Mostly Mensch: Pursuit

PursuitcolumnpicOnce upon a time, there was a young, idealistic man. During his college days, he met a particularly lovely lady who happened to get a job at same company he already worked for. He was happy to show her around and help her get adjusted and acclimated. There was a genuine friendship toward this woman, regardless of the (distant) hopes of gaining her deeper affection in return. He’d check in occasionally and see how she was doing. An e-mail to see if she needed anything. A stop at her desk for a quick conversation when there was time (he probably found time too often). An offer to buy her a drink when the staff went out after work. Attempts to get her to laugh about college experiences in a professional workplace. After a few weeks of this, a mutual friend and coworker pulled him aside at the request of the object of his affection. She asked him to please stop paying so much attention to this woman as it was making her uncomfortable. The aforementioned young, idealistic man was incredibly embarrassed to have crossed that line and vowed to avoid that experience again.

In what I’m sure is a shock to readers, that young, idealistic man was me. But as I’ve matured—and have the separation necessary to look back (mostly) objectively—I see that as a solidifying life experience; one that’s led to what’s become a favorite phrase of mine when it comes to dating: There’s a fine line between pursuit and stalking.

And the basic problem? Figuring out where the heck that line is. Standing outside the house of your crush playing romantic music, emulating John Cusack and the boombox scene in Say Anything? Some women that I’ve talked to have said they think it’d be romantic. Others would call the cops. I don’t think I’d do that to begin with, but with my luck, I’d do it for the woman who would call the cops. (Although if women like bad boys, could that actually help my dating life??)

What’s romantic for one woman may be too much for another. What would be seen as “storybook” by one may be seen as nauseating by another. Based on discussions that I’ve had, I can definitively say that waving at a woman of interest from across the room is not enough. Sitting outside their residence, waiting for them to come home is too much. Just about everything in between leaves room for interpretation.

Women want to be pursued. I get that. One of the great things about having numerous female friends is that I get to hear all sorts of perspectives, and the desire to be pursued is nearly universal. When I ask for a specific definition of what that means, however, explanations get a bit murky. I’ve been informed that I should never ask for a woman’s number on the first meeting—that I should find creative ways to see them again so I don’t seem overeager. Others tell me to definitely ask, as it shows a strong interest, and strength is good. Some tell me that I should absolutely e-mail or call the day after the first date to let them know that I had a good time. Some tell me that I absolutely shouldn’t because I’ll come off as desperate.

The impression that I maintain from these conversations is that in many cases, women will know “appropriate” pursuit when they see it. Needless to say, it’s a frustrating scenario to face. But the more I think about it, the more I understand it. Especially for those who have never had that “big” love. They don’t necessarily know exactly what it is that will make their head and heart go, “Yep, that’s the one.” (I’m in the same boat there… Is what I think I want what I really want? That’s a discussion for another day…)

But women know that they want to feel needed. And wanted. And appreciated. And worth every bit of effort that it takes for both the man and woman to be sure that this is right.

It still leaves a conundrum for the guy who doesn’t want to make a woman uncomfortable again. I can’t follow all of the well-meaning advice that I’ve been given because I’d wind up a bigger mess of contradictions than I already am. I wonder how many opportunities I‘ve missed because I wasn’t willing to pursue just a little bit more for fear of crossing that line, but I don’t think that there’s a perfect solution for finding that happy medium.

What do you think is crossing the line in pursuit of a love interest? Leave your best (and worst) examples in the comments section.


When Josh Krauskopf isn’t doing his day job, he’s trying to learn new places to focus his creative energies. Improv and writing are the current obsessions, but there’s undoubtedly more to come. He firmly believes that if you’re not learning, you’re dying!