Wise Guys: Can't Women Ask Men Out?

photo by rick

Advice from three of our guy friends. This week a straight woman asks, “Why do some guys get freaked out if a woman asks them out, and act like she’s desperate? Is it because they feel like they have to say yes? Or does it actually make a woman seem less attractive to some guys, if she’s playing the opposite of hard-to-get? Do guys make assumptions about what a woman is like, based on the fact that she asks him out?

wiseguy_benStraight Married Guy (Ben): I would guess one of two things is happening here. Either you’re dealing with a really immature guy — a guy who doesn’t have a lot of experience with dating or who isn’t all that confident in himself — or you’re dealing with a guy who just doesn’t want to go out with you. Either way, there’s a strategy here for easily figuring out how a guy is going to react before you ask him out. It’s called “flirting.” Start slow, toss an innuendo here, a very casual touch there. If he returns the flirt then start ramping it up. Really, everyone – man or woman – should have a pretty clear idea what the answer is to “Will you go out with me?” before you even ask it. You’ve achieved “expert” flirting status when you can get your mark to ask you out first. Saves you money on the date while you decide whether he’s good enough for you.

Gay Commited Guy (Bradford Shellhammer): Yes, some men like women who are quiet, who play the part of the damsel in distress. They like the power struggle. For those guys I imagine it could be a turn-off. But for every one of those guys, the ones intimidated by strong and direct women, I bet there are even more who’d be welcome to women making the first move, being the pursuer. Yes, guys — hell, everyone — makes assumptions about people based on first impressions. Nothing new there. But women should be more aggressive with dating and asking guys out. I think it would, in the long run, save them a lot of headache.

anonymous_suitStraight Single Guy (Max): I like a girl who is hard to get. Us dudes like the thrill of the hunt and the time during which we don’t know if anything is going to happen. When a girl asks me out it is (most of the time) a thrill, but quite different from working hard for a lady, and eventually getting what you want. Suddenly, you realize that you are the hunted and this can
be either amusing and awesome, or a frightening realization that your game ain’t up to snuff. Personally, I’m quite intrigued by any girl who has the guts to ask me out. A girl who knows what she wants is a good thing. For all ladies considering such moves, however, I will point to this question as a good indication for the risks involved. We CAN get freaked out and you CAN look desperate if you do this in the wrong manner. If you ask a guy out, give him options. Let him feel a bit of power by picking the location, time or whatever. Just don’t walk up to him and tell him to take you out this Saturday and that you love sushi. Even if you’re a total babe, this is a strange move and will spook most men.

Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Straight Married Guy is Ben, a writer and artist living in Los Angeles who runs AdultParlorGames.com; our Gay Guy is fellow SUN blogger Bradford Shellhammer, the creative director of fabulis and a New York Times featured decorator; and our Single Straight Guy, Max, is a recent college grad in New England. To ask the guys your own question, click here.


  1. There is no reason why a woman can’t ask a man for a date.

    Women aren’t some prize, women are HUMAN not some wallflower!

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