination is not to be underestimated.
When I sent out my Evite, my sister immediately criticized the invitation of N. She was shocked to see I would invite him, but she also didn’t have the full story.
Apparently over the course of my short relationship with N, I mentioned my annual holiday party. As the holiday season was drawing nearer, he asked for the date of said party: “When is your holiday party so I can put it in my calendar? I’m trying to attend as many holiday parties as possible without missing one.”
Did he just invite himself to my holiday party?! I mean, he was on the maybe list, I’ll admit that. But I had no intention of inviting him in the first round of invitations.
This isn’t because I was holding a grudge over our failed relationship. It was mainly because I was disappointed in him. Considering we lived across the street from each other, I thought I’d at the very least be seeing him periodically. However, since our last discussion about our failed relationship, I hadn’t seen him once. I still had never been to his apartment considering I basically walked past it every day. He never put in an effort to be my friend following our breakup, so I no longer felt the need to attempt myself. I’d given up.
When he invited himself, I had to quickly think of the best and most dignified way to deal with the situation at hand. I started with honesty. “Oh.. Are you invited to my holiday party???” I quipped. “I’m …. just gonna go… f*ck myself…” he responded. I successfully made him feel uncomfortable, but then lightened the blow. I couldn’t do much. My hands were tied. I’m not rude enough to tell him he can’t come, but I wasn’t sure I really wanted him there either. “HAHAHA. Just giving you sh*t. Sending out the Evites today…”
When others friends learned of his attendance, they weren’t happy. I was confused by this. I didn’t think anyone would care. When we were dating, my friends loved him. Everyone approved and expressed this to me. He was a very charismatic guy to be around and played nice with all my friends. It was one of the biggest things that attracted me to him.
However, when he crushed me at the end of our relationship, everyone’s opinion of him quickly shifted.
I have to admit, I don’t know if my opinion wouldn’t have shifted so drastically. If he didn’t do anything to hurt me, I would see no need for malice toward him. I wouldn’t be his best friend, but I would certainly be civil.
This wasn’t the case with my friends. In an overwhelming show of support, they all rallied against him and attempted to convince me to retract my invitation.
I was blown away. I never experienced anything like that before from my friends. I was truly touched.
However, I would not be able to fulfill their requests. I was not capable of uninviting him. I also felt it gave him the satisfaction of thinking he still had an effect on my life. I’d completely moved on. It took a long time, and I went through a lot of turmoil to get to that point. But, I didn’t need him to know that. (Not quite sure if he’s still reading the blog…)
One friend, J, was particularly poignant in his disapproval. “I’ll crack his head open.” I told him I was going to be civil, but I wasn’t going to pay much attention to him when he arrived. “Honestly, I think its risky having him there. Especially since he is a drama oriented person.” He pointed out that N may bring up the blog in front of Smiles just to p*ss me off. “Good point… Going to have to tell him not to mention the blog,” I added. “He may leave early since no one really wants him there.”
K and some of my other friends expressed their lack of interest in interacting with him, and he didn’t really know many others. J responded, “If I have anything to do with it he will leave early.” I couldn’t believe how passionate J was getting about this. He’d never even met N. “Look I’ll be civil… but if he gets out of line you let me know.”
One of my other friends who witnessed my rebound in Martha’s Vineyard, Shorty, made the following suggestion: “You should warn him that your friends aren’t really fond of him so he doesn’t feel bombarded if people are mean to him.” “No one will be mean to him, but they’re not going to go out of their way to be nice,” I speculated. “Haha. I might be mean if I happen to end up talking to him :),” she finished.
I couldn’t believe how much my friends were rallying behind me. To be honest, I thought they all thought I blew things out of proportion when it ended. I thought they all looked at me like I was crazy for being so emotionally broken up after dating someone for a month and a half. He really did break me down a little bit, and I still feel some of the lasting effects of that relationship, as much as I would like to put it in the past and forget it. But, I thought they all thought I was being melodramatic. Apparently, they validated my sentiments.
On another level, N wanted to bring his new boyfriend. I’m sure he’s a sweet guy, but I’d never met him. I didn’t want him at my holiday party. It wasn’t the time or the place to meet him. Selfishly and childishly I also wanted the upper hand. I wanted N to see me happy with someone else, Smiles, while he didn’t have his security blanket to hold onto. I know that is very immature, but in the dating world, I am still a teenager. I’d like anyone to disagree with me they wouldn’t want to do the same thing.
So, I told him he couldn’t bring him. I explained he situation, and I think N accepted my reasoning. It was going to be an interesting night regardless. Many variables were bouncing around, and no one could predict the night, even if some of my friends wanted to start a pool of bets on how early in the night N departed…
Follow @onegayatatimeBeing Supportive
Posted by One Gay at a Time in Gay Dating on December 2, 2011
After our night galavanting around the village taking in the Halloween sights, I felt like I made a half step closer to Smiles. We hadn’t completely closed the gap, but seeing him two days in a row was a good step. We finally added sex to the mix again, and I was watching him slowly open up to me. Maybe this relationship did have potential. Maybe I just needed to be more patient.
