When Harry Met Sally…and Kathy, and Sarah, and Rebecca, and…


After my psychotic episode things were really good between Harry and me for the next three months. We had fallen back into our normal routine and I did my best not to pester him about our “status” and to just go with the flow.

When I backed off a bit, Harry became more open about his feelings. March, April, and May were probably our best months. Harry was sweeter and more open than ever before. We spent a lot of time marveling about how we seemingly had it all with one another, which had been a rarity in both of our lives. We had this amazing friendship where we could talk about everything and anything and we would never run out of things to say or have any awkward silences. We had amazing sex – intense, passionate, and insanely satisfying. We were also each other’s biggest fans and biggest cheerleaders. Nobody could make me feel better than Harry, and Harry knew that he could come to me for anything and that I would never let him down. The only thing standing in our way were his “issues,” but even those seemed to be subsiding. We would talk about the future, things we wanted to do, places we wanted to go. He introduced me to his children, first through Face Time and eventually in person. Even though they were told that I was daddy’s “best friend” it was still such a major milestone for both of us. Seeing him with his kids made me fall even harder for Harry and I began to imagine what life would be like if we were truly together.

After a few really solid months and an amazing weekend away together, I thought that Harry was really beginning to show signs of emotional growth, so I brought up our relationship status again. He was firm about not wanted to be “official” but I was just as firm about the fact that I had done things on his terms this entire time. We were not dating other people and we were technically boyfriend and girlfriend without the title. Even our families and friends knew about our relationship. What was the big deal? Harry told me that he had cheated on every woman in his life and he was worried that he would do that to me. I told him that we had basically been in a relationship this entire time and he hadn’t cheated on me and that I trusted him. Finally he caved and he agreed to make things official.

He broke up with me exactly one week later.

I was at work when I got the text, “We need to talk.” My stomach dropped. I knew what he was going to say before he even said it. He went on to say that he couldn’t handle this, that if we weren’t going to get married (because he was NEVER getting married again) than what was the point? He didn’t want to waste my time. He didn’t like feeling trapped. Etc., etc., etc. I was heartbroken.

It took me a few weeks to get over hating Harry. When we talked he told me that he didn’t want to be in a relationship; he didn’t want to be committed to anyone. Being my boyfriend for one week made him realize that he wasn’t ready to be exclusive. He cared about me and wanted to continue seeing me, but he wanted to be able to date other people. If I wasn’t open to that, then he would rather end any romantic relationship completely in order to be able to stay friends. He stressed to me how my friendship was more important to him than any other aspect of our relationship. Because of my feelings for him, I agreed to try. A part of me still hoped that if I gave him enough time, he would eventually see what we had and he would change his mind. Stupid, I know.

One day he called to tell me that he had re-activated his Tinder account. It was only for a “competition” that he was having with his friend; a “joke.” He wasn’t actually planning on meeting anyone… Yeah, right. It took about two weeks before Harry told me that he was going on a date. He was really pushing the boundaries of this whole friends with benefits thing, and I was letting him. Inevitably Harry actually began “talking” to several women and it became clear that he was going to follow through on his plans to see other people.

The night that Harry went on his first date I spent hours pacing my living room. He had told me he would text me from the bathroom (sick, I know) but I hadn’t heard from him. He was supposed to be leaving by 8 pm to head home and it was nearly 10 o’clock! I was sick to my stomach. Harry finally called me at about 10:30. His date had wanted to go somewhere else after coffee and he ended up driving her home. After a little probing, he finally admitted that they kissed goodnight. The emotions that I had stuffed deep down into my core came to the surface in a guttural cry that I could not hold in any longer. I lost it. The thought of him actually kissing another woman literally made me nauseous. I thought I could handle this, but I was kidding myself. I told Harry the next day that I couldn’t do this anymore. I wanted so badly to just cut him off and be done with it, but the thought of not speaking to Harry every day made me feel empty. I told him that I just wanted us to be friends. No benefits, just friends.

Harry joined a bunch of other dating sites now that he had total freedom, and the next few months were probably the most sick and twisted of our relationship. He was dating with a vengeance. Talking to six girls at a time was becoming the norm. After work each day he would give me the lowdown on all of his “relationships.” Initially he didn’t want to tell me anything because he didn’t want to hurt me, but being the masochist that I am, I needed to know every last detail. I told him that I didn’t want to be lied to. If we were really best friends, then he would have no problem telling me everything. He eventually complied. He would send me screenshots of text conversations, forward me dirty pictures that they sent to him, and we would talk about and laugh at how crazy they all were. Women would talk to him for 20 seconds and agree to drive to his house and cook dinner for him. He was getting laid left and right. Oddly enough I was somewhat ok with this, probably because I knew that this was just sex to him. I mean, we would make fun of these “pathetic women” (the irony of me calling anyone else pathetic is not lost on me, I can assure you). It wasn’t like he had feelings for any of them! In fact, as Harry had always told me, if he was capable of being with anyone, it would be me. He just wasn’t capable of anything deeper than a sexual relationship. There would be times when things would build up in me and I would cry to him on the phone, wondering why I wasn’t enough for him. He would always make it clear that it wasn’t anything about me, it was him. Very cliché, I know. He would tell me that he wouldn’t allow himself to think about me like that because there were feelings that he didn’t want to “deal with.” He told me that our relationship reminded him of Harry and Sally – they were the best of friends and they dated other people, but there was always something there between them. Sometimes, he said, he imagined that we would end up like they did, if only he could get over his issues.

