Getting Around Town With Jamie Shupak: On the Virtues of Dating Around

Getting Around Town With Jamie Shupak: On the Virtues of Dating Around

On September 26th my boyfriend and I will celebrate our first anniversary. We settled on this date while trying to pinpoint exactly when we got together. He didn’t officially ask me to be his girlfriend until early November, but this particular night was when something changed between us. Well, for me at least.

 

Seeing other people is one of the best ways to make it work with a woman you're interested in.

 

He says he “knew” how he felt months earlier, but even though he “knew,” he still went on two dates with other girls after September 26th. He jokingly calls those other dates “meetings."

(No, I did not take any “meetings” after September 26th last year. Nor am I going to take any “meetings” this weekend. Or ever.)

I call what he did slutting around; he calls it hedging his bets.

I joke that his “meetings” offended me, but they’re nothing other than a good laugh and an even better story now.

As long as no promises are made, neither person thinks there’s anything exclusive going on, and no one’s feelings get hurt, I see nothing wrong with keeping a full Rolodex. (He’s going to love reading this!) There are so many benefits to dating more than one person at the same time.

Seeing other people is one of the best ways to make it work with a woman you're interested in. Sounds counter-intuitive, but I promise it works. (I mean, I did it for my boyfriend!) It keeps you from trying too hard, scaring her off with all of your energy and enthusiasms. This way you don’t have to pretend you have other commitments and things going on—you actually do. We want you to be social and have fun. We want interesting things to happen in your life.

This will also keep you from contacting her too often. No woman wants to be smothered by a guy. Some attention, some affection, yes, but too much and she’ll start thinking you’re desperate. It might seem crazy, but your stock goes up a little—sometimes a lot—if we think other women want you.

Spread your love—and time—around to different women and it’s less likely that one name in your text queue or Gchat list will drive you crazy.

It’s a way of simultaneously playing hard to get and protecting yourself. Aren’t you less likely to feel burned and rejected if you have another woman to call? Nothing says, “Whatever, girl, I’m cool,” like having other options. Holding onto a full deck also improves your odds on any given night. I’m not just talking about hooking up, you're more likely to have good nights, have opportunities to meet other people, and have plenty backups for when other plans fall through.

Perhaps most important of all, dating around gives you practice. Again, not just in a physical sense, but practice at dating, at being a good partner. Like any sport, it takes doing it over and over to get good. I tell my single friends this all the time—the ones who make out or sleep with someone too soon—that they’ll be less likely to make those mistakes if they had dated more people, more often. The more women in your arsenal, the less tempted you’ll be to pounce on one of them, because you know you have other chances.

It’s not just learning how to act on a date—where to go, what to say, what to wear—but also how to handle the time between seeing each other. When to text, how often to email or call, and how forward you should be are all skills that require honing.

Again, I only endorse this behavior if you are casually dating. If you really like one of these women and see a potential future with her, then continue at your own risk. She might not realize how much she likes you yet, as was the case with me last September. And once she does come around, you don’t want her to resent you for spreading your seeds around so generously, so to speak. Feelings can—and often do—creep up without much notice. So, look out for things like her initiating the plan-making, or responding to your emails and calls sooner and with more feeling. And be sensitive to the fact that all this fun could come back to haunt you.

In the meantime, remember that dating is a numbers game. The more women you meet, the more women you go out with, the better your chances are of finding one that you like and want to date seriously.

If that kind of math is more your speed than counting days and months until an anniversary, then keep spinning that Rolodex.

In Two Weeks: y u should txt like an adult

Tags: jamie-shupak, getting-around-town-with-jamie-shupak, dating, dating-advice
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