“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: