If your ex was a jackass the first time around, he probably still is

Excerpted from
The Spinsterlicious Life: 20 Life Lessons For Living Happily Single and Child-free
By Eleanore Wells

The success of a revisited relationship depends on why you broke up the first time. It could be a good idea if the reason for the break-up was situational, that is, if there was something going on in your life or his life that got in the way of the relationship (e.g., work, school, distance, immaturity) and that situation has been resolved. However, if the reason for the break-up was personality-related, don't waste your time. He's just like he was before... only older.

Not too long ago, I reconnected with a guy I had dated 15 years earlier. The first time around was interesting -in a peculiar kind of way. If I had been serious about guys, I never would have gone out with him. He was charming, but also known to be a little slippery; however, I didn't want to get married so I could just have fun dating him without having to consider where this could go. This relationship was perfect for that mode of thinking. I liked him, even though I never really penetrated the surface. For the most part, our interactions in the second year were just as superficial as they were in the second month. Neither of us knew how many siblings the other had, each other's birthdays, or lots of other things you'd imagine friends just know about each other. We played totally in the moment. But he was fun, so from time to time over the years after it ended, I wondered if he could have been The One if our relationship had been different (even if I was never really sure what The One meant for me). It was a provocative notion, based on not much at all.

Given that our relationship was spontaneous and not at all deep, there was no real reason to imagine there should have been more, but I think I was just really curious about what was beneath the surface. I wondered if it would have turned out differently - more favorably - if we had done things differently. So I decided to find out what would happen if I agreed to a do over.

I'd always found him intriguing. He wasn't physically attractive (one of my friends thought he looked like a camel), but he was really smart, and funny as hell. He was far from perfect, but I didn't mind at all because (1) so was I, and (2) how boring would that be? I've always preferred to err on the side of rogue.

We weren't serious, so we weren't monogamous. We had what could be called a "don't ask, don't tell" policy that we never even discussed; we just understood. My reason was because, though I liked him a lot, there was always a void there that I looked to others to fill. I imagine he had his reasons.

When we were finally done with each other the first time, it ended quietly. There was no big blowup; I was angry and hurt, but just kinda sucked it up. We didn't even talk about it. He had behaved badly and was cowardly about it. We (okay, I) simply stopped speaking because it was just too preposterous to even discuss.

Here's what happened: he had a baby and somehow neglected to mention it to me until she was about six months old. (Actually, he had two, but I'll get to that). Now, because we were both seeing other people, I do understand how this could happen. I'm pretty sure, though, that he was still supposed to mention to me that he impregnated someone and would soon be a father. In fact, he probably should have told me, say, six months before the baby was born, not six months after. So, that ended that. He had a new family to tend to and I wasn't speaking to him, anyway. I was pissed that he hadn't been upfront about this whole scenario.

Within a year or so, he started to reappear. He thought we could pick up where we left off. I wasn't sure this was a good idea but babies do happen sometimes and the parents don't always work it out. I must not have been very busy with anyone important at that moment, and I did have to do some mental gymnastics to make his spinelessness okay. He worked hard at trying to talk me into why we should start seeing each other again. Then, before I could get to "yes", he got the same chick pregnant a second time! Yep. It happened while he was trying to convince me to give him another try, and again he was too chickenshit to tell me. I heard about it from a friend.

After that, I didn't speak to him for years, though I ran into him often. Our circle of friends overlapped a bit, so I couldn't avoid seeing him. At first, my stomach would hurt, but soon I didn't really care. I felt kind of sorry for him. I mean, really, who has two kids "by accident?" Nevertheless, over the years, more than one friend would occasionally urge me to reconsider him. He, too, put in quite an effort at this. He even started getting his hair cut at the barber shop a half block from my apartment, even though we lived nowhere near each other... and he's bald. He did this either to catch a glimpse of me or to aggravate me - possibly a little of both. The very thought of reconciling was mostly laughable to me, though sometimes when I was between relationships I'd remember his charm and ponder "what if."

History books, pop culture, and the wedding section of many newspapers are rife with stories with happy endings from relationships revisited. So, why not give it another shot? We were 15 years older, which I chose to interpret as wiser. We were armed with details of what happened the first time around, so we should be able to do better. Plus, surely he was all the things he was before (still smart, still funny) and was presumably smarter about how to have a relationship with me. I certainly considered myself to be better in every way. With all this in our favor, it should go better this time.

I went from thinking of this reconnection as absurd to actually becoming pretty excited about it. And what a nice story it would make! Most of the women I mentioned it to loved the idea. Interestingly, one male friend Mr. X and I had in common was sure that this was not a good idea: "I don't doubt that he wants to do this; I just don't think he can. He doesn't know how". Well that response wasn't exactly the endorsement I was expecting. This would be a romantic story and our friend obviously didn't understand that. Deep down, I was having my own doubts about whether this was more about the fantasy than the reality, but I pushed those doubts away.

So, we agreed to go for Round Two, 15 years later. This is a one-sided tale so I cannot explain why he made such a big effort to woo me back, only to begin to move in v-e-r-r-y-y slow motion as soon as I said "okay." I suggested we see a movie for our first official date, and then I didn't hear from him for two weeks. That was my first clue that this revisited relationship was not a good idea. Perhaps I wasn't wiser after all given that I ignored this bright red flag and did not step away as quickly as I should have. Short story shorter, the relationship didn't go that well the second time around either, for most of the reasons it didn't go well the first time (minus more babies, as far as I know).

One final Saturday night, he called while I was having dinner with a friend to see if I wanted to get together. He was playful and flirtatious and it sounded like fun, so I wrapped up dinner early, called to say "my place or yours" and was stunned when he then said he couldn't really do it because he was busy preparing for his kids the next day. What? At that moment I decided this was just stupid, and I'd had enough. He was twisted in a way that I couldn't understand, which made it really easy to pull the plug right away; maybe I was a bit wiser.

After the excitement I initially felt at giving what-might-have been another shot, I thought I'd feel sad when I ended it. Instead, I just felt relieved. This time I understood, really understood, something I believed after our first break-up but chose to talk myself out of once I decided to go back in: the way he handled the situation 15 years ago said he was pretty messed up back then, too.

So what did I learn? Sometimes the second time around isn't so much better (the opposite of what that song by Shalamar says). Sometimes it's even more ridiculous.