Over time the benefits worked their way back into our friendship. I mean, we couldn’t realistically keep our hands off of each other when we saw one another- it just wasn’t possible. And sleeping together definitely muddied the waters. I would get jealous and upset and we would fight. Things were confusing, as he would make me feel like there was this amazing connection between us when we were together and then he would fuck another woman hours after we would part ways. He was sleeping with women but still texting me sweet things every once in a while. I was hanging on by a thread. Eventually I decided that I needed a time out in order to get my head on straight because this shit was getting ridiculous. Our relationship was beyond fucked up. This was in early August. We had plans to see each other later on that month, so I told him that I needed to not communicate with him for the three weeks leading up to that time and that when we saw one another we would sit down and talk about things.  Those three weeks without him were the longest weeks I can remember. Both of us slipped up once or twice and sent text messages, and we even had a phone conversation, but mostly it was silence. Deafening silence. I realized that having Harry in my life, in whatever fucked up form, was better than not having Harry at all.

After the most miserable three weeks it was great to see Harry again. We talked a bit about the fact that we were not in the same place. Emotionally, he would never let himself get there with me, even if he wanted to. He wanted me to be comfortable, so if it needed to be just a friendship then so be it and if I was ok with it being more once in a while than we would take that as it came. A couple of weeks later I went to an event with him as his “date.” We had an amazing night together, and after a couple of glasses of wine Harry admitted that he often thought about me and us, and that he wished that he wasn’t as fucked up because he knew that we had something special. He said that night it felt like we were in a relationship and that it felt good imagining me as his girlfriend. Even though I knew it was the wine speaking, it still felt amazing to hear that l had a piece of Harry’s heart, despite his valiant efforts to protect it from me.

Harry posted pictures online of us at his event the next day. One of his exes saw the pictures and began sending him a bunch of crazy texts. Harry took pictures of the texts and sent them to me, laughing about how insane she was. I asked him why, if they hadn’t been together since November, did she still care about what he was doing and who he was with? It made no sense! A nagging feeling in my gut told me that he had just shown his hand. I had always said to him that even though we had a totally fucked up “relationship,” that I was happy that at least he had never cheated on me. At least I had that to brag about. Little did I know how wrong I was…

Two days later I sat down to write an email to Harry’s ex. I knew deep down that something had or was still going on that I didn’t know about. I wanted the truth and I knew that I wasn’t going to get it from Harry. I spent 20 minutes looking at my screen and going back and forth trying to figure out if I should send the message. I finally hit send. Immediately I noticed that I had an email in my Facebook mail folder, the one for people who aren’t “friends” with you. My jaw dropped when I saw that Harry’s ex had sent me an e-mail 20 minutes earlier. 5 hours and a box of tissues later I finally had all (or so I thought) the information that I needed. Harry had been sleeping with his ex on and off during our relationship. Interestingly enough, the only break they had taken were from March through May, which were our best three months. The weekend after Harry broke up with me after our week long official relationship, he was sleeping with her again. I hated him. I didn’t even want to confront him because of how defeated I felt. I let his ex text him and tell him that her and I had spoken and that she had told me everything. Harry went into damage control mode and began texting me, telling me that she never meant anything to him, that it was just sex. He told me that I was the only person who meant anything to him and that I was his best friend. He said he was going to tell me, that he wanted to tell me, but he had been afraid of losing me. I didn’t want to hear it. I didn’t care. I was mortified. The whole time I had thought I had been special, but I was really just like everyone else who had come before me. He had fooled me the same way he had fooled them all. It was crushing to realize what a naïve sucker I had been for so long. I found out later on that it wasn’t just her. He had slept with several other women during our time together. For all of my love, faithfulness, and loyalty, all I had gotten in return from Harry was public humiliation, a 5 pound weight loss (can’t really be mad about that, I suppose), and an appointment to go get tested. Clean, thank god!

