Dear J & J: O.K. , I've done everything you guys said about making eye contact, smiling, and creating conversation. (Actually it really works.) Now, how do I go about asking a woman I don’t really know for her number or seeing her again without sounding creepy, ‘cause after all, we just met.
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JACK: The best, though not always available, avenue is to steer conversation toward an activity or event that you will be involved in independently, but that you believe that she would also be interested in. For example, if she is or was an art history major, mention that you are planning to see the latest exhibit (or better yet, have tickets for the pre-opening gala). Then, having mentioned this, ask if she'd like to join you or find out more about it. Either she’ll say she’d like to join you (you have a date) or she wants more information about it (you have her number) — regardless, you've carried the ball further. And now, you can spend the rest of the week sweating over the Calendar section of the Times, trying to make good on your promise.
JILL: Jack’s right: the key is to connect something that she’d like to do with something that you’re already involved in or could be involved in. Not only does this create a built-in opportunity for you two to meet again, it signals to her that either (a) you share interests, (b) you have an "exciting" life that she wants to be a part of, or (c) neither (a) nor (b) are true, and she knows you just want her number, but she appreciates the effort enough to go out with you, anyway. For more information about making eye contact and meeting women you don’t know, see SharpMan Charm School: How to Be Charming.