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When I was in college, I was obsessed with this one guy. OB-SESSED.  He had a girlfriend, but he was just so dreamy, and I had concocted this fantasy that he would break up with her and be with me.  (Shut up. I was 18.)  I was messed up in the head over this fool for the longest time, convinced he would fall in love with me if he just knew me well enough.

That did not happen.

What did happen was that I used to walk past the retail store where he worked just so I could catch a momentary glimpse of him and then scuttle away like a cockroach. My friends yelled at me for doing this. I was in a miserable and unhealthy place in my life: many, many years away from getting control of the anxiety and depression that shredded up my late teens and early 20s. I was in no place to realize — as I later would — that if a man doesn’t want you, he doesn’t want you.

Fast forward 10 years.  I had dated other men over the years and had had actual, you know, two-sided relationships. While my feelings for this guy had cooled drastically compared to what they once were, I still held a teeny, tiny candle for him. He was still that guy for me. So when I was single and he asked me out on a date, of course the 18-year-old Jessica that still lived inside me was curious.

And it turned out to be the weirdest fucking date I’d ever been on.

Some people think that talking about exes and past relationships on a first date is a big no-no. That’s so wrong. Talking about exes and past relationships on a first date can clue you into important shit. Case in point: me asking how his last relationship ended.

It had ended two weeks ago.

And she had taken out a restraining order again him.

Because he had shoved her.

And all this had happened right before they were planning to move in with each other.

My eyes widened bigger than the dinner plates on the table in front of us. Why are you telling me this, I thought, trying to keep my face expressionless. We are on a first date. Why, why, why are you telling me this? I mean, I had asked, but still.

“If you want to leave right now, I won’t blame you.”

I didn’t know what to say to that. Getting up and leaving the table in the middle of a date seemed awfully melodramatic, like something that only happened in soap operas. He just told me he had shoved his ex-girlfriend, yet the Miss Manners WASP deep down inside me wouldn’t let me leave. But at the same time, I was legitimately horrified. There was no way, no way at all, that I wanted to see this person on a second date.  It wasn’t just that his behavior he was telling me about turned out to be a disappointment, but I resented how he had reached out to me just two weeks after it had happened. Me, someone he hadn’t seen for 10 years.

Of course, I knew there was a reason this guy had appeared out of nowhere. A dude who knew that I was obsessed with him 10 years ago doesn’t just come out of the woodwork; I had met up with him suspecting he was on the rebound. But I had not been expecting this utterly shit-tastic tale.  Clearly he was not in the headspace to be dating. He was in the headspace for sympathy. He had answered my question about his last relationship honestly, yes, but it concerned me that he even thought going out with me two weeks after this had all went down was a good idea. What, I thought to myself, makes him think that I would be sympathetic? Just because 10 years ago I had a crush on this guy doesn’t mean he can come to me now and boo-hoo on my shoulder. 

did want to leave right then, to pack in it, to stop this exhumation of this old flirtation. But I stayed at the table through dinner and dessert. I was not going to give him the sympathy that he asked for, but I was going to give him a piece of my mind. I told him I thought he needed to be in therapy and that he wasn’t read to date yet. That he wasn’t even ready to think about dating.

And I told him — honestly, in fact — that it was good to see him. Because it was good to see him that night; his fucked-up story, his fucked-up-ness, put an end to something that I should have  been healthy and mature enough to close the book on a long time ago.

Contact the author of this post at Jessica@TheFrisky.com. Follow me on Twitter and Tumblr.

[Image: Thinkstock]

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