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Ask Him Out!


In honor of Sadie Hawkins Day, we show you how to extend that invitation, and share some true stories too!

by Margot Carmichael Lester

his coming weekend we celebrate Sadie Hawkins Day, so why not use that as an excuse to ask some lucky guy out? Wait a minute, you say: Who the heck is Sadie Hawkins? And how can I get confident enough to do the inviting? Let us help you with all of that.

You Told Us: “How I Asked Him Out”
Compiled by Sarah Nesmith

“I had a crush on a guy I saw at the gym. He was always wearing his iPod, so I never knew how to start a conversation with him. Finally, one day I summoned my courage, tapped him on the shoulder, and said, ‘Can you recommend any good new workout mixes?’ We’re having our third date this weekend!”
—Shauna P., Brooklyn, NY

“There was a coworker I was interested in but didn’t know how to ask him out. So one day after some big news at our office, I said, ‘I don’t believe in office gossip—on company property, that is. Want to have a cup of coffee after work and talk about what’s going on?’ It worked!”
—Karen A., Naperville, IL

“This may sound lame, but there was a cutie I always saw in my neighborhood and I didn’t know how to strike up a conversation, so I pretended I knew him from somewhere and said, ‘Hey, aren’t you India’s friend—from the brunch?’ I totally made it up, but it did get us talking. We've been dating for two months now.”
—DeNise, Oakland, CA
First, a little history lesson
Who is the namesake Sadie, and how’d she get so bold? A quick explanation: Cartoonist Al Capp created Sadie as part of his strip, Li’l Abner. Sadie was the “homeliest gal in the hills” whose prospects at love seemed slim. To help his character out, Capp scripted Sadie Hawkins Day as part of this cartoon in November, 1937. As part of the day’s festivities, the unmarried ladies of Dogpatch ran a foot race to chase down their favorite bachelor. Whoever got caught got married. The event was such a hit with L’il Abner fans that it became a real event.

Now, how to ask him
So, that’s the background on how Sadie Hawkins Day came to be. Since this is the one day a year when asking a guy out is totally encouraged, let’s look at how to do just that. Why not put some marketing wisdom to use for you? Jocelyn Fenyn, the former top sales executive for NBC Television and co-founder of Dinner Introductions, offers these smart tips:

  • Read him. “Assess your audience and quickly figure out the personality type so you know what you’re dealing with,” she counsels. “Are they all business and pressed for time? Or do they respond to humor and want to spend a little time schmoozing?” Approach the ones who have time to make eye contact and seem interested in being chatted up.


  • Create the connection. “Establish an environment of ‘let’s have fun’” she adds. ”You’ve got to find out their passion—their hot button—and then create the connection with the subject by asking about it and truly being interested.”


  • Remember to listen. “Contrary to popular belief, sales is not all talk,” she concludes. “Listen to what your subject has to say and don’t interrupt.”


  • Once you’ve completed these preliminary steps, it’s time to close the deal and “ask for the order,” in your case, a date. “If it’s been a good meeting and you’ve found out their hot-button interests, make the next move,” Fenyn says. “If he likes baseball, suggest going to the next Yankee game. If he’s knowledgeable about art, tell him you hear there’s a great exhibit at the local museum, and you’d love to go with him so you could learn from his expertise. Remember that when you close, it must have meaning and refer back to the connection you’ve already made.” That way, you’ve forged a bond, reminded him of why you connected—and you're ready to ask him out.


    Margot Carmichael Lester is a North Carolina-based writer and the author of The Real Life Guide to Life After College.
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