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How to ask out a guy on the sly

How can I go about asking a guy out? I’ve liked this guy forever, but I’m scared to say, “Ya free Saturday night?”

Dear Ready,

Sometimes, fear is your friend. Unless you and this dude are doing some serious flirting and he’s giving you a bright green light, it could be risky to ask him out. You don’t want to put him on the spot, and he might need time to evaluate his feelings—and whether or not he’s willing to make them public. A safe way to ask a guy out is something like, “Will you be at Stephanie’s party this weekend?” This shows him you’re into him, but in a discreet way.
You could also say, “Some of us are going bowling tomorrow. Wanna go?” Of course, if you want to go for broke, you can ask, “Wanna take in a movie Friday night?” He might say, “Sure.” Or he might say, “Sorry.” If he declines, do not—I repeat, do not—say, “Then how about Saturday or Sunday or next weekend or the weekend after that?” You want to seem interested, not desperate. Oh, and make sure you’ve talked to your parents about going out. It would be pretty embarrassing if your crush said, “Sure,” but your parents say, “No way!” One other thing: You ask, you should offer to pick up the tab.
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BY CAROL WESTON ON 4/16/2014 12:00:00 AM

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