When it comes to relationships, my major downfall is over-thinking. Luckily, I have friends. And, I have you, my faithful readers. (Oops! Did I just address the audience?) Anyway, even though I don’t have a therapist, and at times I think I need one, I have my friends.
One of the guys I swam with in college, “J,” is a dedicated reader. So much so he harasses me when I don’t post on time. You can all thank him for keeping me on schedule. We’ve been through a lot together. He was almost one of the first people I told I was gay. On my ride back from telling my parents, I met him for lunch. I planned to tell him, but at the last minute I chickened out. I was waiting until I saw him again to tell him the news, but that didn’t happen until a few months later. I am constantly reaching out to him for advice and using him as my sound board. He’s more of a help to me than he realizes.
I have a wide array of friends and different reactions I can expect from them. Some I turn to for sex advice, like my friend who knew all about my philandering on Martha’s Vineyard, even when I was trying to cover it up. Some I turn to when I’m suspicious, like A, however some of those make me unnecessarily more suspicious. Some I turn to who I know will support whatever I’m saying, like D and K. J always gives me a fair and balanced viewpoint of the situation. Boston always gives me the harsh reality dose I need sometimes. Even Broadway weighs in sometimes for advice. And nothing makes me happier than when I get advice from my readers/newly found cheerleaders.
I take everything they all say, put it through my own filter to make decisions on how to proceed. They’re all great and I appreciate them all.
Many times Smiles would tell me about conversations he had with his ex to keep him centered and sane. He was finally reaching out to me to fulfill this role, and I was thrilled!
He sent me an email asking me to call because he didn’t have my phone number. I called, and he explained how he got a replacement phone from Verizon and it was defective. I joked it was the user and not the device that was a problem. He was using a very old clamshell phone he’d used years ago.
He also told me he was in the middle of a breakdown. He had a lot of frustrations, many of which stemmed from work. Luckily, this was something he was opening up about to me recently, so I was able to give him some educated advice. He has a problem seeing things in the small picture. Too many times he looks at the big picture too soon and gets overwhelmed. I did my best to calm him down, and I think I did a fair job. Apparently, others were giving him contradictory advice to my position, but I stood my ground once again. I asked him what he really wanted. If there were no restrictions, what would make him happy. I questioned why he was settling for things just because he thought it was what he was supposed to be doing. It seemed like he was taking my advice to heart.
He told me he was going out to get ice cream instead of going for the run he planned on to exert his frustrations. As he read aloud the flavors in the cooler, I encouraged him to pick something indulgent and go home and have at it. He was stressing a lot and needed to take the time to relax. Sometimes I wonder if he forgets to step back and have fun.
When he got back to his apartment, he was feeling better and was ready to dive into his pint of Ben and Jerry’s. He thanked me for the pep talk and said goodnight.
I went back to watching TV on the couch, but I had a smile on my face. He turned to me in a time of need. I finally felt needed and appreciated. I wanted to be more integrated into his life, and this was a step in that direction. I sat there thrilled a the new development.
Was this the foundation of a relationship?
Follow @onegayatatimeFabricated Frustrations
Posted by One Gay at a Time in Gay Dating on November 4, 2011
As things were progressing with Smiles, I started to feel guilty about The Principal. I really liked him, but I didn’t want to string him along. I needed to do some damage control.
I legitimately enjoyed talking to him and found him to be a great guy. If he lived closer, I’m sure a relationship would have developed, but living six hours away prevented all that. The time came to protect his feelings. Through our discussions, I knew he was falling for me harder by the minute. I needed to cut things off before we got any deeper, even if that meant hurting him a little now. I needed to find a way to do this without hurting his feelings.
I decided to approach it by telling him the distance thing was getting to me. I was going to blame it on that so he didn’t feel responsible for my wanting to morph the relationship into a simple friendship. This is how the conversation went down:
Me: “So, I told you I would always be honest with you on things, and I’m starting to have my doubts about all this.”
P: “Okay. What’s the mater? Figured you were giving up on me.”
Me: “I just haven’t seen this going anywhere… I can deal with the distance as long as there is progress, and I haven’t seen that. I’m worried if it’s been this tough so far to get things off the ground, it’s only going to get tougher.”
P: “We are not in a relationship. This isn’t preventing you from doing anything. So what’s the harm? Next, what’s been tough lately? What happened over the past 3-4 days?”
Me: “I think you are a great guy, and I like you a lot. But, I’m having doubts this is a good idea if feelings are getting involved. What changed is I had a hard time both remembering to text or call and to find the time to do so. And, I feel bad about that! However, I don’t hear my phone ringing all that often to be honest either.”
P: “And, this came about because? Have I done something recently?”
Me: “You’ve done nothing wrong.”
P: “K. You don’t need to feel bad.”
Me: “I’m just being honest.”
P: “I haven’t called in the past 2 days because I was waiting to see if you’d put in some effort.”
Me: “I mean in general.”
P: “So, you feel I don’t call or contact a lot first?”
Me: “You text me, but you know how I feel about that. I can’t think of this as not a relationship. I’m not capable of that based on how we talk to each other. And by tying myself up in this relationship, I don’t feel I’m opening myself up to something else, and I just don’t know if this is enough for me. Does that make sense?”
