In a new six-part series, Talking About That One Relationship, Jimmy Yitzak talks candidly about something we’ve all experienced… the relationship that messes you up good…

As we go through life, we all have that one relationship that fucks us up really well. Some of us have more than one. Luckily for me, I’ve only had one so far but it really did fuck me up. For years after I was haunted by it. Sometimes, I still think about it, even to this day. This relationship has had some effect on all my successive relationships. In the end I don’t regret going through all that pain because it helped me grow as a person but I never want to deal with something like that again. This is that story.

I had recently turned 25 and I felt that I was in a good place. My career felt like it was going somewhere. I had some money in the bank and I was paying off my credit card debt. I was, dare I say it, happy. There was something missing, however. Someone else. Now, I’ve always been a firm believer that a person can’t complete you; they can only complement you. I wanted to share experiences with someone.

I wasn’t the type of guy to go out the bars and meet people that way. How else was I supposed to find someone to date without being out on the scene and meeting people? The Internet, that’s how. I had been on free sites like Okcupid but those dates never seemed to pan out. It seemed like website only attracted the weirdoes. I was going on dates that made great stories for later but I wanted something more.

talking about that one relationship To get the full benefit, you have to pay for it. I thought that since you had to pay for the site people would be a bit more serious about dating. I took precious care with setting up my profile. I applied the same rule that I used on OkCupid. I don’t answer messages that are just “Hey, what’s up?” or “How was your weekend?” I mean, come on. Great time and care has been taken to make this profile. You can at least show that you’ve read it and comprehended it. I was a bit stricter about actually going to meet people this time. I’d make sure I’d have some good long conversation before the first date.

I stumbled onto this one profile of this guy who seemed really intelligent and thoughtful, not to mention very attractive. I wanted to craft a message commenting on what I read. For whatever reason, I was having trouble so I put it off. Trying to craft it in my head on the subway ride to work or at work. I’d look at his profile again and see if anything new came to mind. He must see that I’ve checked out his profile numerous times. How embarrassing! Then, out of the blue, he messages me. I read the message and it says, “You’re so fucking cute!”

“He messaged me!” I thought. I may have even said that out loud. But he broke my rule. Then again, I had really wanted to message him in the first place. But he broke my rule. This was the conversation going on in my head. I decided to just use his less than ideal message as a springboard to more thoughtful conversation. It worked! We talked for a bit online before we decided to meet for a drink.

We exchanged phone numbers and were sending each other texts arranging when and where to meet. I recommended a funk bar I knew in midtown. He had recently moved to the city and didn’t know anywhere. He was still staying with his brother but was looking for a place of his own. The day finally came and I was nervous. I wanted to put my best foot forward. I mean this guy seemed great from his profile. He was good looking, artistic, creative, and funny. On my lunch break from work, I went to the shop and bought a whole new outfit. Ok, I feel good. This is going to be good.

The working day finally ended and I went to go meet him. I got to the bar first and slightly early so I sat at the bar and, well, I felt awkward. I had never been good at being in a bar alone but I sat there and waited. He was now late. My phone vibrates. It’s a text message from him. He had been running late from work but he was on his way. I wait a few minutes more and he walks in. The tall handsome stranger who looked great in his pictures looks even better in real life. Wow! And he knows how to dress himself.

After I picked my jaw up from the ground, I think I tried to go in for the hug, realized what I was doing and quickly changed to the good ol’ handshake. We sat down and ordered drinks. I ordered a scotch neat with some water. He was instantly impressed and ordered the same. Our conversation came easily. There were no awkward silences or hesitations. We ordered another round. We ordered some food. Now, if you’ve ever drunk scotch before, you know that after two scotches you start to feel a little tipsy. “Let’s go for a walk”, I recommended. We left the bar slightly drunk and went for a walk.

I steered up towards the Hudson to a pier that I liked to sit and watch the boats go by. We talked the whole way there. The chemistry was palpable. We found a bench and sat facing each other. Then that moment came. We both felt it and we both leaned in for a kiss. Magic. We kissed some more and then we kissed again. We full on made out. Then he said, “Let’s go back to your place.”

To be continued in Part II of Talking About That One Relationship – That One Relationship: Early Days…

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