Dating Don’ts: How To Deal With The Ambiguous Dater

Every woman I know has been in this situation at one time or another, wondering whether the guy she’s wasting—I mean, spending most of her time with is interested in her as a girlfriend or just a buddy.

In my case, his name was Daniel. He’d flirt, drive me around in his cool vintage car, and generally make me feel like the coolest, prettiest, most fun girl in the world. We hung out 24/7. He was like my boyfriend, except he never made a move. Ever.

Ambiguous boys don’t want to go on dates—they want to “hang out.” They don’t want to be labeled your boyfriend—or even the guy you’re seeing—but they want all the “perks” that are generally part of such an arrangement.

I’ve never been one to play it cool, so my ginormous crush stank up every room we entered. I was too shy to actually articulate my feelings, but I eventually figured out that while he genuinely liked me, mostly he was using me for ego gratification while he pursued other women he actually wanted to get physical with. Things came to a head one night when I ran into Daniel while I was out at a bar with a spectacularly handsome, much younger French dude.

Predictably, seeing me out with someone much prettier than either he or I ignited a fire under Daniel’s non-committal butt. He grabbed me on my way to the bathroom and cornered me like he was going to kiss me. A week prior, I would’ve been in heaven. But this night, I was with someone who was not only into me, he was unapologetic about saying so. I shoved Daniel away, hissing that he’d had his chance and the only reason he wanted me now was because I was no longer available for ego-feedings. He gulped and looked ashamed. That was the last time I put up with an ambiguous boy.

But their numbers are legion. Ambiguous boys don’t want to go on dates. They want to “hang out.” They don’t want to be labeled your boyfriend—or even the guy you’re seeing—but they want all the “perks” that are generally part of such an arrangement. I’m not talking about friends with benefits here; that’s a whole other animal. What I’m talking about is the frustrating purgatorial gap between friend and boyfriend.

“We call it hanging out so as to avoid date rejection,” said one twentysomething record producer I interviewed. Jeff, a 28-year-old bartender I spoke with had another take. Claiming he hasn’t had a “date” since his high school prom (although he’s had plenty of girlfriends), Jeff’s theory is that “ladies love to talk and communicate things and guys by nature do not want commitment. So the longer you ignore labeling it, the longer you are in the clear to see other girls without the guilt or remorse of feeling like a dirtbag.”

My friend Jess, a sexy young librarian-in-training has no patience for this kind of gray-dating. She says, “I usually just force their intentions out of them,” but she warns that only works on guys who like aggressive ladies. “I have actually said, ‘Is this a date?’ And then when he inevitably pauses, I add, ‘and by the way, whether or not we hook up later may hinge on your reply.’”

But perhaps the best advice came from yoga teacher Lily, who believes an ambiguous dating situation is best handled using reverse psychology. Though she hasn’t yet had the opportunity to road-test her theory, she advises, “Anytime your non-boyfriend asks you for a favor—like to put his phone in your purse, or get him his beer while he goes to the little boy’s room — scream: ‘I’m not your freaking girlfriend! Do it yourself!’”