P: “It does. Why did you feel bad this weekend? You weren’t thinking of me? It’s okay. Um. You’d date a guy if he came along right?”
Me: “Which goes to say, it’s not that I don’t want to talk to you anymore. It’s just the tone and frequency that may change.”
P: “I mean first you have to be interested in someone? Then you can worry about that. No? You should worry about not being able to open up to a guy when you see someone who interests you. What can I do to have you continue to be close? My ‘babe?’ LOL.”
Me: “And, how is this fair to you? I string you along until I find another guy? That’s not right!”
P: “I know the risk I’m taking. You find another guy, I back off and let you be happy.”
Me: “I know. But I don’t play like that. The emotions that build up until I meet someone else.”
P: “Obviously sounds like you just don’t like me that much.”
Me: “I like you plenty. I just don’t like the situation. And, I don’t want to hurt.”
P: “And, then you meet someone. If we meet before then, we could discuss different terms.”
Me: “This isn’t easy, but I’m trying to make the mature decision. I thought it would go down differently than it has. I thought after a month I’d have seen you already.”
P: “I’m shocked by this.”
Me: “I thought we’d be making this work long distance, when really it’s just been ‘how’s your day’ text messages and calls.”
P: “I know you want more in-depth talks.”
Me: “We had a fight about this… I told you I wanted more. I haven’t seen more since then.”
P: “How else is making this work long distance? More talks? I have a feeling that still won’t be enough.”
Me: “Exactly. I thought by now we’d be planning a second visit. We haven’t had a first.”
P: “You haven’t been home at night. Been doing every sport in the world.”
Me: “I’m not pointing fingers in blame! By any means. I take responsibility as well. I lead a very active lifestyle.”
P: “Yup.”
Me: “I just need more if I’m in a relationship, and if I’m not getting that, it’s more of a friendship. Just redefining us. Not eliminating us.”
P: “Well. Not hearing ‘babe’ or having that closeness… Seems more like eliminating.”
Me: “I’m sorry you feel that way.”
P: “Just unhappy about this obviously. I can try to have more intimate talks and move us forward.”
Me: “I think we need to discuss this more, but I have a busy afternoon until this evening…”
P: “I like you. I feel emotionally connected to you. Of course you do. “
Me: “Can I call you later? And that snide comment is exactly why I feel this conversation needs to happen.”
P: “Yet, I get the blame for no contact. I might be with friends later.”
Me: “I’m not going to fight with you about this, so please drop the combative attitude.”
P: “I’d stop anything for a guy who will do the same for me. Babe. You made up your mind right?”
Me: “No. I want to talk to you about this, but I have work to do.”
P: “So you want to talk more to tell me how you want less contact and just a friendship?”
Me: “You are impossible. I want to discuss how we can proceed from here. Please be an adult about this.”
P: “I am if you are saying you are open to developing our closeness. Great. If you are going to continue to explain our new status, I get your thoughts. I’m not mad. Have a good afternoon. I get that you want the tone and frequency to change. I’ve missed you and care about you and think you’re an incredible person.”
With that, the texting conversation ended for the afternoon. I wanted to pick up the phone and talk to him like adults, but every time I called, he ignored me. He would go right back to texting me, but would not discuss this over the phone. I don’t like having conversations like this over text. You can’t hear someone’s tone in a text. Later that night we chatted some more:
P: “In bed thinking of you. Very unhappy about this situation.”
Me: “I don’t know how to fix this. I’m sorry. I know I need more in a relationship, but I’m also trying to take your feelings into consideration.”
P: “You need more, so go find more… I’m very frustrated.”
Me: “What are you frustrated about?”
P: “That you want to just quit and be friends.”
Me: “I don’t want things to get messy. I don’t want to hurt you. How are you going to feel when I say, ‘I met someone?’ “
P: “I’m sensing you just lost interest. I’m a big boy. You meet someone and then I’ll get put aside. You don’t like me. Then there’s not much I can do with that.”
Me: “Okay. The truth is, I did meet someone.”
P: “K. That you should have said. So much for always being honest. So what’s with the I don’t know how to fix this?”
Me: “I thought it would make things easier if I asked you to just be friends, but if that means you think I don’t like you, then I feel the need to come clean… Cause I do like you.”
P: “Okay. I wish you luck. You’re a great guy.”
Me: “I want to keep you as a friend. That’s why I’m treating treading so delicately. Are you okay?”
P: “We can be friends, but I need space… I’m fine. Not happy about it, but what can I do?”
Me: “The last thing I wanted to do was hurt you! You’re an amazing guy!”
P: “We are going to change our relationship, and that’s not going to happen soon. If you’re ever single and want to explore, definitely contact me. If I’m single, who knows…”
Me: “Okay. I’ll give you space. When you feel comfortable, please reach out to me again!”
I didn’t feel I got the closure I needed with him. I could tell he wasn’t happy and a little heart-broken. I didn’t know what to do, but I knew if I kept up the charade, it would only get worse down the road. I think I did the right thing. I did what needed to be done. Now it was a matter of time and healing before he would reach out to me again.
