We're both shy - How do we get together?

Dear Brenda,

I'm not sure if this guy at work likes me so any input would be greatly appreciated. I worked with him once and since he seemed decent i.e. nice to me, I tried to go talk to him afterwards, but he wasn't that talkative e.g. wouldn't really look at me, didn't say much. I also asked for his contact information but he acted all flustered, blushed, looked down and wouldn't say anything. I sort of interpreted this lack of an answer as his being already spoken for (has a girlfriend, or is married) and since I am a shy and sensitive person, I haven't talked to him since which was 10 months ago. The weird thing though is that I have seen him staring/watching me out of the corner of my eye at times. And he has also held the door open for me when I didn't know he was behind me (not a significant action, of course, but just my observation). I don't talk to him anymore but I'm just wondering what his behavior could mean. Thanks in advance!
- dnlk2

Dear dnlk2,

It's really difficult to get together when both parties are so interminably shy. It sounds like he's interested, but not getting clear enough signals from you. Typically, men look for clear signs of interest from a woman before they pursue. The clearer the signs, the easier it is for all involved. If you're shy, it makes it that much harder. If you're both shy, then one of you will have to shake things up.

So... you have nothing to lose by sucking it up and making the first move. Throw on something clothing-wise that makes you feel great, hold your head up, walk over to him, smile, and start a conversation about current movies, a topic that almost everyone can easily participate in. Hopefully, if he doesn't pass out, he'll be able to handle his half of the conversation. When he mentions a movie that he'd like to see, ask him if he'd like to see it with you. If you don't feel comfortable asking him out, then drop the big hints - tell him how much you'd like to see a certain film, or a gigantic hint - the film he mentioned. That's pretty clear. If he says yes to your invite, then you've just made it easy for him, and you get your date. If he says no, then I doubt there's much hope for the guy, or he has a policy against workplace dating, or he'll probably tell you that he's seeing someone. But dnlk2, do you really want to wait ten more months to find out?

If anything, you'll feel much better about yourself after having given it a shot. Sometimes that's all you need to do to start something great. Speaking as the former winner of the "shyest person in my senior class," I've realized that we tend to make it a bigger deal in our heads than it really is, and the braver we try to be (even with baby steps), the quicker we shake the shyness.

Also keep in mind that plenty of women who aren't shy at all have had to set the gears in motion to get the men they want.

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