When To Ask Her Out To Avoid Rejection: 10 Ways to Do It Right

We've given you some tips on when to ask her out and feel better about it.

So you’ve been talking to a woman and you want to ask her out but you’re afraid of rejection. First things first — it’s completely normal so don’t beat yourself up about it. Knowing when to ask her out isn’t always intuitive. It probably doesn’t feel like it right now but that fear is entirely irrational. You’ll see for yourself soon enough.

Think about it objectively for a moment. What’s the absolute worst case scenario here if you get rejected? You may be playing out a horror scene in your head but in reality, the worst case is that she says no. If that does happen, at least then you know and you can focus your energy on other things, right?

Besides, that’s only one of the possible outcomes so let’s not focus on it. Confidence is attractive so let’s get you ready, huh?

How do you know when to ask her out?

Here are 10 simple things to think about the next time you’re looking to ask a woman out. Everyone has their own style. Don’t be afraid to experiment and leave a comment below with how you go.

1) Get your head in the right space

Before we even talk about when to ask her out, let’s make sure you’re in the right mindset. It’s no secret that confidence is attractive. If you aren’t feeling all that confident right now, you’re in luck. With a bit of practice, confidence is definitely something you can fake for now.

The best part is, if you fake it long enough you’ll actually start to notice the real thing coming through. If you need to, sit down a make a list of 10 things people like about you. Are you funny? Intelligent? Athletic? A great conversationalist? Whatever the case may be, figure out your own strong points and focus on those.

The thing is, confidence is a mental thing. If you spend your energy telling yourself you’re not good enough for her, you’ll be right. On the other hand, you are worth being around — so how about you demonstrate that instead?

One cautionary note I’ll add here is to work on this over time. See how people respond and adjust accordingly. Too much confidence is just arrogance and that’s not an attractive trait.

2) Dress to impress (yourself)

Continuing on from the previous point, make sure you’re dressed well. With that said, don’t fall into the common trap of just dressing for her.

Instead, dress however you feel most comfortable and confident. For me, that’s often a nice suit, my favorite pocket square and cuff-links. I know I look good in it and that confidence is something I can’t help but project.

What that looks like for you is entirely your call. Maybe you feel the most confident in well-fitting jeans and a T-shirt. If that’s the case, go for it and choose your date location accordingly.

Naturally, you should also be dressed appropriately for where you’re going. You won’t see me at the local dive bar in a suit, right?

3) When to ask her out? Gauge if she’s interested

If you know what signals to look for, this can be surprisingly easy. If you don’t, take a look at one of my earlier articles, “8 Different Tests To See If A Girl Likes You As More Than A Friend.” It will guide you through 8 of the easier signals to look for.

Paying attention to how her friends act around you can say so much. Likewise, what she’s willing to talk about and when. Sometimes these subtle things can give away so much information — it’s well worth reading.

4) Don’t wait for the perfect moment

The perfect moment for when to ask her out doesn’t exist. While Hollywood suggests otherwise, you can’t write a script for you both to follow. In the real world you just need to feel for a suitable time and go for it.

This is something I see from friends quite often, particularly on a night out. They sit there waiting for the right time and before it arrives, another guy starts talking to her. Make sure you make your move before she gets bored.

Whether the conversation is through Tinder or in person, keep it fun and exciting. If it starts to get dry or forced, it’s time to change the subject. If you’re getting signals to suggest she’s interested, it’s time to make your move. Now.

5) Isolate before you ask

This is something I find myself covering often. Asking her out in front of her friends is going to make her feel uncomfortable. Instead, find a reason to go somewhere alone together and do it then.

Ultimately you should be doing this quite a bit earlier. Preferably after you’ve established some rapport and comfort. It can be as simple as grabbing her hand and leading her to the bar for the next drink. Whatever reason you use, isolate and escalate quite quickly. Too long and she might get uneasy because she’s ditched her friends. Be sure of yourself and go for it.

