A Step By Step Guide To Asking a Woman Out

By: Anna Wickham |

Man and woman shopping for vegetables

The process of going from complete stranger to having a time and place set for date number one is definitely a tricky one. It can be intimidating to approach a woman in person and get to know her. But this process doesn’t have to be so scary. All you need are these four techniques. Of course, I can’t guarantee she’ll say yes. But I can guarantee that if she turns you down, it won’t be because you did anything wrong asking her out.

Before we talk strategy, though, we need to address something.


How to Not Be a Creep


I’ve heard guys say many times that they’re afraid girls are going to think they are a creep when they try to talk to them. I can’t help but wonder if this fixation about not coming across as a creep is… well, making you come across as a creep.

Here’s why you feel like you’re a creep: because you want something from her. You want her attention, you want her number, you want to get with her. Anytime you are about to ask a complete stranger to give you something for no apparent reason, you’re going to feel uneasy.

To remedy this, you need to change your perspective. You are not talking to her to ask her for something. You’re talking to her because you have something to offer her. Don’t get me wrong, you aren’t thinking that you are the best thing since pumpkin spice lattes. But you need to have a giving mindset. How can you make her feel comfortable? How can this be mutually enjoyable, and not just enjoyable for you? These are things you can be thinking about when you approach her.

This is your responsibility not because you’re the guy and women should be catered to, but because you’re the one who is doing the approaching. If she were hitting on you, she should do the same thing. The sooner you make this mental shift, guys, the sooner you’ll be getting more dates.

Now, on to step one.


1. Ask questions that aren’t directly about her.


I know it sounds counterintuitive – aren’t you supposed to be asking about her? Yes, but hear me out.

Here’s what’s happening in your mind before you speak to this girl:

“I want to talk to the pretty girl. I can’t think about anything else because she is so pretty. I hope I don’t say something stupid. What can I say to her?”

A great way to come off as a creep is by being too fixated on her. She knows she’s a hot girl. She probably gets hit on all the time. That’s why you are going to be different from the rest.

You should care about what she is saying while at the same time not making her feel like the onus is on her. By making something else the focus of your conversation, you will make her feel like you are talking to her because of some event or situation rather than because she is a hot girl.

I know you think it’s impossible to strike up a conversation about common interests with someone that you don’t know. How can you make someone feel like you care about their opinion when they are a stranger? But the fact is that you already know at least one thing about her just based on where you both are. There’s bound to be something you can use to strike up a conversation.

Sound tricky? Don’t worry, it’s easy. Here’s what you do:

– Look around you. Shared experiences are everywhere. Maybe there’s a game on TV if you’re out. (“Are you a sports fan?”) Maybe you’re both waiting for the bus. (“Do you take this route often? I think I might have seen you before.”) Maybe you’re both waiting for rain to stop (“Last time it stopped raining after about 10 minutes, so I think we picked the right strategy.”). Maybe you’re both at a concert (“Have you seen them live before?”) Whatever you’re doing and wherever you are, look around to see what experience you are sharing that you can mention.

– Look at what she’s drinking. Is it beer? Wine? Whiskey? Whatever it is, ask her for her opinion on it in a way that shows that you are actually wondering: “Excuse me, I’ve been sitting here trying to figure out what you’re drinking. Is it _____?” Take a guess. Ask if she likes it. Is it on special? What the hell, order one for yourself in solidarity.

– What is she doing? Is she reading a book? Ask her if she prefers fiction or non-fiction. Is she trying to choose between two different brands of pasta at the grocery store? Give your opinion as to which is the best, or suggest a pasta sauce or recipe that goes with it. Be creative. You got this.


2. “I think you’d really like this.”


So you got a conversation started, and she already doesn’t think you’re a creep! Good job. Now it’s time to be bold. It’s time to ask her out.

“So… wanna hang out sometime?”


If at all possible, choose an activity related to the thing that you just talked about. It takes some practice to think of these things on your feet, but if you can manage it, it will increase your chances of getting a “yes.”

For example, if you’re at the grocery store talking about pasta, tell her you know a great Italian place that’s not too far from here. If you’re talking about the band you’re listening to, invite her to a concert of a similar artist next weekend. If you’re getting on the bus, tell her about a cool place that you’ve seen along the bus route that you’ve been wanting to check out.

Then, tell her that you “think she would really like” that thing. It takes the attention off of the fact that you want to spend time with her because she is a hottie, and it makes it appear as though what you really want to do is do this other thing, and you thought she might like it too.

Here’s how it sounds:

You: If you really like al dente style pasta, there’s this Italian restaurant not too far from here that I think you’d really like.


3. Make it as easy as possible for her to say yes.


She’s interested now. Don’t mess it up by asking her when she is free. Do not make her have to do any work.

Do this by pretending that you are headed there regardless of whether or not she is joining you. When you do this, your plans do not depend on her decision. That’s too much pressure on her! It’s enough pressure being responsible for her own time. She doesn’t want to be responsible for yours as well.

Instead, give her a solid date of when you are already planning on this activity, then invite her to join. All you need from her is a yes, and this date is on. There’s no pressure, because you’re headed there anyway, with or without her. This also eliminates the stressful and awkward task of comparing calendars and choosing a time.

Added bonus: it makes you seem more casual and less desperate because you’re not dropping everything to rearrange your schedule to hang out with her.

Now let’s add this to our previous strategy:

You: If you really like al dente style pasta, there’s this Italian restaurant not too far from here that I think you’d really like. I’m planning on going there Tuesday for dinner because they have happy hour all day. If you don’t have other plans, you should join me.


4. Don’t get her number – give her yours instead.


You don’t need to go through the painful process of trying to get her number. Just give her yours instead. Remember at the beginning when we talked about not asking for things from her? Here’s your chance. Give instead. When you ask her for her number, you’re intruding into her space. When you give her yours, you’re inviting her into your space.

It has another benefit, too: it comes across as cool and confident. You are so sure that she is going to contact you that you don’t need the security of that phone number in your hot little hand. You’re not even worried. You know she’ll get in touch. (I mean, you may actually be worried about it, but you’re not going to look like you are, and that’s what’s important.)

Let’s build upon our strategy one more time:

You: If you really like al dente style pasta, there’s this Italian restaurant not too far from here that I think you’d really like. I’m planning on going there Tuesday because they have happy hour all day. If you don’t have other plans, you should join me.

Her: Oh, ok… I’m not sure yet what my plans are, but I’ll see.

You: Cool, no worries either way. Here’s my number, just let me know if you’ll be able to come.

Her: Ok, thanks!

She’ll probably text you, if only because she really wants to try that pasta! (Kidding, it’s because she’s into you.) But if she doesn’t get back to you, don’t sweat it. It wasn’t in the stars. The important part is that you couldn’t have done any better.

– You were giving instead of focusing on what you could gain from the social transaction.

– You were observant enough to figure out something she might be into and took the time to pander to it.

– You made it as easy as possible to say yes.

– You didn’t intrude on her space, but you invited her into your space instead by giving her your number.

Practice makes perfect. Even if you strike out, you’re that much more prepared the next time you meet someone you’d like to get to know better.