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Dear Miss SmartyPants,

So this is an interesting one ... This girl at work and I take lunch at the same time, a little earlier than most people, so it's usually just the two of us. This has been going on for about three or four months now. She's very attractive, we have quite a lot in common, and we manage to have interesting conversations five days a week. I should ask this girl out, right?

So I was doing a little homework, asking our mutual friend about her, when the friend tells me she has a boyfriend. I'm a little confused by this, because in the entire time we've been talking, she hasn't mentioned a boyfriend once. Don't you think that detail would have come up by now?

Now obviously, she has every right not to tell me this, but everyone but me, including my boss's wife, just knows this as a matter of fact. I'll admit I haven't explicitly asked her "do you have a boyfriend," mostly because I don't want to intimate my attraction and make things weird, but I'm just trying to figure out why someone would actively avoid mentioning a boyfriend: in fact last month she didn't mention him when answering the question "So what are your plans for Valentines Day?" (I had asked specifically to find out if there was a guy in her life, but she kind of talked around it and never really answered.)

OK. Truth is, I just want you to tell me she's totally into me and I should go for it.


Dear Perplexed,

She's totally into you. Go for it.

Or, what I was thinking before you handed me my line: She hasn't mentioned a boyfriend, so ask her out. She knows what her relationship is better than your mutual friend or boss's wife does.

But, in the spirit of exploration, let's try to figure out what may be going on. I'm just speculating here, but my guess is that she enjoys your company and thinks that if she mentions her boyfriend, you may lose interest in conversing with her every day, and you might even change your lunchtime in order to avoid the frustration of being around someone who is desirable but unavailable. She probably suspects you are interested in her, and she's enjoying the flattering attention. She no doubt thinks this is harmless, and it is, but it is also just a little duplicitous. Following this line of thinking, she may be, in a way, stringing you along for her own ego satisfaction.

Now that I've painted a picture of a conniving, self-centered little twit, let me back-pedal. After all, my guesses are just that ... guesses. We have no idea what's going on in her mind. Maybe she has a boyfriend that she is getting tired of and she is attracted to you and has been "trying you out" as a more desirable possibility for a boyfriend - or at least, someone to go out with if she breaks up with the current boyfriend and wants to re-enter the dating market. If that is true, she's no doubt been waiting for you to ask her out.

Third possibility: We're over-thinking things. We'll never know what's in her mind until you ask her out. Well, we still may not know what's in her mind, but at least we'll know whether or not she is interested in you, and if she is interested but has a boyfriend, what she intends to do about that. Remember, faint heart never won fair lady!

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