How to Ask Him Out Without Him Knowing It

Sick of waiting to be swept off your feet like the heroine of a Victorian novel? Quit playing hard to get and take control of your dating destiny (you know, without being scary)
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How to Ask Him Out Without Him Knowing It

Sick of waiting to be swept off your feet like the heroine of a Victorian novel? Quit playing hard to get and take control of your dating destiny (you know, without being scary-aggressive).

-Angelica Catalano, YouBeauty.com

couple at bar laughing

Seinfeld fans may recall an episode where a guy makes ridiculous bets with Elaine (“Dustin Hoffman was in i”). His intention: To purposefully lose and have to buy Elaine dinner. This artful scheme of asking someone out without them knowing it sounds like the stuff of fiction, but it happens more than you think.

Emily Neimanis, an associate producer in Rochester, NY was once tricked into having a date when she was a junior in high school. “I thought it would be a normal Saturday night hangout with many people. But when we got there it was a total set-up,” she says.

There was only one other couple there. “I was of course confused, but it turned even more ‘datey’ when we all went into the basement (lights off) and watched a movie.” Classic.

The best part: The other couple left Emily alone with the guy. It worked, though—Emily ended up dating him for two years.

Read What’s Your Magic Sex Number?

Sneaky dates happen well past high school. YouBeauty reader Margot shares, “I reconnected with my old high school chem lab partner after 10 years at our reunion this summer, and he invited me out to a hockey game,” Margot says. “I thought we were going with friends… but he ended up asking if I wanted to get dinner with him after. It was like an ambush date!” At first, it seemed like his approach didn’t work. But Margot and he began growing a relationship, and are still together today.

Ambush-dating someone doesn’t have to be awkward. Admit it: At some point, you’ve wanted to ask a guy out but couldn’t muster up the nerve because either you were afraid you’d come off sounding like a spaz, or you were scared of rejection (or both).

First off, you may be met with shrieks of horror when you confide in your friends and family that you’re going to ask a guy out. And it’s not just your old-fashioned mom who insists you assume the conventional role of “the pursued.” It’s also your forward-thinking friend who lives by the “He’s Just Not That Into You” logic: A guy will chase you if he really wants to see you. But in reality, this isn’t always the case, according to YouBeauty Relationship Expert David Sbarra, Ph.D. A man may not initiate, even if he really wants to get to know you.

“Men don’t ask women out for all kinds of reasons that have nothing to do with interest level—they’re shy, scared, self-conscious, et cetera,” Sbarra says.

Before swearing off a man who doesn’t step up right away, consider this: He might not want to be forward and “overstep his boundaries.”


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