My best friend and I go to this fun Christian club every other weekend. There’s this guy who’s always there. He always hangs out with the same girl, but I’m not sure if they are dating since I’ve never see them hold hands or flirt. I always catch him staring at me.
I'm a pretty shy girl, so it’s hard for me to approach people, especially guys, but when they approach me I’m usually fine. I really want to get this guy to like me if he doesn’t already. Every time I like a guy he never likes me back and nothing ever happens, but I really don’t want the same thing to happen here. —Laurie
The first thing you need to do is find out whether the girl he’s with is his girlfriend or just a friend. I suggest that the next time you’re at the club, watch to see when she goes to the ladies room. Follow her and strike up a casual conversation – compliment something she’s wearing, her perfume, handbag, etc. Schmooze with her a bit, introduce yourselves and then say: So who are you here with? Most likely, she’ll either say a friend or her boyfriend.
If she says a friend, you’ll now be able to use her as your “wing woman,” since you’ve already made an initial contact. Either later that evening or the next time you go to the club, go up to her when she is with “him” and start talking. If she doesn’t introduce him, tell your friend beforehand that she needs to introduce herself to him first (since you’re shy) and eventually work you into the conversation.
Chat for about 10 minutes and then say you’re going to walk around. At that point, if he doesn’t ask for your number, at least you’ve had an initial conversation and will be able to easily talk again the next time you see him.
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