I sensed that this guy was a little, um, high-maintenance from his overuse of ;o) smiley faces, the tone of his emails, and the frequency of his emails. Well, the story didn’t end there. He sent me a follow-up email.

Subject: Hmmmm
Date: 3/14/09

You still around?

:O)

I didn’t respond. I got another.

Subject: Hmmmm
Date: 4/1/09

So correct me if I’m wrong, but didn’t we have SOME kind of dialogue started? Was kinda hoping to continue it, myself… And you?! :o)

Hope you’re doing well…

In fact, I wasn’t hoping to continue it. That’s why I didn’t respond. I know I’m going to sound like a hypocrite (hear me out), but I disagree with his characterization of our email exchange as a “dialogue.” This is the blessing and the curse of online dating: someone can stop communicating as soon as they’re not interested. Sure, I wish more guys on Match would write me back, but they don’t because they don’t consider me a good fit. No harm, no foul. Done. Next. But you can’t take these individual rejections, for lack of a better word, personally. And you shouldn’t be a glutton for punishment.

I wrote him back.

Subject: Hmmmm
Date: 4/1/09

Hi, [his name]–

You seem like a really nice guy and have a lot of good things going on in your life. The more I thought about it, it just didn’t feel like you and I would be a good fit.

Good luck in your search!

Take care,
[My name]

Nothing really to say after that, right? Wrong.

Subject: Hmmmm
Date: 4/1/09

Well, I have to admit that I AM a little disappointed, but I DO understand… And yeah, I am SO beyond the “trying to fit a square peg into a round hole” phase of my life… Been there, done that.

Best of luck to you as well…

Take care,
[His name]

I’m glad I trusted my instincts here and didn’t pursue even another email with this guy. He seems nice, however, if we met up even for coffee, I would regret it about five minutes into it. Plus, I suspect he’d be hard to shake after a break-up.