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Help Him Ask You Out!

You meet, hit it off, and then… nothing. What gives? Here’s why men flirt and run, plus ways to make sure he seals the deal.

By Mary Kate Frank

he other night, I had a great talk with a cute guy at a party. It was more than a great talk, actually. It was standing together in the kitchen for an hour, asking each other getting-to-know-you questions (Where did you grow up? Who’s your favorite Beastie Boy?) and joking around (He mocked my admittedly giant purse). It felt like the beginning of something. Visions of a shared future danced in my head. “It all started when he made fun of my giant purse,” I imagined telling my friends. And then, suddenly, Mr. Oh-So Promising was gone.

Yep, he left. He said a quick goodnight, put on his coat, and bolted. No exchanging numbers or
More than one of my friends had also been the victim of Chemistry-and-Run.
email addresses. No “Wanna grab a latte next week?”

When I related the story to my girlfriends, they empathized. More than one of them had also been victims of Chemistry-and-Run. So, on behalf of confused women everywhere, I consulted Jennifer Oikle, Ph.D., a dating coach at Coupling Connection in Denver, CO, for advice on how to decode — and deter — this baffling male behavior.

Possibility #1: He’s Not Sure You’re Into Him
You giggled at his corny jokes! And feigned interest in the playoff prospects of the Red Sox! How could he not know you’re dying to spend more time with him? Never overestimate the power of male intuition, advises Oikle. “There are lots of guys out there who lack confidence and won’t ask you out unless they’re 90 percent sure you’ll say yes,” she says.

The Fix: Give him a compliment he can’t miss like, “That shirt looks great on you.” Or use that tried-and-true move: the lingering gaze. It worked for New York City dater Kari Neering, 30. When a guy she’d been chatting up at a bar didn’t make a move at the end of the night, she looked deeply into his eyes as they parted ways. He got the hint, and they exchanged digits. “Had we not shared that long stare, it’s entirely possible that I could have left the bar before he had the guts to get my number,” she says.

Possibility #2: He Has No Idea How To Ask You Out
While clubbing with friends, Rosanna LaRocca of Bergenfield, NJ, caught the attention of the cute DJ. “While addressing the crowd, he pointed me out, complimented my outfit, and said I was cute,” the 25-year-old recalls. He later found her on the dance floor, and they had a great conversation. But without the mic in his hand, the DJ seemed unsure of how to proceed. He disappeared instead. “Why would you take 30 minutes out of your night to
“A lot of guys won’t ask you out unless they’re 90% certain you’ll say yes.”
whisk a girl off her feet if you’re not going to do anything about it?” sighs Rosanna. He’s likely clueless about how to actually ask you out, says Oikle, or what you might want to do on a date.

The Fix: Make it easy for the guy: Drop a big hint like, “Have you heard if (fill in the name of new blockbuster action flick here) is any good? I was thinking of going this weekend,” or “I’ve had an urge to play miniature golf lately. Know of any places nearby?” If he’s interested, he’ll run with it.

Possibility #3: He’s Intimidated by You
He’s a struggling grad student who subsists on cereal and ramen noodles; you have a Big Girl job with your own fax number. Or maybe he’s super-reserved while you’re the life of the party. Whatever the reason, if a guy suspects he’s less important/cool/worldly than you, he probably won’t step up. “Even when he looks confident, most guys have delicate egos because our society instills in them a need for achievement,” says Oikle. “So when you appear more successful than him, in any area, it can make him feel insecure, like less of a man. Dating is about asserting his masculinity. If that’s in doubt, he’s gonna run.”

The Fix: You don’t care about surface stuff like whether he owns or rents, or what income bracket he falls into. You can’t blurt that out, but you can let him know that you think he’s fascinating. Ask him about one thing he’s definitely an expert on: himself! When a shy guy hesitated to ask her out, Bethany Nolan, 32, of Bloomington, IN, coaxed him along by keeping him talking. She asked him about his job, hobbies, sports, whatever. “I expressed plenty of interest in whatever he had to say,” she says. “And I wasn’t being fake. I did want to know more about him.” Her “I like you” signals worked and — one year later — her now-boyfriend is grateful that she made the extra effort!


Mary Kate Frank’s work appears in the Random House anthology Twentysomething Essays by Twentysomething Writers. Her favorite Beastie Boy is definitely Adrock.
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