Intimacy Loneliness Miscellaneous relationships

Guys: How to Date a Woman

Whether you have six-pack abs or a beer gut, you can do these things...


I have been on a fair amount of dates in my lifetime.

I’m not perfect, but there are a lot of things I hear from both female friends and the women I date on which we could improve. This post is not to say ‘all women are perfect and men need to step it up,’ because that’s certainly not the case. But this post is directed toward men in the hopes of encouraging them to become the man that their girl will want to date.

You don’t need a six-figure income or bulging biceps to woo a girl and show her you mean business. So here are some simple observations that all of us can employ to become better daters. If that’s a word.

Be Confident

Easier said than done, right? Easy to say for millionaires, models and ivy league grads, right?


I cannot tell you how many girls have complained that the guy they like simply won’t ask them out or respond to their hints. Many women don’t want to don the proverbial pants and ask the guy out, but there are plenty of hints they may drop, such as texting, calling, being physically close to you, touching your arm, etc.

To this, the guy will respond, ‘but how do I knowwwwwww that that’s what she means?’

There is literally one way to find out. Ask her out! If you like her, take the risk! Many guys I have talked to have the same response: But I’m not sure if she’ll say yes…

Well, that’s exactly the risk you take. And in this case, you have so little to lose. Worst—and I mean the worst—case scenario is that she says no, she would just rather be friends. And if she is mean about it, then you probably didn’t want to pursue anything in the first place.

We have come to fear rejection so much it’s a little absurd. Girls are scary but not that scary.

Don’t be timid.

Granted, there are times where you may not be attracted to a certain girl for one reason or another and don’t want to ask her out. In this case, assuming you see each other a fair amount, communicate that to her, so she’s not left wondering when you’ll ask her out. Yes, it will be awkward but just do it.


Recently I have been seeing a ravishing woman who has recounted her own tales of past dates (or were they dates…?). And she is not alone.

It has become common for guys to ask women to

hang out,


get some dinner,


go to this event or that,

do some homework at a coffee shop,

et cetera.

And all of these leave the woman wondering: Did I just go on a date, or does he just want to be friends?

If you like a girl, let her know by using the simple 4-letter term when you request her company. If not, try to make that clear as well (Though whoever asked my current crush to go stargazing wore a pretty thin veil).

I think the struggle I’ve had in the past, being a guy in this situation, is not yet knowing whether I actually do want to pursue this girl, so I’m dipping my toe in the colloquial waters. And that’s a valid place to be. There is no easy answer, as every individual situation is unique. There is quite a bit of gray area here. Just try to be as clear as possible with what it is the two of you are doing.

Tips for a good date

Ok, so you’ve asked her on a date, she said yes, and now you have to figure out what to do. So here are a few simple do’s and don’ts to keep in mind on the big night:

Do: Go into the night with an open mind. You’re getting to know her, so do just that.
Don’t: Have wild expectations that you’ll get married next week, that you’ll fall in love, that she’ll sleep with you because you paid (That’s another whole article), or that you’ll know everything about each other by the end of the night.

Do: Have a plan. Make reservations. Call ahead. Set a time. Know where you’re going.
Don’t: Go in blind. It’s not caring or thoughtful to just ask her where she wants to go, or what she wants to do. You’re the one who asked her out, so you should be the one with the plan! Women like a man with a plan.

Do: Pick her up at her house.
Don’t: Tell her where to meet you.

Do: Open the door for her (restaurant and car).
Don’t: Be weird about it.

Do: Listen and ask questions. And listen more.
Don’t: Talk about yourself the whole time or try to impress her. Just be real. Confidence comes in being who you really are and owning it, not inflating yourself to someone you think she’ll like.

Do: Pay.

Do: Breathe.


I know this post seems very black and white. I can already hear the resounding chorus of AMENs from all the single female readers (Don’t get too excited, you’re next…..maybe. If I find the courage). But I know that there are a million different situations and these things are constantly in flux.

But there are a lot of things I see as patterns happening in our culture, and not all of them are healthy. Centrally, I hate to see men miss out on great women because no one has ever encouraged them, taught them the right way to do things, or told them to be bold and courageous. I was fortunate enough to be raised by a father who loves my mother well, and taught me to do the same, but I realize that’s not everyone’s story.

I guess the overarching themes boil down to these:

Communicate your intentions well.

Be thoughtful and considerate in all of your actions. Your job is not to impress her, but to care for her and get to know each other authentically. Good men don’t lead by overpowering or impressing, but by serving.

Plan, make decisions, and be confident. You can do it.

Let’s be men who treat the women in our lives gently and courteously. May we be courageous and tender at the appropriate times. And may we give the women we date a story they can’t wait to tell their friends about (or at least, may they respect us despite the outcome).


14 comments on “Guys: How to Date a Woman

  1. Pingback: Dating Tips – Beautifully Broken

  2. I have had a very similar post bouncing around in my head for a few months now! It will soon come out, but right now it is still in my head…but you touched on many things I was thinking!

  3. I for one enjoyed reading this, and I’d like to read your thoughts for the girls! 🙂

    I really enjoy your blog Ethan, thanks for keeping it going and being so open. 🙂

  4. I’m one of the women who said, ‘Amen’. Whooo!

    Thank you for having a heart for men to man up 😀

  5. Hi Ethan, I thought your article was great with one exception. Unless I know my date well and trust him, I will meet him at the restaurant or wherever. Because, safety first. I’m not riding in a car with a guy I don’t trust.

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