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New Ways To Ask Someone Out


Stuck for a fresh way to invite someone cute out on a date? Here, some original approaches that will up the odds you’ll hear a “yes!”

By Amy Spencer

t seems so simple: If you like someone, and you want to take him or her out on a date, you just ask, right? Well, we all know that it’s much harder than it looks—which is why most of us clam up, bow out, fidget, mumble and fumble at the moment of truth. But those days can soon be history. The key? Take your mind off the possibility of rejection by adding a little life to your next invitation. Here are ways to ask someone out that are so new, different, and unexpected that your askee will just have to accept!

Ask your intended out on paper…or a paper napkin
If you’re out at a bar and notice a cute person standing there, put the cocktail napkins to good use. Remember those grade school “Do you like me?” notes you used to pass
Go to Evite.com and arrange a small party… so small that the only invitees are you and your date.
around? Do something similar. Grab a pen, write down, “Would you like to go out next week?” with a “Yes” box and a “No” box beneath it. Fold up the napkin note and pass it to him or her with the pen.

Pull your own “To Be Continued…” episode
The less you know the person you’re asking out, the better off you are with this technique. While no one is suggesting you ask out a total stranger of course (for safety’s sake), this is a good approach if you’re attracted to a friend of a friend when, say, you’re all out at a bar or party. Start a story, then stop partway through saying, “Oh, this is a two-part episode. To hear the other half, you’ll have to tune into a date with me.” Why do I know this works? Because a guy I met in a bar used something similar on me a few months ago. We’d been talking about traveling adventures we’d had, and he said, “I have two funny stories about that.” After finishing his first story, he said, “As for the second story… well, I’ll tell you when we go out for dinner.” We’ve been out for four dinners since!

Hire a stand-in to do the asking
If you’re feeling too chicken to approach the gorgeous stranger across the room, have a friend — or the party host, or the bartender at your favorite hangout — do it for you. Ask them to say to your would-be date, “My friend over there wants to know if you’ll go out with him/her.” Then be sure they pour on the charm for you with glowing lines, like, “She’s a great woman, and you’d be a fool not to go out with her.” Or “I mean, he’s a cool dude—check out his shoes.” Once you have the object of your affections smiling, then you can move in for the answer personally.

Evite someone for a one-on-one
If you already have the email address of the person you want to ask out, let an Internet invite do the talking. Go to Evite.com and arrange a
Ask your intended, “Let’s play pool. If I win, you take me out. And if you win, I’ll let you take me out.” Let the game begin!
small party… so small that the only invitees are you and your date. In the reply box, you, of course, should write something funny like, “Heck yeah, I’ll be there! Count me in!”

Sneak it onto their to-do list
If someone you know (and like) hasn’t gotten around to asking you out — and if you’re the bold type — insert it into their schedule. Yvi Chen, 30, penned this approach not too long ago. She was at a friend’s house (a single, handsome friend’s house) and wrote in his calendar, “Call Yvi to remind her about having dinner next week.” On the next page, a week later, she scheduled in, “Dinner with Yvi.” Yes, it was cheeky, but she felt she had nothing to lose. “I knew he’d either call to comment on what I wrote in his calendar, or he’d just pretend he never saw it,” says Yvi. “I was fine either way. I just didn’t want to be rejected face-to-face.” As if. In the end, Yvi got the “remind,” and they dined!

Start your own rumor
If there’s someone you’ve been flirting with for a few weeks or years, and you can’t figure out a way to break the “friend” boundary, here’s a plan that can work brilliantly. Tell the person you have your eye on, “So the rumor is, you want to ask me out…” If he really does want to ask you out, you’ve just handed him a safety net for rejection. And if he hadn’t thought of asking you out, he might be intrigued enough by the “rumor” to look at you in a new light. If he says, “Who started that rumor?” Say, “I can’t reveal my sources.” Or “I can’t tell you who, but it was someone very smart.” My friend Lisa tried this with a guy she’d been flirty friends with in college who’d never made a move. Though he was flustered for a minute, she finally said, “Look, are you going to ask me out or not?” He said, “Uh… yes.” She then said “yes” to a date that night. And five years later, she said “yes” to his marriage proposal.

Make a wager
The next time you want to ask out a stranger you meet at a bar or party, up your chances of getting a yes by upping the fun ante. Say to him or her, “I’ll play you in a game of pool. If I win, you take me out. And if you win, I’ll let you take me out.” Let the game begin!

Be specific and straight-up
Whether you want to ask out a stranger, a friend or someone you’ve struck up a conversation with at a party, go bold. Replace a wishy-washy line like, “So yeah, we should hang out or something soon, you know?” with a far more straightforward, “Would you like to get sushi with me next Thursday night?” No mixed messages, no fumbling for words, and oozing with confidence… and that’s something every date askee wants to hear.


Amy Spencer writes for Cosmopolitan, Real Simple, and other publications.
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