Dear Wendy: “Is It OK To Email A Former Online Match?”

I’m currently single, but have been active on a couple of online dating sites for a couple of years. I’m not looking for random hookups, but an actual meaningful relationship. Clearly, I’ve yet to find that, although I have met/e-mailed with some extremely decent guys. Last winter I was e-mailing with this guy I was very interested in — we never talked on the phone, but we exchanged long emails, and I really felt like we connected, that we shared a lot of interests and the same sense of humor. We were talking about meeting up for drinks, but it was hard because we were both visiting family over the holidays. Then he met someone else and sent me an e-mail explaining why he hadn’t responded, telling me he wanted to keep in touch and apologizing for potentially being a d-bag. We never did meet up, but through some internet stalking I found out he ended up in a relationship with that someone else, but I think he may be single again. I know, I sound like Glenn Close in “Fatal Attraction” right now, but if it means anything, I never spent more than a few minutes looking him up. My question is this: would it be overly creepy/internet stalker of me to e-mail him now, a year after we stopped talking? He keeps coming up in my e-mail matches, and I was so excited to meet up with him before he met someone else. Also, I’m starting to get really tired of looking for decent men online, especially knowing he and I probably have a high chance of hitting it off in person. Should I shoot him a quick message or just leave it in the past? — Still Interested

Yes, by all means shoot the guy a quick note. If he’s showing up in your email matches, that means he’s back on the scene, and I don’t see any reason why you shouldn’t reach out and see if you can pick things up where you left them off a year ago. I’ll caution you, however, that if he is popping up in your email matches, you’re probably popping up in his, and if he hasn’t contacted you yet, there’s probably a reason. He may feel embarrassed about the way he left things (blowing you off for someone else, basically), or perhaps he was never as interested in you as you were in him. But as long as you’re realistic about your expectations and keep your email brief and friendly (“Hey, you’ve been popping up in my matches. I had such a nice time getting to know you over email last year. How have been?”), there’s nothing at all creepy about trying to reconnect with someone who could be a potential match, especially considering how difficult finding a “decent man” can sometimes seem.

I have been single for some time now and have been running into a problem in my search for a potential mate. We have all read the advice that men don’t like women who are too easy to get and aren’t a challenge but I can’t stand playing stupid head games. If I find someone interesting I would rather call him and set up a date rather than wait around for him to call. To do those kinds of things feels completely unnatural to me. Clearly what I’m doing isn’t working the way I would like because more often than not men lose interest quickly and move on. How can I stay true to myself without chasing men away with my over-eagerness? — No Games

Have you considered that perhaps it isn’t the way you pursue men that’s the issue, but the men you choose to pursue? For the next few weeks, why don’t you try a little experiment: Rather than going for the kind of guy you typically go after, turn your attention to the guy you wouldn’t normally find yourself pursuing. If you normally go for the “hot” guy, the one who’s gregarious or super charming, check out the quiet, shy guy instead. Maybe his appearance isn’t as immediately stunning as the hottie you normally chase. Maybe his jokes don’t come as quickly. But here’s the thing, if you pursue a diamond in the rough, rather than the guy every other woman is lusting after, you’ll probably find your chances are way better. Not only is there less competition for guys like that, but they’re more willing to put in the work to keep you around and they’re appreciative of your attention. If you’re lucky, you may find that by giving those kinds of guys a chance, you end up with a real winner — someone who’s a long-term match, rather than a one-night stand just looking to add another notch to his bedpost.

*Do you have a relationship/dating question I can help with? Send me your letters at [email protected]