Ask Him Out Without Him Knowing It

Quit playing hard to get and take control of your dating destiny (without being scary-aggressive).

Seinfeld fans may recall an episode where a guy makes ridiculous bets with Elaine (“Dustin Hoffman was in Star Wars”). 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.

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 – A man may not initiate, even if he really wants to get to know you.

Fortunately, there’s a simple way to make the first move without getting aggressive or into a game-playing tailspin.

No matter how much you know you shouldn’t think you’re asking someone on a date, that date word will be seared in the back of your head.

Here’s the super-chill guide to asking someone out on a non-date:

1) Make it about you, not you two.

Example: I was going to grab some Starbucks later today, would you like to join me?

“In this sentence, I am doing something, and you are joining me,” Sbarra explains.

2) Avoid date-y language. Talking about the two of you sounds the date alarm.

Example: Hey, we should go check out that new Japanese restaurant.

We’re mincing words here, but that’s what makes it the delicate art of asking someone out without them knowing it. Think this sounds too much like game playing? Waiting around and playing hard to get when you want to get to know someone is far more cunning and exhausting.

3) Invite him to do something you’ll already be doing. Simple and light, remember? You’re not going out of the way to plan anything elaborate.

If you cook at the soup kitchen every Sunday, tell him you could use an extra hand. With an afternoon chopping onions, you’ll laugh (and cry!) more than you would on a strained dinner date. By the day’s end, you’ll also know if you even want him to take you on a one-on-one next time.