Follow @onegayatatimeSkype with Massachusetts Mainlander
Posted by One Gay at a Time in Gay Dating on October 21, 2011
Since I left the island of Martha’s Vineyard, not a day went by I didn’t talk to the Massachusetts Mainlander.
Every day, we either texted or talked on the phone. One of us would text the other to say good morning, and throughout the day, we’d call each other to talk on the phone.
I liked chatting with him. I wasn’t sure where things would go between us. We live six hours apart. I tried the long-distance relationship thing with San Francisco, and we could have made it work — He just wasn’t completely compatible with me. I always have my doubts about long-distance relationships, especially with me, but I was willing to give this a shot if nothing else was coming my way. I’m the kind of guy who needs someone present. I like coming home to a man or going to a movie or laying together on the couch. Distance is not something I welcome with open arms.
I never met The Principal, so that threw in a whole other element. Face-time was important to me. If I couldn’t be with him physically, I needed the next best thing – Skype.
It wasn’t easy to convince him to come on Skype. It took a lot of arm twisting. When we started, I could tell he was very self-conscious. He was constantly adjusting and fixing himself. He wouldn’t even speak on Skype. He insisted on typing and blamed it on his roommate being home. I kept telling him to relax. “It’s just me,” I told him. Afterall, we developed quite a bond over the phone over the past couple weeks.
Our conversation was pretty standard (abridged of course), but would need to build to grow into a full relationship:
P: I’m all warm and horny now. LOL
Me: Haha. Oh really?
P: Def. LOL It’s this really cute guy in front of me.
Me: You look so snuggly right now. Like I could nestle in the armpit and watch TV with you. The real thing would be so much better, but this will do for now 😉
P: Pizza with roomie coming soon.
Me: I’m making pizza tonight from scratch.
P: When you cooking for me?
Me: As soon as you come stay with me for a weekend 🙂
P: All weekend?
Me: Yes. You come straight from work Friday and leave Sunday afternoon, so you can get home and relax before work on Monday. We can snuggle all weekend. Maybe I’ll show you New York for 5 min, and then, we’ll come right back here.
P: LOL You’ll hate me after that weekend.
Me: Why do you say that? You know it’s not true!
P: Too much of me. LOL
Me: No such thing! What… You’d come down for the day!? THAT’S DEF NOT ENOUGH TIME TO SPEND WITH YOU!
We were both laying it on pretty thick. Maybe I was getting a little carried away, but I really did like him. He seemed like a great guy. Had he lived in the same state, I’m sure we’d have been on many dates by then.
Me: See my room?
P: I dont konw what to do with you!
Me: My big bed…
P: It looks really comfortable.
Me: There’s a whole side with your name on it.
P: You are so awesome!
Me: You are too!!
P: Think about you alot… Potential of where to take this…. Never thought it would come to this level you know?
Me: I know. You’re quite the skeptic.
P: Well, I mean it was Grindr.
Me: Grindr is just the medium. The vessel.
P: I know but… Just mesh with you.
Me: You get out of it what you put into it. Doesn’t matter where you meet someone. Still think you should have hopped on the ferry and had dinner and drinks with me.
P: That time is done though.
Me: I know. I konw. So, now you should hop in the car. and have dinner with me. 🙂
P: That’s a long drive for dinner. LOL
Me: Dinner doesn’t end at the restaurant.
I also really enjoyed flirting with him. He responded very well to it, and I could tell he was very attracted to me. I was curious if he talked to anyone else about me. I didn’t broadcast to my friends I was talking to someone in upstate Massachusettes, but I did discuss it with my roommate.
Me: Have you mentioned me to ur roommate at all? Told my roommate about you. She comes home from work… “How’s Steve?”
P: I haven’t talked to anyone about you.
P: Def. takes it to another level — Seeing you and conversation. I want to feel close to you, smell you, nuzzle… I’ve only been with 3-4 guys (full intercourse), and I def def want to be connected with you bad.
Me: I love the way you describe it — Makes it romantic, sensual, passionate. I want to toss you down on my bed and treat you right!
P: I want to be tossed. 😉
The pillow talk died down a bit, and we talked more about relationship desires.
P: I want to rub you.
Me: A shoulder rub from my sexy man when I get home from work, and he tells me all about his day.
P: And, the back of your head.
Then the conversation took a turn I wasn’t thrilled with.
P: You need a great guy close to you.
Me: First, we figure out us.
P: You’re incredible.
Me: Then, we figure out the distance. Can’t let that be an obstacle.
P: Not what I meant.
Me: I need you close to me.
P: You should be dating someone close to you.
Me: STOP TRYING TO PUSH ME AWAY!
P: I want you to be happy.
Me: I really dont like when you do this!
P: K. I’ll stop.
Me: Good.
After that short detour, we got back on track:
P: Obviously I want you for me. I’ve been wrecked by you. Not even into talking to guys right now. You fulfill so much already. OMG — You are killing me. We touch base all day every day…
Me: I want you to be my man!
P: Care about you… This.
Me: You’re adorable. I just want to hug you all night.
P: Def could get lost in those arms.
Me: This could all be yours!!! For the low low price of a car ride 😛 I don’t want to pressure you though.
P: It would be the prize of the century.
P: I just feel really good with you.
Me: And, I with you.
