Q: Hi, Chris:
A shy girl in my work place is avoiding me. Whenever she sees me she gets nervous and confused. I want to ask her out, but I don’t know if she is interested or not ? THANK YOU.
-- Confused 30-year-old in Boston
A: Dear Bachelor:
Unless you're stalking the shy girl at work (which I presume you're not), then let's try an approach where perhaps she'll open up more easily.
You say she gets nervous and confused around you. That's a sure sign she may have a secret crush on you, too!
How about the next time you see her, find something to compliment her about and make sure it's genuine. For example, maybe she normally wears slacks or jeans to work, but one day she has on a cute, red dress. You can say, "Hey, Sally, great dress and color on you!" Then immediately start some idle chit chat. It can be anything appropriate like, "So what did you do last weekend?"
After she stumbles around and answers you, tell her something interesting YOU did. Then whether your conversation is awkward or not, go right into something like, "You know, I heard about a great art exhibit at the Museum of Fine Arts, and I'm wondering if you'd be interested in joining me next Saturday afternoon?"
If she's interested in you and available, she'll definitely say yes. When somebody likes you, they won't care so much what you do on a first date, as long as you ask them out.
Since you say she's the shy and nervous type, though, I recommend doing something where you don't have to spend the whole time talking. This means eliminate the traditional "first time" dinner date, until another time. Those can be nerve-wracking enough for non-shy types!
Beside the art exhibit idea mentioned earlier, you can take her to a ball game (find out if she's interested in the Red Sox!); or maybe grab an ice cream cone and take a walk in a public park; or go to a theme park if there's one near by (who doesn't love a roller coaster ride and a giant cotton candy?)
You sound like a nice young man yourself. Please go for it, and let me know what happens!