How To Ask Women Out On First Dates (Without Being Creepy)

Men need to consider these essential expectations (and fears) before that first date.

How To Ask A Women Out On First Dates (Without Being Creepy) getty

By Kara Post-Kennedy

Look guys, we get it. We know you bear much of the burden of kicking off first dates.

We get how hard it must be to approach a woman cold to express an interest in dating her or ask her out. We understand that nerves may get the best of you and you may not know how to approach or start a conversation with a girl, let alone how to get her to be your girlfriend, causing you to end up over (or under) stating your case at the moment of truth.


Generally speaking, I do appreciate that there is an element of bravery involved. And yes, it can be flattering as well. That having been said, when you approach us cold we are keenly aware that your approach has to do with only one thing: how we look.

Spare me the comments about “energy” or “how she laughed” or “how she was with her kids.” I know that is what you might tell her, but she knows the truth…you like what she looks like.

So this sets you off at a disadvantage for sure.

Because all we are going to know about you is how you look (far less important to women than men) and therefore much more importantly how you choose to approach us. I thought that based on my own and other’s experiences, I could set up a kind of guide of “hits” and “misses” when it comes to the art of the cold approach before a first date.


RELATED: 5 Ways To Start A Conversation With Anyone. Literally Anyone.

Here are the most important tips you need to know about how to start dating the girl who catches your eye.

First the Don'ts:

1. Don’t give us your card on the pretense of wanting to help us with our taxes or paint our house or whatever-it-is-that-you-do.

I actually fell for this once and it was VERY awkward when I realized too late that the gentleman in question had no interest in “doing business” with me except euphemistically. I guess maybe you think you are “putting the ball in our court” but it essentially dishonest which is not a great start to anything.


2. Don’t go from zero to 60.

When you go from being the-guy-behind-me-in-the-checkout-line to the-guy-who-is-offering-to-cook-me-dinner-at-his-place in the span of 5 minutes, you are not likely to get anywhere (or if you do, I am desperate and will soon be watching your place through binoculars). It’s fine to chat someone up and gauge if there is any interest but tap on the brakes here.

3. Don’t stare.

This is a big one; I recently spent an entire meal out with friends with a guy at the bar staring at me so intently that instead of enjoying myself I was in panic mode trying to figure out if I knew him. He waited until we were on the way out to make his move, at which point I was so stressed out by his weird attention I’m sure I was rude. I’m not saying don’t try to make eye contact. I am saying DON’T STARE.

4. Don’t stalk us at work.

Yes, we see you. No, we can’t leave, we are working. This feels like a teenagers-at-the-mall move, btw, not a grown man behavior. I have heard a million variations on this theme but I’m just going to bottom line it as a no-no. If a woman is interested in you, she’ll let you know. You don’t increase your chances by making her feel trapped by your attention.

5. Don’t oversell.

Okay, you’ve approached, you are talking, it seems to be going okay. Do not tell us about your fancy car, your big bonus or your vacation plans. It’s tacky and insulting; it assumes we are shallow and attracted to shallowness. If you are going to go with that angle, you are 100% responsible for ending up with the kind of women who value that over your character, frankly.


6. Don’t open with sex talk!!!

Most of you know this (thankfully) but still almost every woman I know has a story. Here’s mine: his opening line was “I’d like to play connect-the-dots with the beauty marks on your body.” No, seriously. Another woman told me a guy approached her with “I don’t want to date you, but I’d sure like to have sex with you.” However harshly any woman responds to anything like this? You deserve it.

RELATED: 5 Tips For Talking To Her Like The Fun, Confident Guy You Really Are

Okay, those seem pretty easy to comply with, right? So how about some ideas for making the whole thing less awkward for everybody — what are the DO’S?

7. Do make conversation.

This is the lowest stakes way to see if she is interested. Is she making eye contact and answering in complete sentences? That is a good sign! Is she giving you “yes” and “no” answers and then looking away? That is a bad sign! Read the easy and obvious signs, please!


8. Do give her space.

Close talking and premature touching are going to send the wrong signal. Having a relaxed, open-body language that is respectful of her space will make her feel safer and more comfortable.

9. Do engage her companions!

If she is with people, don’t zero in on her and exclude these people from your attention. It makes everybody (especially her) more at ease if you acknowledge reality and gives you a much easier exit strategy if her response indicates one is needed. However, if she turns you down, don't then ask her friend out. “Sloppy seconds” is not exactly starting off on a good note.

10. Do pay her a compliment (if it is sincere)!

Hey, I am a fan of compliments in general, even when not attached to flirting. Complimenting others not only boosts their mood, it boosts yours as well. Even if she doesn’t want to go out with you, this will more than likely get you at least a smile, and that is always a step in the right direction, right?


Again, we are keenly aware that even if you are not “our type,” your (respectful) approach is a courageous act and should be responded to courteously. If you follow these guidelines and still get a rude response, then you just dodged a bullet.

Like the old fairy tale says, you need to kiss a few frogs in your search for true love—just keep the kiss metaphoric until you have actually gone on a successful date, okay?

RELATED: How To Approach Beautiful Women (Without Breaking Your Own Heart)

Kara Post-Kennedy is an editor and columnist at The Good Men Project; a blogger at Your New Best Friend and Huffington Post and former Editor in Chief at OTV Magazine and a Mom.