P: And, the sexual is like beyond crazy. LOL I can’t imagine the chemistry.
Me: We can do this again soon. Now that you enjoy it.
P: K… I really like you! 😉 Bye.
The Principal was a really great guy. I really liked him. He didn’t know it, but he was also providing me an invaluable service. He was distracting me from Smiles. I have a tendency to dive in full force, even when I barely know a guy. The Principal was giving me an outlet for this so I didn’t scare off Smiles. I wasn’t exactly using him. I did enjoy conversing with him, and I really did think he was a great guy. But, only time would tell if this relationship had two legs to stand on…
Principal’s Office
Posted by One Gay at a Time in Gay Dating on October 4, 2011
Starting the final Friday of my vacation, I began talking to a very interesting man on the mainland of Massachusetts. Right off the bat we clicked. Of course, I found him on Grindr, but that doesn’t mean he isn’t a man of quality.
I tried my hardest to convince him to visit me. I suggested we grab a drink and/or dinner. We went back-and-forth on the issue, and of course, I ultimately lost. No matter how hard I tried, he would not get on a ferry. Even after offering my bed following his question of where he would sleep, there was no convincing him. I went as far as to pull a shirtless picrture out of my arsenal. No dice.
But that didn’t deter me. We spoke every day of the rest of my trip. I enjoyed his messages. I enjoyed the cat-and-mouse game we played. When the time came to drive home, I turned to him to entertain me for the long car ride. We started messaging each other the second I hopped on that ferry. Had I been in charge of my own transportation, I would have made a detour on the way home, but that wasn’t an option for me.
Instead we took the oppotunity to get to know each other over five-and-a-half hours. I learned about his job as an elementary school principal. I enjoyed picturing him with a myriad of children circling around him. I remembered how much respect I had for my principal growing up. It was fun to picture the little tykes looking up to him. I learned he swam in high school and coached a team as well, but he had to give it up when he left the classroom for the principal’s office.
When we stopped at a gas station, I surprised him by calling for the first time. It was great to hear his voice. He never expected me to pick up the phone and call, but after talking to him for three days, I thought it was time to speak to him instead of just texting. The conversation was short, but it was special.
Once we got back on the road, it was back to texting. Periodically, I would switch back to some of the other guys on Grindr, but I didn’t have much interest in them. They lived in Rhode Island, Connecticut, etc. It was crazy enough I was trying to continue the conversation with someone in northern Massachusetts.
However, I learned one thing when I was working things out with San Francisco from across the U.S. You can find ways to make a long distance relationship work, but certain understandings need to be met. Both parties need to be willing to put in great effort to make it work, and an end game needs to be discussed at some point.
My mainlander continued to point out how ridiculous it was for us to be talking. He was very skeptical of the whole thing. I tried my hardest to get him to open up. I told him, “I’m not thinking about that bridge until I come to it. Right now I’m just enjoying chatting with you. Does it make sense to do this? No. But could it be something special? Only time would tell. But, it’s sure to fail if you don’t give it a chance to even begin.”
With every word, I found myself falling for what I pictured this man to be. I proceeded with caution, but I was also diving in full force to explore the possibilities of where our conversation could go.
When I arrived home, the conversation ended for the day. I was preoccupied with other men, but that doesn’t mean the conversation between us ended at that moment. I liked everything I was discovering thus far, but there was much more digging to be done…
Follow @onegayatatimePrince Charming Pt 2
Posted by One Gay at a Time in Gay Dating on October 3, 2011
Ever since my first date with Prince Charming, I have been trying to see him again. With the exception of being unavailable often because of his job as a flight attendant (soon to be pilot), he was everything I was looking for in a man. I thought about him often, but tried to curb my excitement for fear I would find myself disappointed.
We spoke on the phone for an extended period of time while I was in Martha’s Vineyard to try to plan a time we could get together. It was nice to get to hear the sound of his voice again. He told me his upcoming schedule and planned to get together the Wednesday after my return from vacation. He would be coming off a long working weekend in Scottland Tuesday evening.
When Tuesday rolled around, I started to become worried about the potential for Wednesday. I was back to work and knew the full scope of work laid out for the week. We had a pitch that Friday that would lead to me traveling to Memphis Thursday afternoon. I knew my Wednesday night was going to be stolen by work. Tuesday when he landed, he sent me a text message. I near lept for joy. I was thrilled he reached out to me. I was on his mind. I texted him back on my walk home from work. It was pouring outside, but I still had a smile on my face.
I took the opportunity to warn him I possibly would be unable to meet Wednesday. I asked him what the chances were I could see him that night instead. I knew he was tired from the long trans-Atlantic flight, so I proposed ordering take-out and a movie on the couch, even though I owed him a home-cooked meal from scratch. It was already 7:00, and I had no time to plan out and cook a meal to the extent I would need to impress him after his spectacular creation for me.
Surprisingly, he bit. Once I explained both my roommates would be out of the apartment, he agreed to come over. I was shocked at how little convincing he needed after telling me how exhausting that flight is. He said he would have to shower and get ready to come by. He was moving at a snail’s pace after waking up from a nap and apologized for such. He asked for my understanding. I told him to take whatever time he needed, as long as it meant he was coming over. I was literally blissfully walking through puddles as I texted back to him. I didn’t care what was going on around me. I had a smile from ear to ear, and two very wet shoes.
