[awkwardsaurus]

I am a twenty-something interested in a twenty-something, but I don’t know how to proceed from there. We knew each other in college, and we recently got re-acquainted over the past summer. She met my friends, we roamed around DC a bit, and so on. Now I’m wondering if we can be more than friends. I’m not even asking for an instant relationship, I’m just hoping for a mutual understanding that we’ll see how things go (fingers crossed for hand-holding privileges). The thing is, though, I can’t tell how interested in me she is. She’s often quiet, a lot like me, and it can be really hard to tell if she’s enjoying herself. On the other hand, she trusted me enough to call me about picking her up from the metro after missing her bus at night, and we may be planning to see old friends at college together (well, maybe not together, since they’re her friends, but she trusts me to drive). I guess I’m wondering is 1) Is what I’m looking to ask her a good idea and 2) What is the best way to go about it?

[April Masini, your AskApril]

[quote]I guess I’m wondering is 1) Is what I’m looking to ask her a good idea and 2) What is the best way to go about it?[/quote]

If you’re looking for “a mutual understanding that we’ll see how things go….” the answer is no. It’s not a good idea to pursue that goal. Dating isn’t about mutual understandings — that’s the stuff of legal contracts! 😆 Instead, consider the dynamic where men chase women and win them over. 😉 That would require you to pursue her by making her feel good about herself when she’s with you, going out on a limb and flirting with her, and then, simply taking the next step to ask her out on a date! The best way to go about it is to call her up on the phone (women love to hear your voice), or else ask her in person. Figure out something in advance, like going to the zoo and lunch, or a dinner date, or a movie, or some great outdoor concert or a museum date — and tell her you’d like to take her out. Would she like to go to dinner (or whatever it is) on Saturday? If she says yes, you tell her that you’ll pick her up at 7, or whatever time works.

Hope that helps!!

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