Today I’m going to address a question that was asked by one of my phone-coaching clients. He recently met a girl online, exchanged a few messages with her, got her phone number, and spoke with her on the phone a few times. He swears this is the part that he always messes up and he’s very nervous about asking her out.

Simply put, you’re over-thinking it./span>

Yes, there are some specific ways that I think it’s better to ask a girl out depending on different circumstances. For example, I think as a general rule of thumb it’s better to have somewhere specific that you want to go with her. Rather than say, “Hey, do you want to hangout sometime?” it’s typically better to say, “Hey, I’m going to watch this local band play at XYZ on Thursday night. Let’s go have some fun! Are you free?”

There are some specific things that can be done to make the transition a little bit smoother, but in the big picture, they’re pretty insignificant.

Let me elaborate.

If you’ve done a good job of gaining the woman’s interest, she’s not going to be too concerned with how you ask her out unless you really say something off the wall.

If you’re speaking to a woman that you’re attracted to are you not going to want to hangout with her if she asks you to hangout the wrong way? Is it really going to matter if she says, “Hey, we should hangout sometime.” vs “Hey we should go to XYZ to listen to this band.”… ?

No, of course it’s not going to matter.

If she says something totally wacky, then maybe, but there’s a good chance you’re still going to want to get to know her if you’re really attracted to her.

I have had clients ask me if they should tell the woman that they hope she’s having a good day and then ask her out or if they should just ask her out… You’re really over-thinking things if it gets to that point.

If she’s interested in you and attracted to you, then just ask her out.

If she doesn’t want to see you, then you either asked her out too soon, she’s not that interested in you, or she’s the type of woman that expects her guy to be perfect. Let’s look at each one of these.

Asking her out too soon: Asking a girl out too soon can result in pushing her away. This is not a blanket rule. There are many times when things can happen very fast, but more times than not, guys pull the trigger too soon without getting to know the woman.

If you meet a girl online, message back and forth a bit, text a bit when you get her number, have a phone conversation or two, and demonstrate that you want to get to know her.

Same thing if you meet a girl at the grocery store, at a bar, or through friends. Build a little connection, and then ask her out.

She’s not that interested in you: If you’re pretty confident that you’ve spent enough time attracting the woman to you, you ask her out, and she doesn’t respond, she declines…

Then chances are that she wasn’t as into you as you thought she was.

She either sent you mixed signals or you misread her signals. There’s not much that can be done at this point except to take a big step back and try to build more of a connection before trying to ask her out again.

She’s looking for Mr. Perfect: If I ever find myself becoming hypercritical of how I’m texting a girl, talking to her, asking her out, there’s a good chance that I’m dealing with a woman that expects perfection. I don’t want to be with a woman like that and I don’t think you do either.

I can appreciate a woman that pushes me and challenges me in a positive way, but I won’t be with a woman that I have to walk on eggshells with.

There’s almost an intentional amount of imperfection that I will demonstrate to a woman when getting to know her to test and see if it rubs her the wrong way. Women appreciate men that put time and energy into small details, but don’t confuse that with women that are expecting perfection.

Asking a girl out should be fun, easy, and free flowing. Funny enough, when you relax a little bit and are a little less meticulous, your interactions will flow much smoother and you will attract women that are more easy-going, as well. So don’t over-think it, especially early on. You can perfect the way that you word things later down the road, but when you’re first starting out, just ask the girl out however feels natural in the moment.

As long as it’s somewhat “normal”, you should be fine.

If it doesn’t work out, there’s a good chance that one of the three things we’ve talked about is the reason. Get creative and push the boundaries after you’ve gained some more experience.

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