When I got home, I cleaned my room and showered. He asked me to find a good Italian restaurant to order from. I called my Italian ex-roommate to ask which one he preferred since I respected his taste in Italian cuisine. I set the menu on the counter and waited for him to call. I instructed him to pull up in front of my apartment, and I would hop in the car to help him find a parking space. He already resented Hoboken and its lack of parking. Anything I could do to offset that would work in my favor.
He drove around for quite a while before finally calling me. It was a downpour outside, so parking was even more at a premium. He pulled up and I hopped in the car. I leaned across the car and gave him a kiss. We drove around for twenty minutes without finding a single space that wasn’t flooded out. He said the only other option was to go to his place, but he would have to drive me home late at night because his roommate (the one that isn’t his ex) was coming home at 5:00am. I didn’t question it at the time, but a huge red flag went off in my head. Why did it matter if his roommate came home? It had to have something to do with living with his ex. When he brought me over to his apartment the fist time, no one else was home. He was hiding something, even if he told me in full disclosure he lived with his exboyfriend who he was separated from. At that point, I suggested he drive home and take a cab to my apartment, but he was ready to give up.
He asked me to give him credit for the effort, but I wasn’t satiated. I wanted to spend time with him. He made me happy. The parking situation was ruining my night. It had nothing to do with not getting sex. I just wanted to spend time getting to know him.
He drove back to my apartment and dropped me off. I gave him a few kisses and went on my way. I walked back into the apartment like a defeated soldier. We agreed to try for the following evening, but I had very low expectations for that. It was late, and I was starving. I found some frozen food in the freezer that was easy to heat up, and I sat on the couch for the remainder of the evening alone with the TV remote.
The following evening, I found out I would not be at work that late. I texted him immediately, only to find he was unable to come over. He had an early training flight the next morning. We agreed to shoot for the following Tuesday to meet up again. From that moment on, I resolved myself to not get my hopes up. The new discovery about the sneaking around his roommates did not bode well for progress between us.
The following Monday, I sent him a text asking if I would get to see him. After getting no response, on Tuesday I followed up with a phone call but still didn’t receive a response. When Friday came along, and he signed on Grindr, I messaged him to ask if he was avoiding me. I also sent a text, should he not get my Grindr message. I wasn’t going to stalk him, but I was shocked he would treat me like this after telling me how much he enjoyed my company. He finally responded, “I am going through some things with my ex, and I don’t want to drag anyone into the middle of it.” I immediately replied, “I have to respect that, but I have to tell you, I’m very disappointed.” He texted back, “I understand and apologize.” That wasn’t an acceptable apology for ignoring me. I thought he was different and would treat me with respect. If he told me that instead of avoiding me, I would have had to accept it and move on. It’s just the games I don’t appreciate.
Who knows if it really was his ex or if he just lost interest in me. I will never know. I followed up with a text saying, “That doesn’t mean we can’t grab a friendly drink sometime at the bar. Don’t be a stranger.” I still needed friends as much as I needed a lover. I was willing to accept that level with him since I thought he was such a good guy. However, he must feel differently. I haven’t heard from him since…
Follow @onegayatatimeBooty Call
Posted by One Gay at a Time in Gay Dating on September 29, 2011
On Labor Day, we began our journey home early in the morning. It was a fun week in Martha’s Vineyard. It wasn’t quite the same as other years. Outside my dalliances, the week seemed very tame. I wondered if it was because some of the group are now paired up, or if it was because we are getting older. Either way it was a great way to end the summer, even if I’m not exactly proud of how I behaved this summer.
I spent the five and a half hour ride in the back of the car. While I was on the island I found a guy on Grindr who lives on the mainland. I tried my hardest to get him to come visit for dinner/drinks/more, but no bites. I talked to him the entire ride home, but that’s another post for another day.
I knew I’d arrive home mid-afternoon. I didn’t want to waste the day unpacking and lounging in front of the TV, so I tried to lay some groundwork for an evening date with some of the candidates still on the roster. When none of them replied, I was quite disappointed — And, horny. After chatting and exchanging pictures with my Massachusetts mainlander and other random Grindr men I encountered on the road home, I was in the mood for some action. I didn’t want to pull in another random from Grindr or adam4adam.com. I was trying to curb sex with strangers. I did however have two friends with benefits still in my back pocket. They were itching to hop in the sack with me as much, if not more than I was with them. They both messaged me numerous times while I was in Martha’s Vineyard to inquire about my return home.
I called up Closet Guy and told him to come over. He jumped at the opportunity, but needed to run home and shower before he could come over. And, just my luck, one of the guys on my roster took that moment to respond about meeting up that evening. He had been on the roster for MONTHS. He was one of the first guys I talked to, and we had been trying to meet up ever since. I wasn’t going to turn down the opportunity to finally meet up, but I also had to deal with Closet. So I did what any horny, selfish guy would do — I scheduled both back-to-back. I told Closet to hurry because I needed to go into the city to meet up with a coworker to discuss everything I missed over the week before heading back the next morning. It was perfect. He would come over, have sex and leave without any of the post sex chatter.