Moral of the story – don’t ever believe a man who quotes romantic movies to you. In fact, don’t ever trust a man who watches romantic movies period. They’re just gathering material to use on their next victim. But whatever, I’m totally cool now. It’s not like Harry fucked me up emotionally or anything. It’s not like I’m at all bitter or resentful…


Harry wrote me a heartfelt email explaining a lot of things to me and telling me how important I was to him. As much as I wanted to be strong and cut him out of my life, inevitably I missed my best friend. Harry eventually wormed his way back into my life, although admittedly, I didn’t make it very hard for him. This time, however, it is strictly platonic. I couldn’t and didn’t want to live without my best friend, but I definitely wanted to live without the constant heartache and the ups and downs that go along with having a relationship with Harry. So we are still best friends, and I still probably do more for him than I should do, and I’m still a sucker when it comes to him, but I no longer live with the foolish belief that Harry and I will ever be anything more than what we are. In fact, as I write this article today, Harry currently has a girlfriend! That’s right; he is in a bona fide relationship, WITH labels! Turns out that he could, in fact, be with someone! That someone just wasn’t me. But truth be told, after having been put through the ringer time and time again, I don’t have it in me to be anything more than Harry’s friend. It seems he has found the ability to make it work with someone else, at least for now. And after having loved Harry for longer than I probably should have and after having ridden the Harry rollercoaster for nearly a year, I can finally and truthfully say – better her than me.

Oh, and I’m still friends with Harry’s ex 🙂 Good friends! We’ve got our own little support group going on…and we’re saving a seat for you girl!! Ba dum bum.


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2 thoughts on “When Harry Met Sally…and Kathy, and Sarah, and Rebecca, and…

  1. Your stories are engaging, humorous, well-written, and often insightful. But I’ll be blunt; I’m left with a question—what is the ultimate goal for you? It’s implied that a long term partner is what you’re after, but your decisions don’t seem to reflect that.

    When I look at the sum-total of your posts, my impression is that you’re intelligent, likely at least somewhat professionally accomplished, and probably physically appealing. But I’m also left thinking that you haven’t moved beyond sophomore year of college in terms of how you approach your romantic life. Passion and intensity are terrific, but they have a remarkably small impact on the success of long term relationships. Based on the choices you’re making, and even on some of the criteria you described in an earlier post regarding whether or not to swipe right, or the 6’s who you perceive to be acting as 10’s because they’re the best of the leftovers, you place little value on the character traits that may actually make things work over the long haul.

    Clearly, you’re easy prey for cads. Hardly a shocker as they tend to be good at short term excitement. Harry’s an obvious case, as was the character being played by Kevin the catfish. As well, decent, but immature guys will probably be happy to be with you for a while, but will move on when they’re ready for something that requires deep emotional commitment.

    If a decent (read: fit/attractive, successful/financially independent, mature, kind, caring, etc.) guy around your age were interested in you for long term potential , but was directed to this post, I have little doubt that he would run. Based on the description you provide, Harry is basically sleazy and seriously lacking in empathy–maybe even a bit psychopathic in his recklessness with regards to the emotions of the women he’s with. Yet you remain drawn to him. That ain’t maturity.

    If a guy wants something short-term, passionate, and relatively light on real emotional commitment then you’ll be his choice. But if he’s ready to settle down? Not so much.

    So we get back to my initial query; what is it that you really want? If you you want is passion and intensity above all else, then expect to have short, but quite possibly satisfying relationships. They may become more sporadic with age, but that’s not necessarily a bad thing. Lots of people are quite happy with this sort of a lifestyle, and who would anyone be to judge that? If it works, it works.

    But if you what you want is a long term partner to grow old with then I think you have a lot of growing up to do. Character begets character, and if you come up a bit short in that department whilst seeking a long term partner then you end up sleeping with Harry and hoping he’ll stay (he won’t, with you or with the next one). Develop it, and the good ones will be drawn to you.

    1. First, Ouch!
      Second, perhaps the whole point of this blog is for me to put my shit down on paper and be forced to look at in and face it square on. I’ve made some bad decisions but I’m also not the sum of my choices. By reflecting on my experiences I can only hope to learn more about myself and to grow.

      I’m also anonymous so they future potential boyfriends can’t find this and run away 🙂

      What do I want? I want it all, like most people. Passion and good character shouldn’t have to be mutually exclusive. But maybe I’m really just a dreamer. I guess we will find out. I’ve nailed some good quality men down before, I’m certain that I will be able to secure myself a good, mature, and well rounded guy when he happens to come along. Until then, I can only write what I know and what I think. If it makes me come off as shallow and immature, I guess I need to own that. But I also know that I’m a lot more than that. I hope that helps to clear things up. I do appreciate your feeback, however, and respect your opinion even though I disagree a bit. Especially the part about being capable of deep emotional connections. In my eyes, that’s perhaps my biggest downfall. I crave emotional connection and value it above all else and I am very capable of connecting on a deep level. But I have a hard time finding men who are looking for that level of commitment and attachment.

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