There’s Something About Harry…


My best friend, Harry, is a sex addict. Or at least that was the story we were going with, up until a couple of months ago when he miraculously had a “come to Jesus” moment (or rather more like a “I think I’ll try to be a good boy for a little while, just to see how long I can stand it” moment) and decided to stop sleeping with anything with a vagina and a car. For a while there, his bedroom was a revolving door of women, sometimes too many for me to keep track of, all vying for Harry’s love and attention. There were times I wish I could have warned some of these poor ladies, since nobody knows what a futile task it is to try to win Harry’s heart more than I do, but being his “bestie” I could only listen, often laugh (sorry – terrible, I know), and attempt, unsuccessfully, to beat some sense into his thick head. The truth is, it wouldn’t have mattered what, if anything, I had said to any women in his life, because there is just something about Harry that can make even the most sensible woman lose her goddamn mind.

I met Harry on Tinder over a year ago. I was obviously not shopping around for a best friend at the time, but nonetheless, shit happens and here we are. Originally, however, Harry and I matched and began texting back and forth one night in mid December. It quickly became evident that Harry was not my usual “type.” He was older than anyone I had ever dated, had children from a previous marriage (I had never dated a man with kids nor had I ever wanted to date a man with kids), and he was also culturally different – not that it was a big deal to me, but it just so happened, that as luck would have it, I had always ended up dating men who were the same religion and ethnicity as me. But Harry was pretty hot, and I was just coming out of a pretty exhausting ordeal with some other guy I had met on Tinder, so I really didn’t care much about any previous deal breakers or must-have’s. In fact, I was feeling pretty ballsy on that cold, December evening – so much in fact, that after initially turning down Harry’s request to meet him for a drink that night (seriously!? – we just started texting like 20 minutes ago!), I decided that since my usual overly cautious and overly picky style of dating hadn’t exactly been working out for me, perhaps I would try to do something totally out of character. I agreed to meet Harry that night. Fuck it.

I told Harry that I would meet him for one drink and for one hour. I had work the next day and I didn’t want to give the guy any false hope that he would be getting laid that night. The bar was empty and Harry’s eyes were piercing through me as if yearning to look deep into my soul, or perhaps just under my clothes. I can’t remember much about that night because I was just proud of myself for being more bold and for giving someone a chance. Well, kind of. I mean, I wasn’t seriously considering dating this guy, it was merely an exercise in taking more risks. Harry was nice enough and cute enough, but I was definitely not even trying to be on my game and I certainly came off pretty cold and disinterested, as he often reminds me. After an hour of small talk, I turned down his offer to walk me to my car, kissed him on the cheek goodbye, and was on my way.

The next day Harry surprised me with his persistence. I guess the fact that I wasn’t falling at his feet was a bit new for him and made me a challenge. I told some friends at work about him, citing all of the reasons why he was someone I would never date, but all I got were a lot of loud yelly voices telling me that I was crazy and needed to give this guy a chance. Suddenly I began to consider Harry with different eyes. Perhaps this is exactly what I needed! I mean every article that you read about dating tells you that you should stop dating a certain “type” and be more open-minded. Maybe if I dated the complete opposite of anyone I had ever dated before, I would finally have my happy ending. Hahahahaha!! Sigh..

I could not have been more wrong.

Harry started out strong – telling me all of the things that I wanted to hear. He was a one woman man, he was looking for a relationship, he wanted to get married again, and he would even be open to having another child if he met the right woman (these were all lies by the way, every last one of them – sorry Harry, but you know it’s true!). Pretty quickly he managed to suck me in with his smooth talk and slick charm. I found myself falling for this guy pretty hard, and I felt as if the feeling was mutual. But then, as luck would have it, situations outside of either of our control arose, and Harry ended up having to relocate. Suddenly the man I was dating was living 2 hours away – not the biggest deal in the world, but certainly not ideal.

