An awkward night…

When I woke up at about 3pm, I saw Adam’s text (see There’s always a red flag…). He texted to say it was nice meeting me and we texted back and forth for a bit that day. The next day, he texted to ask if I was free later in the week for dinner. I agreed. I was excited, yet still unsure about him. I had a really good time, but I could tell he’s way more conservative than I am, that plus the whole living with the ex girlfriend thing was a huge red flag. Other than that though, I had a really good time and it was definitely an unforgettable night of adventures throughout the city.

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On the day we were supposed to meet for dinner, I was almost out of work and I still haven’t heard from him to confirm. I know he’s probably been out of the dating game a while, being that he’s recently single and all, but when a guy doesn’t confirm, I always have the urge to just cancel on them. I let it slide. I texted him around 4pm saying I was going to be working longer than expected and to tell him I would be running late. This would buy me a little extra time to get ready, which I needed, while also being a sly way to confirm that he still wants to get dinner. He responded saying that it was no problem and he’ll see me there.

That evening, I got there right on time, went to the bar of the restaurant and ordered a drink. The bartender took my card and assumed I was opening a tab, which was fine, but you’d think she would ask me before just holding onto my card. I was there a good 5-10 minutes before he finally arrived. He apologized when he got there and then sat next to me at the bar. The bartender came by and asked if he wanted a drink. He mentioned that we were there for dinner, she asked if we wanted to stay at the bar and order or get a table. He said the bar was fine. OK… so he set it up for awkwardness right from the start. Not confirming. Running late. Agreeing to stay at the bar. I know he’s been out of the dating game, but dude, all of that is adding up to make me really annoyed.

He started out with small talk. Nothing too exciting. We chatted, he told me about his EMT training, I told him about work, we drank, hardly looked at the menu. The bartender checked on us a few times before we finally got around to figuring out what we wanted to order. We continued to small talk. Still nothing too exciting. He’s very dry and kind of monotone. I think the newness of him has already worn off and was only made more interesting a few nights earlier because of the amount of alcohol we had consumed.

When the food arrived, we ate, talked, ate. We were there a good three hours before we realized the time and asked for our check. And that is when I remembered the bartender already had my credit card. Adam asked for the check and she had said, “Oh, do you not want it all on your tab?” Adam looked confused, then I explained and then we agreed to split it. She seemed a bit annoyed, but it was kind of her fault for assuming in the first place that everything was going on my card and for even starting a tab without actually asking.

We left the bar. I was tired and tempted to call it a night, but then he asked if I was still up to hang out, I agreed. I was holding onto hope that I would regain that spark from a few nights earlier. We walked. He had no plan of where to walk, we just walked. It was a neighborhood he grew up in, so he told me some childhood stories which were sweet to hear. Once we walked without further plans for about 20 minutes, I told him to turn left. He didn’t know it at the time, but I was leading him to my place.

On our walk, we walked right past a sex toy store. He made a point to say something about how his friend and his friend’s wife are very open about their sex life. I told him I am too and I think that sex is a very natural and healthy thing. He kind of shut up about it. I don’t know if this was a turn on or turn off for him at that point. I think he wasn’t expecting that, plus he seems very reserved and a bit prude from what I can tell thus far.

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As we got closer, I told him I lived a few more blocks down. He called me out, “Is this just a sneaky way to get me to walk you home so you can end the night?”

Although that wasn’t the case, I was tempted to say yes, but then told him, “No, that’s not what I was doing. You obviously didn’t have a plan of where or what to do, so this is my way to be sneaky to get you to come to my roof and have another drink with me.”

He laughed and told me that was smooth of me. We went upstairs. I gave him a tour of the place. We went to the bar, I poured us each a whiskey ginger ale and then we headed to the bar. We looked at the view and chatted briefly. He made his move. We started to make out and within minutes, two of my roommates opened the roof door and walked in on us. I pulled away and laughed, then introduced Adam to my roommates. We all hung out for a bit while they smoked their cigarettes. Once they were done, they went back downstairs and Adam and I went right back into making out.

At this point, things got hot. He started to work his hand all on my body and up to grab my breasts. As he felt me up, he started to kiss down my neck and eventually kissed down to suck on my nipples. I was so worked up at this point, yet still exhausted, yet still unsure and leaning towards a no with him. We continued to feel each other’s bodies and kiss until my roommates came up for yet another cigarette break, but this time, they walked to the other side of the roof away from us.

We stopped making out. I realized the time and said I should probably get going to bed soon. He said he would leave whenever I wanted him out. I looked at the clock, it was about 11:30, I told him midnight would be fine. My roommates didn’t seem to be leaving this time, so Adam and I just kind of hung out awkwardly for a bit longer before I caved and asked if he wanted to go to my room.

He agreed. I then gave him a caveat and said there will be no sex and he’s still leaving at midnight. He laughed and still agreed. We went downstairs and went to my room. We got back to making out. I got on top and straddled him. As we were making out, he started to rub my back, which felt amazing, so I told him to keep doing that. What was a make out session, quickly turned into a soothing back massage and cuddle session which I ended up falling asleep on him as he rubbed my back.

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I woke up around 12:20 and realized what had happened. I saw the time and said I should probably get ready for bed. He put his shoes on and made his way out the door, on his way out, he said we should hang out again soon. I agreed, but wasn’t really that interested anymore. I would have hung out with him again if he tried, but he never did.

This was a month ago. And we went the entire month without talking, that is, until this past Wednesday he invited me to a party for Friday. I told him maybe I could show up later, but I had another party to go to. I ended up not being able to go, but told him we should catch up soon. The ball is in his court. I’m not really going to push hanging out again, but if he hits me up, I probably wouldn’t turn him down.

We’ll see if this goes anywhere… Sometimes you should leave it at one night of romance, this is probably one of those times.

Yours Truly,
Kallie Pygus

 

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