Anna Pulley, @annapulley
RedEye's sex columnist
3:09 PM CST, February 15, 2012
I started casually dating a guy about two months ago. We've been on half a dozen dates, and I like him. We're very sexually compatible (haven't slept together yet but have done everything but), but I'm still not 100 percent sure if there's anything long-term in our future. Last week, a friend of a friend and I hooked up at a party, and now he's asking me out on a date, and I'd like to go out with him to find out if we're compatible. So now I find myself dating and hooking up with two men simultaneously. This is the first time I've done this, and I feel like it's a bit awkward. Is it totally OK to do this? Do I need to tell the guy I've been seeing longer about this new man? How do I handle this without it winding up like a really awful romantic comedy where I book two dates on one night?
—It Takes Two
Wait, I know this one. I saw it on a "Sex and the City" re-run. You double dip, but decide you like the first guy better, so you tell the second guy you're sick, only he decides to be sweet and bring you soup just as the first guy is kissing you goodnight! Then they both dump you simultaneously and split a cab back to the Upper West Side in a way that is vaguely homoerotic. Thankfully, you get a new boyfriend in the next episode; otherwise this would all be really depressing.
To put it in less sitcom-y terms, you have my hearty approval to date two dudes at once. In fact, it's practically a rite of passage these days, especially if you're a U.S. senator. Anyone who's ever been to a dueling-banjos night will tell you when it comes to teeth, four is all you really need. Wait, no, it's that two is always better than one. The same logic applies to casual dating, and here's why:
It lowers the pressure for all of you. We all know from reading Cosmo that guys—like horses and small children—spook easily, so the best way to avoid scaring them off is to not be way too into any one person too soon.
Less pressure is good, especially in casual situations when you're on the fence about someone, as you seem to be with guy No. 1. It's easier to discern what you want when you have more than one option in front of you. Why else would the Hometown Buffet franchise thrive? It's not the creamed corn surprise, I tell you.
Also, it's dating, not, like, signing a 30-year mortgage. There's no need to be exclusive while you're getting to know people. Besides, unless you have that "let's go steady" talk over malted vodkas, the assumption is that you're dating around. I do think that honesty is important in scenarios like this, especially if you're sleeping with more than one person (more on ethical sluttery here). This doesn't have to be some big confession, unless guy No. 2 is guy No.1's brother or you're on "The Real Housewives of Cook County" or something.
In regards to fear of double booking, dating more than one person shouldn't be any more challenging than having access to a day planner. If you have the wherewithal to schedule both a dentist AND a gyno appointment in the same week, you'll be fine.
Want to ask Anna an anonymous question about love, sex or dating? Email your quandary to firstname.lastname@example.org.
Need to give your dating life a boost? Sign up for RedEye Dating. Pick dates, not people.
Copyright © 2013 Chicago Tribune Company, LLC