One Gay at a Time

Now that I have a fair amount of dates under my belt, I feel comfortable meeting more men without much prescreening. Normally, I try to qualify them by talking a fair amount before meeting in person. Now, it’s worth it to save this conversation for a first date.

I came across a very attractive 25 y.o. on adam4adam.com. His profile was far from substantial. Play safe only. HIV neg and STD free — looking for same.  His name also had nsa (no strings attached) in it. This is not the arrangement I seek out, but at this point, I was having fun and not asking too many questions.

We exchanged a few messages over a decent time span. The conversation actually died to the point I messaged, “Hey there. Haven’t heard from you for some time. If I’m barking up the wrong tree, let me know.”

He responded with continued interest, and shortly after, I said, “I hope I’m not being too forward, but I’d love to meet up for a drink sometime. Toss me your number if you’re interested.” I got his number and set a date. We agreed to pick a location the following day as the workday was ending.

I texted him the day of the date to make sure we were still on. Nearly an hour passed. Just when I had about given up on him as yet another flake, he responded. He told me to meet him at 7:00. I purposely left my office late to arrive fashionably late. That would have gone well, except he showed up for the date a half hour late.

I waited for him at a high top in the dive bar he chose, Whiskey River. When he arrived, he apologized for being late and grabbed a beer at the bar. The conversation started slow, but picked up quickly once we got comfortable. I asked him why he agreed to go on a date with me. He said, “Because you asked me out for a drink. It was a nice change from all the guys looking for hookups.” When I asked him what he did, he told me he was unemployed and unleashed a story like I’ve never heard before.

He was born in Israel. After he served his military term for one year, he decided he wanted to explore the U.S. for 6 months. He left behind a boyfriend of about a year (a very complicated relationship). He ended up staying in NY working as a waiter. When a woman heavily flirted with him, he informed her he was gay. She introduced him to her other gay friend, and they all became close. So close, he and the woman married (took me a few minutes to realize for immigration purposes). This woman had fallen in love with him, but he realized this too late. They had a big falling out, and he moved out on his own.

That’s when he met a new man. They were dating for about a month when this man decided to take him to his Connecticut house. My date was expecting to be visiting a cottage, when in reality it was a mansion. This man was a millionaire 10 years his senior.

The whole time my date was telling me this story, he looked past me. His eye contact was unnerving. He periodically glanced back to me, but spent a majority of the date looking elsewhere.

So Wandering Eyes went on to tell me this man asked him to move to California with him for the winter. This was his typical schedule, and he wanted Wandering Eyes to come. W.E. left his job managing a hotel and his friends and moved to California.

He lived the life of a kept man. They even discussed marriage. He drove a Porsche, wore Armani suits, was waited on hand and foot by servants and went to galas, award shows and benefits, all the while not working. The millionaire was also very possessive over him. He read his emails and checked his phone periodically. W.E. had nothing to hide, so he allowed this behavior. He started to get bored with his new lifestyle and missed his NY friends,. He decided to plan a trip back east for a week.

Upon his return, the millionaire was acting very different and suspicious. When the opportunity for W.E. to read through the millionaire’s emails arose, he jumped on it. He discovered that while he was in NY, the millionaire had an affair with another man and even took pictures of the two of them in the bed he shared with W.E.

W.E. decided he wanted nothing to do with this situation moved back to New York. The millionaire did everything in his power to get him to stay, even asking for them both to have action on the side, and they would just stay together. No dice. W.E. was gone.

In the meantime, the woman he married was interested in marrying a new man and filed for divorce. W.E. came back to New York jobless, divorced, newly single and homeless (the millionaire allowed him to live in his Manhattan apt until he got back on his feet). I wanted to walk around the table and give him the biggest hug. My heart bled for him.

I learned so much about him from that story. His character ran deep. His friends told him he was crazy for giving up the lifestyle he had, but he was still able to recognize his own unhappiness and moved on.

We chatted for about 3 hours before we walked to a Starbucks for a coffee. There we talked about movies and one of his interests, comic book heroes. We discussed our favorites and why.

The time came for me to go home, so I walked him to his subway stop. He had the most beautiful eyes and lips. I had been staring at them all night. A majority of the night, all I could think about was how much I wanted to kiss them. However, when the time came, I lost my nerve. I hoped he would make a move, but he didn’t. We hugged goodbye and talked about a second date.

On my way home, I texted, “Hey. Prob supposed to wait til tomorrow to msg you, but not my style… Really enjoyed meeting you tonight. Can tell deep down you’re a really great guy… And you’re even hotter in person… I’d really love to see you again some time if you feel the same… P.S. I’m really awkward with goodbyes… Sorry… Felt like such a sh*t when I walked away…”

He responded, “No worries. I probably would’ve kissed you if you didn’t walk away… So maybe it’s not a bad thing that you did…”

This is very confusing. How would it be a good things I walked away without a kiss? “Of course it’s a bad thing! Wanted nothing more than for you to kiss me ;),” was my response.

His next text was much more reassuring; “Well… Guess we’ll know better next time.”

I told him I was happy to hear there would be a next time. Sadly, there never would be. We tried, but plans never seemed to work out. Things fizzled out, and we haven’t been in touch since…