This topic came up recently on Twitter: Should a girl ask a guy out?

specifically, @Cryptic Fragment posted: “hey GUYS…r you ok w/a woman asking you out? if you were interested wouldn’t you ask HER out? and how would you like to be asked?”

I replied (in far more than 140 characters, the elipses designate the separate twitter posts:)

@CrypticFragment I think it would depend on the situation. There was a song, “He’s so shy” about a guy who couldn’t get up his nerve … on the other hand, some guys, asked out on a date, would be prone to take advantage of the situation …. negotiating with them is going to be problematic under any circumstances …

Right away I knew I had simultaneously said too much and too little. This was a blog-sized, not a twitter sized, problem.  I also asked Bill Cammack about it and he did a man-on-the-street interview about whether a girl should ask a guy out which, since he is in New York, focused on how he and friends from the bar scene might like a girl who shows some interest … how long the relationship will last, or what is its purpose, is undisclosed.

So, should you ask a guy out? Well, it depends. I’m going to write a quiz and using the answers you will be able to decide. But first, determine what the situation is with his not asking. There’s two basic potentials: First, that he’s so shy you haven’t really established a repoir with him, or second, you have a good repoir and you think he likes you, but he’s not asking you out.

If he’s a quiet type, and you think his social life is constrained by his shyness, before asking him out you might consider:

1. Does he look at you … across the room especially?

2. Do you feel in your heart that he really likes you, he just needs a little encouragement?

3. If it’s his personality that causes him to hesitate, are you into a guy who’s shy and hesitant? They don’t change, you know, just because you’re in a relationship … it he’s shy, he’s going to be shy.

4. If it turns out that for whatever reason he doesn’t accept your invitation, can you take the disappointment? Do you think he’s “worth” the risk?

On the other hand, perhaps he’s acting like he’s interested, but just not asking you out. This is pretty frustrating. In this case, it’s likely you can get him to go out with you if you ask, but have you considered:

1. Maybe he’s ‘s in another relationship — or sort-of-relationship — that he might not be talking about? Perhaps he’s waiting to see what’s happening with his current situation and considering asking you out later? Do you want to go kicking the door in now if that’s the case?

2. He might have personal plans or issues that make him not want to enter into a relationship, and since he does like you, he feels you’d be hard to escape once you’ve gone out a few times …so he doesn’t want to get started.

3. You might be sending him negative messages without realizing it. He’s so dynamic that you’re making fun of him to get attention, and he actually thinks you don’t like him.

4. Maybe he’s like that with everybody. It hurts to say it, but there you are.

We hear a lot in business about being pro-active. I think, in sum, there are situations where you may lose the possibility of learning more about someone if you don’t, as a girl, ask him out. Whether you think the proactive approach, which is asking, is going to work for you really depends on how highly you rate this guy and how many other opportunities you’re getting.

In the end, you really have to live this problem yourself. I would only encourage those who face it and can’t stop thinking about it — to ask him out, to try to get attention, or whatever. If you don’t take some action, you’re in danger of feeling later like “I should have asked.” And to me that seems worse than if you ask and it doesn’t go as you hoped.

@CrypticFragment let me know if you get anywhere with this.