Way #1: Write an impromptu note on a napkin
If you’re out at a loud nightclub or live music venue 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 around? Do something similar here, but with an adult twist. Grab a pen, write down, “Would you like to go out next week?” with a “Yes” box and a “No” box directly beneath it. Fold up the napkin note and pass it to him or her, along with the pen to write down a response.
Way #2: Pull your own “to be continued…” moment
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, this is a good approach if you’re attracted to a friend of a friend when, say, you’re at a 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 one evening 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 then!
Way #3: Have a stand-in to do the asking for you
If you’re feeling too chicken to approach the gorgeous stranger across the room, have a friend — or the party host, or the manager at your favorite hangout — do it for you. Ask your go-between 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 your proxy pours 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.
Way #4: Use online invitation sites to ask 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 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!” You can also create a two-person event on Facebook and add your crush (assuming you are already connected there, of course!).
Way #5: Add it to his or her paper-based calendar
If someone you know (and like) hasn’t gotten around to asking you out — and if you’re the bold type — write it directly into his or her 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 portable, leather-bound calendar, “Call Yvi to remind her about having dinner next week.” On the next page a week later, she penciled in: “Dinner with Yvi.” Yes, it was risky, 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 sure enough, they romantically dined!
Way #6: Start your own romantic 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 “just friends” boundary, here’s a plan that can work brilliantly. Tell the person you have your eye on, “So the rumor is that you want to ask me out…” If he or she really does want to ask you out, you’ve just handed your rush a safety net for rejection. And if that person hadn’t thought of asking you out, it might make him or her intrigued enough by the “rumor” to look at you in a new light. If the reply is, “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.
Way #7: Make a wager where the winner’s prize involves going on a date (with you!)
The next time you want to ask a stranger out after you meet somewhere randomly, improve your chances of getting a “yes” by upping the fun ante. Say something like, “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 flirting games begin!
Way #8: Be specific and direct by asking someone out yourself
Whether you want to ask out a stranger, a friend or someone you’ve struck up a conversation with at a party, go bold for once. Replace a noncommital 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 be sure to be oozing with confidence… that’s something every potential date wants to hear
