Things weren’t exactly progressing smoothly in my mind between Smiles and I. In fact, things weren’t progressing at all when I come to think of it.

Instead of abandoning my relationship with him, I decided to put forth greater effort to ensuring its success. I’m not one to quit without a fight, so when Smiles texted me to ask how my day was going, I was quite elated. I told him it was going well and was anxious for work to be over. We made plans to go to dinner that evening after work. I was looking forward to it and was ready to make sure it wasn’t a repeat of our last date.

In turn, I asked him about his day, and he responded with an explanation. I explained I wouldn’t be done work until a little later, and I wasn’t sure exactly what time that would be. One of my coworkers was dragging his feet, and my day was beginning to drag on. It was a Friday, and I wanted nothing more than to see Smiles after a long day.

Smiles was running errands in my neighborhood and called when he was finished. I had a feeling I would be done shortly, but there really was no telling when I’d finish. Smiles occupied himself for some time. When he called again to check in on me, I was able to tell him I was about to be walking out the door. He was about to hit up Barracuda to have a drink with his bartender friends, but instead, we picked a place to meet.

I snuck up on him on the street and startled him with a big hug. We exchanged a kiss and started to walk towards Chelsea. We quickly found a spot to grab dinner. Smiles wasn’t drinking, but I certainly needed a drink. I ordered a glass of wine and took a big swig. I’d been talking up a storm from the time we kissed on the street. I was going to make sure the conversation flowed like a waterfall. He was well engaged all throughout dinner at Bar Baresco. I really felt very comfortable with him and was appreciating his company greater. It was night and day difference from the last date we had. I was realizing why I fell for him in the first place. No awkward pauses. No blank stares.

During my workday, I began drafting plans to build my new closet since I was moving. Smiles had much experience in this sort of thing, so I asked him for advice and to look over my plans. He gave his suggestions, and I appreciated his advice.

When we finished dinner, we hit up Barracuda. Smiles suggested it because he figured we’d say hi to his friends. When we arrived there, we found they weren’t working. Smiles ordered us two drinks. After relieving myself, we found a quiet corner to tuck ourselves in to sit and chat.

We discussed age and the ability to hang. He talked about how he used to be able to go out all the time all night long. We talked about growing older and looking forward to staying in and sitting on the couch on a Friday night.

We were growing even closer. As time progressed, I realized he was growing weary. I asked if he would like to get out of there, and he gladly obliged, but not before we played around with his scarf in about 20 different permutations around his neck and head.

As we walked outside, I proposed coming back to his place with him. He agreed. I thought I was sending a pretty clear signal of my intentions. We walked over to Seventh Avenue to hail a cab to no avail. I was not properly dressed for the weather. I was freezing. The Smiles did one of the sweetest things. He came up behind me and wrapped his arms around me to keep me warm. I reached up and grabbed his arms and brought him in closer. It was extremely romantic, and I wasn’t about to let this moment run away from me. It took a long time to get a cab, but I was relishing every second.

When we finally hailed one, we hopped in. He extended his hand beckoning for mine. He was winning me over big time! It was a complete 180. I was thrilled with his new-found affections. It painted a clearer picture of his true feelings for me. He was still interested in me. I was thrilled.

When we arrived at his place, he started cleaning. I kept yelling at him to stop. I didn’t care about the condition of his apartment. I would have liked to think of myself no longer as company, and more as companion. He sat on the couch, and I sat on his computer chair facing him while we chatted. After a while, I realized how ridiculous this setup was. I aimed to remedy it. I got up, walked over to the couch, moved the pile of papers from it, and sat next to him. He looked slightly uncomfortable by this, and I couldn’t fathom why.

He suggested we move to the bed. My goal was being accomplished. I was all too happy to move things to the bedroom. We climbed onto his bed. We talked and then began hugging each other. This morphed into spooning.

I was happy and hoping this would progress to sex, but I was sorely mistaken. After spooning for about ten seconds, he had his fill. He was ready to go to bed, and apparently I wasn’t part of that scenario. He went to brush his teeth, and was giving me all the signals it was time for me to go.

We said goodnight and exchanged a kiss at the door. Yet another night without sex. It was an enigma to me. I couldn’t figure him out. He spent the earlier portion of the night being utterly sweet and affectionate, but when it came time to end the night, the sparks were quickly doused.

I wished the night ended on a more positive note. I would have liked to go home a happy satisfied man, but yet again, I was debating in my head Smiles’ attraction to me…