6) Be assertive

This point seems a little less obvious than the others but it will make a difference for you. When you ask her out, make it as simple for her to accept as possible by being direct.

For example, which of these do you think sounds more confident and assertive?

“So uh, I was wondering if you’d like to have dinner with me some time?”

Or

“This is fun. Why don’t we go to [local venue] next Friday night? You have to try the cocktails there!”

Now don’t get me wrong, the first example is infinitely better than not asking her out at all. That said, if you’re going to do it, how much better does option 2 sound?

The confident approach means all she has to do is say ‘sure’ if she’s interested. You’re making life easy for both of you and leading the way.

This is positive feedback I receive so often on first dates.

“I loved that you were so decisive. I’m so tired of guys wanting me to decide everything we do.”

7) Assume attraction

No matter how attractive you may be, it’s easy to get caught up in your own head. It’s so easy to fall into the trap of thinking you aren’t good enough. If you immediately convince yourself that you’re beneath her, that’ll come across in your actions. Assume she’s interested in you until you’ve got a solid reason to believe otherwise.

Just last week I left a date thinking I’d been off my game a little. Halfway home I get a text from her with an implicit invite to a restaurant this week. Had I made the decision that I wasn’t right for her, I’d have never seen her again.

Instead, keep this point in your mind while you’re talking to her. This will see you acting differently (in a good way) and it won’t go unnoticed.

8) Make it easy to say no

I’ve covered making your invitation easy to accept but I wanted to mention the other side of it too.

Some pickup advice suggests that you should almost make it impossible for her to say no. Is that really what you want? Personally, my ideal situation is when she’s excited that I asked her out. Having to convince her to go out with me sounds horrible for both parties.

9) Asking her out is simple; don’t overthink it

You may be thinking to yourself “oh yeah, just like that huh?” but think about it this way. If she were to ask you out, what would you be focused on? The exact words she said or the fact that you were just invited on a date?

You will add some polish to this process over time but it honestly doesn’t make a huge difference. In pretty much any scenario, if she’s going to say yes then it’ll happen.

Rather than making a big thing of it, think of it like asking a friend to go do something. How would you do that? Just a simple “hey, let’s go do xyz next week”, right? Why should this be different?

As a matter of fact, that’s exactly how I got over this fear myself. I would think of somewhere laid back enough for a first date. When it came time, I’d pretend I was asking one of my (not single) female friends to go there. It made such a huge difference for me.

10) Know how to handle rejection, just in case

Remember how I said that you can’t possibly know what she’s thinking? That same thing applies here too.

If she does happen to say no, that doesn’t necessarily mean the end. Particularly if you already knew her, you may have just had bad timing. Handling rejection well gives you the potential for future opportunities. Besides, if you have mutual friends, blowing up at a polite rejection isn’t wise.

I tend to handle it one of three ways depending on her, the conversation and where we are:

  • A chuckle and a light joke; “ouch, my beautiful pride!” or “it’s the flawless hair tonight. It’s intimidating you isn’t it?”
  • A calm and collected “that’s ok” and move on with the conversation
  • A suggestion of a different day and/or location if she seemed unsure. This one is reserved for when she just seems uninterested in my chosen activity.

My sense of humour means the first one works nicely to defuse any tension. It could come off as extremely arrogant or cringe worthy though if not delivered right. However you choose to handle it though, keep it respectful and calm. I promise you’ll survive.

It should go without saying but the other reason to handle rejection well is basic human decency, right? Saying no doesn’t make her a bad person. Maybe you can even learn from it for future.


With these 10 tips, you don’t have any excuse not to go try it. For the most part, women are going to be very kind and caring toward you. Time to quit stressing about it on the couch and go put this info into action.

I guarantee you that when you do it for the first time after reading this, you’ll wish you’d done it sooner. It’s fun and exciting for both parties and you’ll feel so much better about yourself as a result.

Good luck!

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