Posts Tagged late night

Testing Boundaries

Once again, today is another double post to make up for lost time. If you are just visiting for the first time today, scroll down to the previous story to keep up with the timeline. Enjoy!


It had been a long work trip. I didn’t have any spare time for anything fun other than work. The one hour I had free, I spent on the treadmill trying to get back in shape for the rapidly approaching warm weather.

After my meeting, I sped to the airport. I wanted to get home so I could start my weekend off right. I began texting everyone back home to see what they were up to so I could be efficient with my time when I landed. I sent out a flurry of texts and received a few responses before taking off. I knew at least a few people were up for drinks at the bar. I also decided to take care of my pre-game at 30,000 feet. I ordered two scotch on the rocks to help get me started.

When I landed, I got more responses to my texts. Some people were too lazy to go out. They received harassing phone calls from me urging them to sack up and join the able-bodied and willing. It was no use. I also texted my Grindr friend who recently moved to Hoboken from the city — Much closer to me. I asked him if he wanted to check out the Hoboken scene. I warned him it would be all straight bars, but he was down.

I picked up some food at the airport I could eat in the car on the way home. When I arrived, I quickly showered and got dressed. My friend took a little longer to get ready, so I had to wait for him a bit. I was getting messages from my sister and friend who were at the bar waiting for my arrival. I told them to keep their pants on… I was en route.

I met my friend on the corner and walked with him to my local watering hole, McSwiggans. I told him about the bar as we walked. He asked how my trip was, and we continued the small talk.

I hadn’t told anyone I was bringing a guy with me. They were a bit surprised. But, I wasn’t bringing him as a love interest. I was bringing him as a new neighbor and friend. He didn’t know Hoboken, so I thought I could show him around a bit. I also knew he was normal enough he would fit in. I introduced him to everyone, and we got beers. I spent a lot of the night chatting with him, but mixed in with my friends/sister as well. As the night progressed, my sister grew more and more intoxicated. She started rubbing her a$s on me like she does with people when she’s drunk. It took a lot to get her to stop.

After some time, I got a text from one of my teammates from college. He was in town at another bar, so I gathered everyone up, and we made our way to Black Bear. He was there with his new girlfriend and her friends. When we arrived, I needed to relieve myself immediately. He came down the stairs and joined me standing in line to hit up the bathroom. After we all finished using the facilities, we made our way upstairs. My group grabbed a table, and my friend dragged me over to meet his group. He introduced me while my Grindr friend followed me. His girlfriend was already three sheets to the wind and shouted into my ear, “Is this your boyfriend?” I explained he was just a friend, and we all continued chatting. When I realized I was neglecting my other friends, we made our way back to the other table.

By then my sister was wasted, and she needed to go home. Luckily, one of the guys in the group who is utterly chivalrous, volunteered to escort her home since they both lived uptown. I said goodbye to both and was left with P and my Grindr friend. When my Grindr friend went to the bathroom, I explained my predicament to her. Until this point, we were just friends, but I wasn’t sure if maybe we could be more. I asked her if I should make a move.

“Why not!? What do you have to lose?” she asked. I told her I liked having him as a friend, and if I crossed that line, I wouldn’t have a friend anymore. I wasn’t sure which I would rather have. A new friend or a new guy to date. She still suggested I go for it. I decided I would make a game time decision later.

I felt like it was mine for the taking. He always seemed interested but who could really tell? I was purposely putting out the friend vibe, but I think if I escalated things, he would be interested.

The night was dragging on, and I was tired. We closed our tab and made our way for the door. P lived in the opposite direction of my new neighbor and I. Furthermore, we decided to stop at Cluck U and get a late night snack before heading home. When he asked if we were eating there or somewhere else, I volunteered to go back to my place.

When we walked into my apartment, we sat at the counter eating and talking. When we finished, he needed to use the bathroom. I moved over to the couch in hopes he would as well when he came back into the room. He didn’t get the hint. He sat back down at the counter until I suggested he join me in the living room. When he did, he sat in the chair next to the couch. This was going to take some work.

We talked some more before I finally moved to the chair and said, “I hope this isn’t out of line, but…” and I laid a big kiss on him. He totally kissed me back. It was great. Taking the risk paid off. When I pulled back, I asked him, “Did I surprise you?” “Well… YEAH! Of course I was surprised. I just thought we were going to be friends,” he replied. “I know. I was putting out that vibe on purpose. I wasn’t sure what would come between us,” I told him. He just smiled, and we kissed again…

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The Game — Hard To Get

As predicted, Monday was the day from hell. We had a huge pitch on Tuesday morning, so it was constant work until the end.

There was already no chance Smiles and I would see each other. However, we did get to chat on the phone briefly. He had to do work with his film, and I would be working until the wee hours of the morning to finalize the content for the pitch. I didn’t end up leaving my office until 1:30am.

I really wanted to see him Tuesday. I wasn’t going to be around the rest of the week, and whenever I have a long work pitch or long work trip, I look forward to decompressing with a sexy guy, even if it doesn’t involve sex. I asked him if we could do something, but he already made plans.

I was heading home Wednesday for my grandfather’s funeral. It was going to be a while before I got to see him again, and I was really disappointed. Things were really getting strained between us, at least on my end. We weren’t having sex as often as I’d like, and I was constantly on a roller-coaster of emotions. Smiles would pay a lot of attention to me and make me feel great, and then retract and shy away from me. I didn’t know how much more I could take it.