(Warning: The following may be too graphic for some) When he arrived, I brought him straight to my bedroom. He stripped, and I threw him down on the bed. We made out like we hadn’t seen each other in months. Hands all over each other. It wasn’t long before he was begging for me to be inside him. He hopped on top of me and went to town. It was just what I needed after a long car ride. Shortly after, I rolled him over and we tried a few other positions, ending with him on his back. That’s when things got slightly messy. It’s always unfortunate when that happens, but it happens. It’s the nature of the beast. It’s quite a mood killer, but I always try to be dignified about it. I’m sure it was a learning experience for him, as I was the only one to penetrate him. I asked him if he wanted to move things to the shower and conveniently laid the hand towel I had at my bedside over the spot on my comforter as to not draw attention and embarrass him further.
Once in the shower, we lathered up and continued the fun until we were both fully satisfied. It actually worked out quite well because I love shower sex, and I needed to shower before heading into the city to meet the long-haired hunk I texted earlier. It was both fun and a time saver.
We toweled off and got dressed. I kissed him goodbye at the door and continued to get ready for my date. I thought things would change when I arrived home from vacation. I thought I would get back to my old self where I could only have sex with someone I truly had feelings for, but I was wrong…
Follow @onegayatatimeSex On The Beach
Posted by One Gay at a Time in Gay Dating on September 28, 2011
Friday had come and gone on the island, and I behaved myself. I was trying to enjoy my time with my friends and stop thinking about finding a guy to hang out with, hookup or not. But, when Saturday rolled around and most of my friends were all coupled up, I started feeling lonely once again.
We went to a bar in Oak Bluff, Offshore Ale Company, to pregame for a night on the town. We ordered plates of french fries and tried some of the many beers they offered on tap. Everyone was well on their to a drunk night.
Throughout the night, I texted the Russian and tried to get him to come out to the bar. He wasn’t interested. However, he was quite horny and was looking to meet up with me. He proposed we hit up a remote stretch of beach between Oak Bluff and Vineyard Haven. He told me he’d drive over and pick me up in twenty minutes. I had patchy service everywhere on the island (Thanks for nothing T-Mobile!), so I was worried he wasn’t going to be able to reach me. Ironically, that night at the bar, I had exceptional service, but almost forty minutes passed by with no word from him. I texted, but I received no response.
I figured he was either running behind or something came up, so I contined to hang out with my friends. Ironically, I ran into my college teammate’s best friend whom I’ve drank with many times in Hoboken. We chatted a bit before he needed to leave, and then I made my way back to the rest of the gang.
I excused myself to go outside to call the Russian and see what was up. I told everyone I’d be back in a minute after I made a phone call. When I got outside, I saw him standing by his car. He apologized for not getting back to me because he forgot his phone at home. I hopped in his car, and we left for the beach. I texted one of my friends to explain I wasn’t coming back in the bar, but I would join up with them later in the night.
We pulled off the road into a small parking lot by the beach. Just as we were walking down to the sand, another car pulled up. We figured we’d need to walk a bit to get out of site of the new arrivals. It didn’t help the moon was bright that night. (Warning: The following may be too graphic for some). When we found a spot, we started to make out. He unbuckled my belt and unzipped my pants. He got down on his knees in the sand and went to town. He felt amazing. Already, this was much better than the ginger and the construction site. All attention was coming to me, and I was basking in it. He took off his sweatshirt and laid it on the ground and laid down on his back on top of it. I laid on top of him. By now, both our shirts were off and our pants were around our ankles.
We agreed there would be no penetration, but we were going to have our fun in other ways. And, boy did we. We tried many positions and permutations, trying to avoid getting sandy at all times. After we finished decorating the sand, we got dressed carefully and walked back to the car. The last thing I wanted was to spend the rest of the night at the bar with sand in my clothes and boxers. We sat on the hood of the car and shared a cigarette. When it was finished, we hopped in, and he drove me back to town where my friends were drinking and dancing at the bar.
I arrived too late and was not granted access, however, this worked out well because some friends were heading home anyway. I joined them to head home for some late-night mac n’ cheese.
It was nice to have a friend with benefits on the island. He lived on the island year-round and makes his living in various ways, one of which is photography. This would be the last action I got on my vacation, but that didn’t mean the conversation ended there.
Since leaving Martha’s Vineyard, I became Facebook friends with the Russian. The Boston guy with the girlfriend has made it a point to text and email me the dates he is coming to New York City. The ginger photojournalist has texted me once to reiterate the good time he had and to ask how the rest of my vacation was going once he arrived back in D.C. Overall, it was a nice ego boost. Apparently I’m that good and hot enough they felt the need to followup.
Most likely, I will never see any of them again, but I take with me some fun memories and new experiences. Just as my vacation was ending, my priorities began to shift. Sex was starting to severely lose its mystique. It tends to do that when you have meaningless sex. I needed a change and this was a good transition point. When I got home, things were going to be different — Or at least that was the plan…
Follow @onegayatatimeCan I See Your Press Credentials?
