I am a pretty aggressive person, but I have only asked out 2 guys in my life. The first guy reacted the way my cat does when I turn on the vacuum cleaner, the second one acted the way you might if a dog walked into your office and asked you for help zipping up his pants. Suffice it to say, no dates resulted. Based on these experiences and similar collected data from friends, I eventually settled on a “I don’t ask, I answer” rule. It’s not that I can’t handle the rejection, it’s that dudes seem to freak out when put in that position.
I feel confident in saying that this is how a lot of other women think, too — we know that all that stuff in womens magazines about how guys would loooove to get asked out by a girl is crap. It’s bullshit, guys! When you are asked if you’d like to be asked out by a women, you are not thinking about your actual life. You are picturing the same imaginary women you think of when you say lesbians are hot. Instead, picture a dumpy woman installing a shelf in an apartment full of cats. Still into lesbians? Now picture your funny friend with the stringy hair and ill-fitting skirts who thinks you are hilarious. Still want to get asked out? Nope, and nope. We know that.
Which is why so often it’s left up to you, fellas. If you are interested in a girl, just ask her out. What’s the worst that can happen? She gets offended that you implied that you are in the same league and makes fun of you in her blog? Uh, I mean — no — no one would do that. Haha, no. Ha. Hm. No the worst that could happen is she says no and you all get on with your lives. I have been asked out by guys I have said no to, and you know what I think of them? I think they are pretty fucking cool dudes. Seriously. Why would I not? CLEARLY they have great taste. I have even forgotten that some of them ever asked me out, and just ended up friends with them.
And what’s the best that could happen? Boning. Love.
But here’s the thing — when you ask, do it right.
- Have a plan. — if you say “Would you like to go out to dinner at Awesome Restaurant?” her answer is much more likely to be yes than if you say “want to do something some time?” Because, let’s face it, she probably isn’t sure that she DOES want to do something with you, but who doesn’t want to go to Awesome Restaurant? A good plan has tipped the scales more than once.
- Enjoy asking. — if you look or sound like someone is snatching at your balls while you pop your question, she’ll say no. She just will. It gives off the air of “there is a man with a gun watching us and he will shoot me if you agreed to this.” Relax, plant your feet, smile casually, and ask her out. Email is ok, also. NO EMOTICONS.
- No “negging”. That shit about being mean to girls when you hit on them? That is a trick to make you act confident, but it makes you a confident douchebag. Skip it and act like a confident good guy.
- No matter what she says, smile and thank her. — you never know who’s going to be hotter or more single next year. Stay in the game. This isn’t over until someone is married.

I’d argue your point about the worst that can happen is “she says no and you all get on with your lives” is exactly the same if a woman asks a man out. You got turned down twice? Oh, Eliza. Men get turned down a dozen times until they get a yes (unless you are R.D.jr. of course).
Otherwise, good advice. I would also add “Make your intentions clear.” Saying, “Hey, let’ go see Pineapple Express” can easily be accepted when they don’t realize it’s a “date.” Nothing is as fun as thinking you’re on a date only to spend three hours hearing about the boy they think is adorable. (Oh man. I’ve been on so many of those.)
I, um, asked out my husband (before he was my husband, obviously.) He hesitated. The hesitation in which I died a thousand deaths. But then he said yes and then later I moved in and then later we got married. It was not the first time I’d asked a guy out, but it was the first time a guy said (long pause) yes. Sometimes it’s worth the humiliation, is all I’m saying.
My wife proposed to me. I’d been married and damaged before so she knew the chances of putting myself out there were pretty slim. We’d been living together awhile and exciting as it was, the only response I could immediately come out with was “Why do you want to have less sex?“
It worked out, but I gotta side with Eliza on this. Instinct A was to retreat when asked, fortunately my wife knows my sense of humor, and I would have eventually asked her. She just got the cojones first.
I’m in a position to ask women out for the first time in 12 years, and this is a really nice refredher. Thanks, Eliza.
Why expect a guy to be braver than you? Double standard here.
C. Scott is right except for the “Pineapple Express” suggestion. If it’s gotta be a frat-boy-humor kind of film, pick something smarter like “Tropic Thunder” unless you’re under 21.
All the other points are golden. So glad you asked…
Here’s where I need an emoticon at my fingertips.)
I am not expecting a guy to be braver than me, MOTHER. I am just admitting that we are part of a culture in which most — not all — guys freak out when asked out by a woman, whereas most women know how to take it. Everyone should be ready to break the rules (and The Rules) for people and situations that are worth it, but in most cases, these are standard operation procedures as I see them.
By the way, this comment is from the woman who always told me “if they want to date you, they’ll ask” and was horrified that I ever called boys. Ah how the long wait for grandchidren changes things.…
Way too much thinking here. (both genders) Just do it.
Women have a way of asking men out. It’s called flirting. Make him confident enough to want to ask you out. The direct approach is a little emasculating. Flirting may not work, but the direct approach is even riskier. Be nice if it weren’t so, but that seems to be the world we live in.
I may be unique, but I’m also really thick. I never know when a woman is flirting with me or just talking or whatever. Unless she’s forward and asks me out I don’t think I would notice that there was anything going on besides being friendly.
So I would be honored if a woman asked me out on a date.
My wife wouldn’t care for it too much, but I’d be flattered.
Aren’t you afraid this is going to give a green light to open the floodgates (and any other permission giving euphimisms) for all the guys who were secretly considering asking you out to do so?
Nah, the fallout hasn’t been too bad. I think people get that it isn’t secret messages about me. Anyway the it’s better to ask than bore holes into the back of my head. That’s the other point I didn’t mention: we can tell when someone is interested in SOMETHING, but it’s sometimes hard to tell if they are interested in dating you or in peeling off your skin and wearing it like a coat. May as well ask and at least make it clear that you are not a murderer.