I decided I was going to play hard-to-get. I wasn’t going to text or call at all. If he still wanted to see me, he was going to have to put in the effort. I was at my emotional breaking point.

This was no easy task for me. I struggled with it. I carried my phone with me everywhere I went in case he tried to call or text, but it was silent. Part of me wondered if he thought it was a very personal family time, and he just didn’t want to bother me. But, the bigger part of me thought he had other things with which he was preoccupied.

Finally, Thursday he texted me to see how I was doing. It was progress. He was texting to check up on me, and I appreciated it. I texted him back after some time passed.

When Friday came about, he called and left a message. It was impeccable timing. I was just about to walk into the funeral parlor when my phone began ringing. After the viewing, I stepped out from the family gathering and called him back. We had a nice conversation.

The following day, I went to the funeral. Afterwards, I came home. I have awful cell service at my parents’ house. I finally managed to get signal by using the Wi-Fi. Ironically, right after I texted him, we lost power in the snow storm, so if he responded, I couldn’t read it if I tried.

I was home with no power, no internet, no phone and no TV. It had snowed about a foot outside, so we were trapped. On top of it, I was missing the Halloween festivities with my friends back in Hoboken. I wasn’t heartbroken about that, but I was disappointed. Instead, I spent the day shaking snow off trees so the branches wouldn’t break.

I was really feeling ignored overall by Smiles. The time away wasn’t a good thing for me. It was making me realize how little attention he was paying to me. I started to think about some of the other prospects I had spoken to. I could have pursued LES, but he was young and lived in an inconvenient part of town. There were a few guys who were still sending me messages on OKCupid. While I wasn’t seeking out anyone new, I maintained communication with them. I was now beginning to think about them as prospects. All I knew was I deserved better. Was I just jumping the gun? Was it still early with him? I personally thought we should have been over that hump, and if he was interested in me, he’d want to spend more time with me.

When Sunday arrived, my sister and I made our way back to Hoboken. It was a bit of an adventure with the snowfall and trees laying across the road. Once I got back to Hoboken, I hopped on Facebook. Smiles messaged me, and I learned he lost his phone. He told me about going out for Halloween and how he lost it. We made plans to grab brunch, and I made my way into the city. I didn’t forget about the lack of attention he paid me, but I tried to concentrate on the moment at hand. I was going to proceed with skeptical optimism. It was the only way I was going to keep my sanity.

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The Ex’s

Still reeling from the high of a hot successful lunch date, I was pleasantly surprised that evening by the return of my belongings from N. Before he came by, I made sure I looked great. I threw on a tight tank and some gym shorts. I had been going to the gym and beach a lot and wanted to show him how good I looked. Little messed up? Ehhhhh probably… Don’t judge. We’ve all been there.

After letting him in the door, I returned to sitting on the couch. He came and sat to chat a bit. We discussed how things were going and made small talk. It was nice. We were being pleasant. I was shocked too. Not once did something catty come out of his mouth. It appeared both of us finally moved on. This was the beginning of a beautiful friendship. He couldn’t stay long. He handed me my clothing to check if he got it all. It appeared he did. I put the clothes down and he came in for a hug. It was nice. I liked hugging him. Not in a romantic way, but in a friendly way. I cared about him. I feel people are too afraid to hug these days. He even turned his head and gave me a peck on the cheek. It was very nice.

He wouldn’t be the only ex I would see that night. I had plans to see the second half of the final Harry Potter installment with Broadway. We watched the first half together right before we broke up, so I thought it would be nice if we finished the series together. He agreed.

True to my own style, I was exceptionally late. He asked me to get to the theater early to hold seats for us. It was a late showing, but it was also a new movie. The theater would be crowded. As I was running to the theater, I was texting him to calm his nerves. If we didn’t have great seats, he would wait to see it another time. This was important to him. It also bothered him because this was something I did all the time when we were dating. I have a hard time being on time for things, “but at least I’m consistent,” I joked.

I got into the theater and found us seats. He arrived shortly into the previews, and we sat back for the movie.

Earlier that day, he invited me to crash at his apartment after the movie since it ended at 1:00 in the morning. I graciously accepted since I knew how easy the commute from his apartment was. I also knew he was dating someone, so there wouldn’t be any temptation for funny business from either of us. I had no desire to revisit that past, but the thought crossed my mind wondering if he would.

On the walk home, we talked about our dating lives. I told him about all my failed dates, including the self-centered dermatologist. He updated me on his drama and the recent end of his relationship with the guy he was seeing. We were both in the same boat. It was interesting too, considering months earlier he said I wasn’t a priority in his life. I wasn’t mad about that. I was happy to see him moving on and trying to find a man. I just found it interesting.

Since the last time I spent the night in his apartment, they had done some major remodeling. It was nice to finally get to see all the hard work he put in to the place. I was happy for him. When we were both too tired to keep our eyes open any longer from talking, he set me up in his empty roommate’s bed and went to sleep.

I was just happy we could be good friends and share a movie together. We talked about going out to the bar together. Now that we spoke about seeing other men, he would be able to see me hitting on a guy at the bar. We were in a good place. It gave me hopes for N and I. I was finally making great progress with the two men who used to rule my world…

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