Should I Ask Him Out Again?

Dear Brenda,

I have been hanging out with this group of guys for a couple months now and really enjoy going out clubbing with them.

Essentially, I had developed a crush on one of the guys before we started hanging out as a group. Before this crush and I had a chance to get to know each other, I propositioned him and he turned me down saying that he was flattered but didn't feel the same way about me as I did about him. However, he still wanted to hang out with me in the group.

Since then, we've really started to get to know each other and found out that we like the same music and other types of activities/interests. We have the same sense of humor and we both love to laugh. We're still hanging out in the group but I have started to get these mixed signals from him. I have to admit that I have been constantly "friendlier" to him than the rest of his group and have outwardly flirted with him even though my proposition was turned down.

In the beginning he was friendly but as we got to know each other more, I have noticed that he is outwardly flirting back...making eye contact, playing with my scarf while I'm still wearing it, picking up my necklace to get a better look at it, and lately, slipping his arm behind my waist as he is talking to me. Lately, when we say goodbye at the end of the night he will kiss me on the cheek (even in front of his friends). His friends seem to really like me to but definitely do not flirt with me like he does.

It's really driving me crazy! I had developed the crush when I hardly knew him but now I like him even more since I have found out that we have similar interests. I just don't know whether this is doing the "friendly male ego flirting thing" because he already knew I liked him and he loves the attention, or if he truly is interested in me now that he has gotten to know the real me. What do you think? If I were to proposition him again and he isn't sort of interested, am I going to lose out on that possible friendship?
- Iwannano

Dear Iwannano,

That's the pretty much the opposite of what you should do. So don't do it.

Here's my suggestion:

Stop flirting with him immediately. (you can do it). Be friendly with all the other guys, though. You have to be very subtle about this, but I swear, if you do this, he won't know what hit him. You could even act a bit bored when you deal with him directly. The minute you stop paying so much attention to him, it will peak his curiosity, and get him where it hurts, right in the ego. Chances are one or more of the other guys likes you, but didn't want to crash and burn because they can obviously tell who you're interested in. They wouldn't hang out with you if they didn't think you were some kind of babe.

I had a 50 year old friend (he's back on the dating scene) tell me the other night that he is more attracted to women who don't want him. That's actually very common. Men love a chase, so give him one. If you're too available, you aren't much of a challenge, especially when we're talking about the bar scene. Since he can't or won't ask you out, you have nothing to lose.

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