Out of the entire roster I built before I went away, I had the highest hopes for one in particular. His picture on Grindr was of his face. What a nice change from the torsos that scattered my screen. And, not just any face. This man was sexy. He had dreamy eyes and perfect lips. I couldn’t wait to meet this man in person.

When we first started chatting on Grindr, I favorited him. I noticed one night he was very far away and asked where he traveled to. I learned he lives in my old neck of the woods in Pa. He explained he lived out there, worked in the city, and one or two nights a week, he would buy a hotel room so he didn’t have to commute. I suggested we grab a drink sometime. “Def man. I’m game for that,” he responded. And with that he gave me his phone number.

We were unable to set up a time for drinks before I went on vacation. He was polite enough to hit me up while down there to see how I was doing. One night, while texting each other, he decided to pick up the phone and call me. I couldn’t answer because I was riding in the car with my family, but he left a very sweet message. He gained a lot of points in my book for calling that night! It meant a lot to me.

When I returned to Hoboken, we finally set up a night to grab a small bite and drinks together. I already liked his style. He suggested tapas because if the date didn’t go well, we weren’t stuck together He booked a hotel room for Wednesday night, and I picked a restaurant. He was my fifth date in four days.

The night of our date, he was running late. He apologized and explained this was standard protocol for him. I told him not to worry about it because I was usually the one running late. To kill time while I waited for him, I strolled through Eatily. When the time for out date was approaching, I walked to the restaurant to get us a table. When I arrived at Boqueria in the Flatiron District, there were about fifteen people standing in the rain waiting to go inside. I didn’t panic. I tried the backup restaurant, Sala 19, but they had a 45 minute to hour wait. I called (Let’s call him “Pillow” since his lips looked like two little pillows I couldn’t wait to smooch), and told him of the predicament. I also explained I would be trying to find a new place and would meet him on the street corner. I did some research and found two other places. The first couldn’t seat us for another two hours. The second, Aldea, had no wait. We met and shook hands, I suggested we go there since it was two blocks away. He agreed.

When we arrived at the restaurant, I almost suggested we leave. It had awful ambiance, and NO ONE was there. It already made the date feel awkward. They sat us upstairs, and we both ordered drinks. When my sangria arrived, it was clear, served in a Tom Collins glass and topped only with green grapes. I don’t think it was sangria, but it was good, so I drank it. We both struggled to find anything on the menu we liked. I am NOT a picky eater, but this menu was a challenge! I suggested we just leave after the first drink and find a bar. He said we should stay and we ordered the almonds and olives plate, as well as a shrimp appetizer. We talked about the possibility of hitting up a bar after dinner as well.

The conversation started off dry and forced. This date I had such high hopes for started off on the wrong foot. I didn’t know how to rescue it. I never realized how much the setting could ruin a date, however, we were able to find some common ground. We both worked in advertising. I was happy I never asked him about it before, since it gave us something to talk about to break the tension.

When we finished, they brought us chocolates, we paid and went back out into the rain. We started walking up Broadway towards my office and somewhat towards the hotel he was staying at. As we passed the Ace Hotel, I stopped him and asked if he still wanted to get another drink or did he need to get back to his hotel. I was giving him an out. He said he’d be down for another drink, so I suggest the Breslin at the Ace Hotel. I had been there many times and really enjoyed the vibe there. I was also glad he wanted to continue hanging out with me.

There were no seats available at the bar, so we found a nice plot of space in the corner to lean against the wall. Once we had our drinks, things got a lot more relaxed. I said, “We should have just come straight here. That place was awful!” He told me I shouldn’t worry about it. We stood there for another round. With every drink, the mood got lighter, and I became more attracted to him. After the second round, he asked if I minded if he have a cigarette. I said, “Only if you don’t mind giving me one.” We stepped out into the rain and found a doorway to huddle in to smoke. We talked some more and the body language was very positive. I debated if I should have kissed him right then and there. But I didn’t of course.

We went back inside and managed to find two stools. We sat facing each other and he began to lean in much more when we spoke. His body language was becoming more and more provocative with each sip. After that round, we both had another cigarette. When we returned this time, the only space available was at the bar. I ordered us another round of drinks and an order of fries considering we basically had olives for dinner.

I was having a good time with him. He was charming, had a good job, family oriented, very good-looking, mature, etc. It was about time I finally had a good date. The whole date, all I could think about was how much I wanted to kiss him. Around 11:30pm, we finished our drinks and closed out the tab. We spent the last four hours together. I wasn’t sure we’d make it past the first forty minutes when we stepped into the first restaurant.

I told him I would walk him to his hotel since it wasn’t far from my office, and I had to return there to get my things. When we got to the front of the hotel, I expressed to him how much I enjoyed the night first verbally, and then physically. I leaned in for a kiss and got exactly what I was hoping for all night. I pulled back and said, “And a good kisser too. It’s a shame I waited til the end of the date for that!” With that, we started kissing and embracing more while the doorman stood watching us. Finally, we both pulled back. As I started to walk away, I turned back and said, “We do this again? Soon!?” He nodded in agreement.

I walked away with the biggest smile on my face. What started out bad, ended really well. I couldn’t have been happier. On my way home, I texted him telling him: “I had a great time with you tonight!” He responded, “More to be had. I had a great time and now that we met, I can loosen up a bit.” Then we got into the conversation of the compatibility of our astrological signs. Then he said, “Yea. I wanted to bring you up, but it’s a first date. I try to be reserved. LOL Did I want to? No. But, I was good.”

I was thrilled. This meant he was really attracted to me and wanted to start something real, not just a hookup. I didn’t want to get ahead of myself, nor did I want to put all my eggs in one basket, so I didn’t toss the roster out just yet. But, I certainly had a front-runner.

That weekend, I texted him a few times, but got no response. I wasn’t thrilled with that sign. I questioned if it was just the alcohol talking after our first date, but I didn’t panic. I would see if we could meet during the week again when Monday rolled around…