What we lacked in physical proximity, we more than made up for with hours of daily communication. Harry became my morning wake-up call or text, we would spend the day texting back and forth, talk for several hours each night, and face time before bed. We began to develop a routine filled with silliness, private jokes, and lots of long, deep talks. He was going through a bit of a hard time and it made me feel good knowing that I could be there for him in any capacity, which he always expressed appreciation for. It had been a few months by now, and although it was not the perfect situation, I found myself really visualizing a future with this man. But then things began to get a little dicey.

The red flags began to pop up around early February. Harry had a penchant for being a very immature and dirty “fighter.” For example, if we got into an argument over something, he would block my calls and texts and ignore me for several hours. It was infuriating. And then came the issue of our “status.” Mr. “I am totally looking for a relationship” suddenly became Mr. “I have an issue with labels.” Harry said that he couldn’t handle the boyfriend / girlfriend label; that it gave him anxiety. He told me that he wasn’t sleeping with anyone else and that he wanted us to be exclusive, but that not having the label made him feel like he still had his “options open” and he needed to feel that way in order for him to not get totally freaked out (even though he admitted that if he ever pursued another “option” it would be considered cheating). There is nothing more romantic than having the guy you’re dating call you an option, let me just tell you. Ahem.

Clearly I should have cut my losses at that point, but that would have been too easy and too sane. Instead I decided to pretend that what he was telling me was totally cool with me and I continued to allow myself to believe that things were relatively great. After all, we were exclusive – so we were basically in a relationship! Semantics, right? Except that we weren’t.

One time Harry tried to end things with me. I was supposed to take my first trip out to see him right after he moved, a trip we had planned for a few weeks. I was supposed to drive up after work on Friday, but that morning he sent me a text telling me that he “couldn’t do this anymore.” He said he was a sex addict and he didn’t want to drag me down and do what he’s done to other girls to me. He said he was sorry but that it was for the best. And he said he was blocking me because he didn’t want to talk about any of it. I was irate. What 40 something year old man breaks up with someone like that, over text message? And then blocks them? It seemed like he’d probably used that move many times before on other poor girls with some pretty good success, but fuck if I was going to let him get away with it! So that night I decided to go full Glenn Close on his ass and I drove the 2 hours to his house anyway (the fact that I didn’t even hesitate still scares me – but clearly he was able to bring out the crazy in me.) When I got there he wasn’t home so I checked into a hotel a few miles away and had my friend text him that I was there. Eventually I heard from him and I went over to talk to him. Surprisingly he didn’t seem too put off by my psychosis (which probably should have told me something right there). I basically ripped him a new asshole and told him that if he wanted to end things with me that he would have to do it to my face like an actual grown-ass man. I deserved at least that much respect. A lot was said, some apologies made, he retracted his “sex addict” statement, saying it had just been an excuse, and foolishly, we fell back into our routine. In fact, oddly enough, that weekend brought us closer together and made our relationship better (pretty sure he never blocked me or canceled plans with me again after that…well not that often anyway).

The next few months were a long, drawn out game of cat and mouse between me and Harry. He would become standoff-ish and act emotionally unavailable, and then he would randomly send me a text message professing the deep and “scary” feelings he was developing for me or say something to me on the phone to indicate that he was falling for me. Every time I was ready to walk away, he would throw me just enough bait to keep me on the line. I began to believe that he really was as damaged as he told me he was, and that deep down he did have real feelings for me, he was just ill-equipped to deal with them. He had his share of baggage and was pretty jaded about relationships altogether, but I believed that with time and patience, we would eventually get there.

Well, we got somewhere, but never “there.”

Find out where me and the shit head end up next week in “When Harry Met Sally…and Kathy, and Sarah, and Rebecca, and…”

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2 thoughts on “There’s Something About Harry…

    1. Thanks so much!! I’ve been told (by Harry!) that my articles are too long, which is why I have been breaking them down into parts lately, haha.

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