Centerstage - Chicago's Original City Guide

I'm single, cute, and in a severe dry spell. I'm tired of guys not asking me out even though they're clearly interested. What's the best way to go about asking out a guy?

It's great that you've decided to be more proactive. If you are in a situation where a guy is sending you the right signals, then chances are he would love it if you took the lead. At the very least he will feel extremely flattered.

When suggesting a date—no matter who is doing the asking—try the common ground approach and close with a specific plan. Find something that you have in common, and turn it into an opportunity for you to get together. For example, while talking about the fact that you both love baseball, you could mention that you have tickets to a game next week and ask him to go with you. If you don't feel comfortable with a straight-forward approach, invite the guy to a group activity. You could include him in happy hour or a brunch with friends; or get a ticket to a concert you know he'd like to go to and ask other friends to join you. This might ease some of your pressure, but still allow you some time to get to know each other. As he becomes more comfortable with you and catches on that you enjoy spending time with him, he might step up and do some of the asking.

While you want to approach these situations positively, try to prepare yourself just a little for the possibility that the guy might turn you down. It will not be the end of the world. Move on to the next cute guy who catches your eye!

Good luck,
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