Lessons from dating the ones that don't fit

Square Peg in Round Hole

When it comes to the dating game, it may be a pretty safe to assume that most of us have our own opinions about what we'd like them to have: looks, job, sense of humor, great style, baggage-free... Yes, a laundry list of "qualities" that when pulled together will make up what we believe is our perfect fit.

However, when it turns out that they're not so perfect, then what?

Of course, the best answer is cut all ties -- you're done.

But then you see them one night, or get a text, a call... And suddenly it seems great again. Tempting, even. Suddenly, you have no idea how or why you let things end. So much so you're entertaining the idea of going down that road again... What to do?

I found myself thinking about that just this weekend, as I was talking to my social partner-in-crime, Marisol*. Anyway, as I was telling her about some of the old boyfriends that I'd let resurface in my life, I also talked about how I planned to finally cut all these exes off  -- something that has always been hard for me to do. Especially when they happen to have eyes, smile and hair that just... Well, we won't go there now.

In any event, even though I'd made the resolution to keep them at bay, I found myself wondering what the allure was of an old boyfriend, anyway. What's so appealing about them that I find myself falling into the same trap?

Even though I still learn a lot about revisiting my past, there are some things I would say were true about why I did it:

  • Filling the Gap: Truth was, I liked knowing that I had a "go to." While I don't have qualms about being single, there are moments when it feels nice to have temporary companionship.
  • Comfort in What I Know: Sometimes, I like knowing what to expect. And, with guys I've been involved with in the past, there were no surprises. I knew what was coming and I was able to manage my own expectations, while not getting too invested. Seems like a perfect way to avoid a little heartbreak with someone new.
  • Glorifying the Past: High school is an irritating part of people's lives. Yet, when they're out, they remember all the wonderful fun they had, ignoring things like glasses, zits, braces and cliques. It's kind of the same thing with an ex. When you're with them, you remember all the things that you hate about them. But, after some time's passed, all you can remember is how great the sex was. Sure, it comes crashing back when you're involved again. But usually, it's easy to remember things the way we want to, first.

These days, I do little things like put IGNORE in front of their names so it's a constant reminder not to pick up the phone, or not stay friends with them on popular social networking channels so I'm not OCD and checking their page. Small steps, yes, and not permanent fixes, but a pretty solid start.

Besides, with the summer in full swing, I'm thinking that the beautiful Chicago weather and plenty of festivals and parties open up a whole new playing field. I'm certainly willing to entertain it. Who knows what the season will bring? And I'll need to make room for the man that ultimately steals my heart.



Leave a comment
  • Let's keep it real. The only two qualities that matter: money and morals.

  • In reply to jenmcautry:

    Interesting thought. Morals are important I agree, and I don't disagree that money (or rather at least stability in income) can hold value, but they aren't the only ones for all people. What brings you to only these two?

  • In reply to jenmcautry:

    If a man doesn't have money, he's a bum. If he can't be trusted, he's a bum. Good looks? Nice but not essential. Sense of humor? I don't need a comedian. Organized? I'm not. Helpful around the house? If he has money I can hire a housekeeper. Emotionally stable? Everybody's a little crazy. I mean no Drew Peterson/R. Kelly/Charlie Sheen kind of crazy or substance abuser crazy, etc. Clean? Hmmm. OK. I'll give you clean.

  • In reply to jenmcautry:

    I guess the bottom line here is that everyone has their preferences! And if it works for you, then go with it.

Leave a comment