Posted by One Gay at a Time in Gay Dating on September 26, 2011
That time of year finally arrived — The end of summer. It’s always both a sad time and a happy time for me. I am a sun worshiper. I love the beach, and I love a good tan. It means the days get shorter, and the nights get longer, which isn’t necessary a bad thing when you have someone to share those nights with. Of course if you’ve read this blog at all, you know I don’t have that someone. However, it is a happy time for me because it means the annual Martha’s Vineyard trip many of my friends and I take has arrived. We always have a blast, and it’s one of the best crews I’ve ever traveled with. Everyone is mature and responsible, yet they still know how to have fun.
Since things ended with N, I kinda went on a whoring rampage. My time in OCMD was nothing short of scandalous. But, I was having fun. And, why shouldn’t I? I’m a single 27 year-old who is still finding himself in this new gay world. While everyone was having sex in high school and college, I was a good boy. I had my share of awkward hookups with women, but nothing successful enough to blossom into a relationship and rarely something worth revisiting again. Plus, the only way I would get better at sex was practice. So practice away I shall.
We hopped on the ferry to the island, and I fired up Grindr. I was beginning this trip with five other straight friends and ending it with ten. I knew I would crave some stimulation from other like-minded gentleman. Many of my friends were in relationships, some of which were tagging along on the vacation. I didn’t want to always be the third wheel. I made an effort to find someone to maybe sneak off on my own with.
Of course I found a few attractive men right off the bat, but pickings were actually quite slim. Many of the attractive ones happened to be on the mainland. One guy in particular messaged me. He was on the Vineyard covering the President’s vacation and had stayed on longer to cover Hurricane Irene as a photojournalist for CNN. He was staying in Vineyard Haven, where we were pulling into port around 9:00am. He could see my ferry coming in to port from his hotel window. He suggested I come by. I was definitely intrigued since he appeared to be quite an attractive man — Fit and handsome. I was also intrigued because originally he told me he was a CNN journalist in the President’s press corp. I thought it would make for an interesting story for the blog (This thing can be such a bad influence on my decision-making process sometimes!). He was a bit older, but I was on vacation, so my standards could also take a vacation. I explained to him I was just arriving on the island and would need to get settled in. Coming over for a quickie was not a solid option. That didn’t deter him. He certainly was persistent. He was waiting for a ferry, but was unsure which one he would get on due to the cancellations from the hurricane.
We arrived at our house and began unloading the car. We settled in and unpacked. I was originally under the impression we’d be heading directly to the beach, but everyone seemed to be lounging about. I inquired if I would have time to go for a run before we went anywhere. Everyone agreed they weren’t heading anywhere fast. I wasn’t really all that into meeting this guy, but at this point, there was no reason why I couldn’t. Am I proud of this? HELL NO! I was stupid and saw it as a challenge. So, I told the guy I was on my way.
In my haste, I left for the run shirtless. I hate running in a soaking wet t-shirt, so I left it behind. I wasn’t thinking ahead to the part where I would be walking into a hotel without a shirt on soaking wet from a run.
I texted him the whole way, almost getting hit by a car twice. He told me his room number and planned to leave the door ajar. He would be waiting for me in the bed. I was not really comfortable with this. I really felt like a gigolo, only I wasn’t getting paid. I explained my need for a towel when I arrived to help with the sweat from the 1.5 mile run, so he left one hanging on the door knob for me.
When I arrived, I walked right past the front desk straight to the elevator. When I go to the door, I entered the room. He was waiting on the bed for me. I removed my shoes and began to take off my shorts. He pulled me in, and we started to make out. I didn’t realize from his pictures he was quite the redhead. His entire body was freckles. He was my first ginger. Without getting into the details, we had our fun. SAFE fun. When all was said and done, I picked up the towel again and cleaned up as best I could. He couldn’t stop telling me how sexy I was and how great my body was. I don’t embarrass easily, but he was certainly making me start to blush. He told me if he didn’t get on the ferry that night, he would be calling upon me to go on another morning run the following day. I knew this wasn’t going to happen, but I humored him anyway. We exchanged a kiss, and I was back off on my run home.
Of course, the second I left for my run, everyone back at the house began speculating on my reason for leaving. I knew this was going to happen, and I could tell the second I walked back into the yard they had been discussing this. One my friends, a very loyal reader, immediately grilled me on how my run was. I saw right through her intentions, and I wasn’t going to give her the satisfaction of being right — Until now. I lied. I denied any lewd behavior on my part. I simply told them I was stuck on the other side of the drawbridge and had to wait for it to be lowered again. They bought it, and with that, I went in the house to shower and get ready for the day.
Ironically, later that night we had dinner on the beach in Menemsha. We stayed to watch the sunset and had a blast. We had no cellphone service out there because it is a remote part of the island. When I arrived home, I notice a message from the ginger mentioning seeing me on the beach that night. It was a little creepy knowing he didn’t take a ferry that day and saw me that evening. I was very grateful he didn’t walk up to me and say anything. And, of course, the following morning I had a request for a repeat, but there was no need to revisit that again.
I wasn’t on the island an hour, and I had already gotten myself into trouble. This was certainly going to be an interesting vacation…
Follow @onegayatatimeAt the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 