Why “What Are You Doing Tonight?” is Not a Good Way to Ask Her Out

asking a woman out on a dateFor a while I couldn’t figure out why it bothered me so much hearing other guys ask women out by saying something like “What are you doing tonight?” until it dawned on me that it shows a serious lack of confidence with women. It goes without saying that confidence is one of the qualities that most, if not all, women are looking for in a guy. Being able to take initiative and take matters into your own hands, so to speak, is what turns women on emotionally, mentally and sexually. This doesn’t mean that you have to be controlling or overbearing, as that’s usually a major turn off, but taking a lead in subtle but important ways is important at all stages of dating, including the very early stages of asking a woman out and going out with her.

Many guys make the mistake of beating around the bush when asking a woman out for the first time or shortly after they started seeing each other. They would start “testing the waters” by asking her what she doing on that night, if she has any plans, how her week looks, etc… There is nothing per se wrong about asking these kinds of questions, but in the context if asking a woman out, it will hardly make you come across as the kind of confident man that every woman wants. There are only a few ways that kind of conversation go. The most likely one: ” – What are you doing tonight?  – I am busy doing (whatever). ” Is that conversation over? Probably. If she says that she is doing nothing, then it will look like you are trying to fit into her spare time like some kind of low priority person, and there is no reason in the world why you should be creating that kind of image for yourself.

Instead, you should invite her out. You should suggest a specific time and place to meet and go from there. Surprises are fun, and you don’t have to tell the girl you are going out your entire plan for the evening, but inviting her to meet and being specific about it, rather than wondering what her schedule looks like is a much better, and a far more attractive way of asking a woman out on a first date or any subsequent date.

If she is unavailable, you can always suggest a different time or a different place to meet. Being more direct about inviting a woman out doesn’t mean you can’t be flexible and considerate of her time and her circumstances. In fact, both qualities can compliment each other very well.

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09/03/2015 8:31 pm

Oh this is one of my pet peeves and I try to avoid doing this to people. It’s not a necessary question. Just ask me if I want to do ___. If I am truly busy but want to hang out with you, I’ll tell you and we can reschedule. Simple. This applies not only to dating but also to friends.

(But, for the record, it’s not that huge of a deal in the big picture. My boyfriend does this all the time, and well, he is still my boyfriend!)

09/04/2015 8:58 am
Reply to  Anne

Thanks for your input. Of course, once a relationship is established, this is an insignificant point and it’s not going to make or break a connection, but in the beginning, like you said, it’s not a necessary questions and it doesn’t add anything attractive about the person who says it.

Lila Marie
Lila Marie
08/01/2014 9:50 am

I get seriously annoyed when ANYONE texts me "what are you doing tonight?". If you want to hang out just say so. What's the worst that's going to happen? I say I have plans already.

08/01/2014 9:51 am
Reply to  Lila Marie

Good point. If a guy can't even take rejection by text, let alone on the phone or in person, what is he then made of?

12/09/2012 4:50 am

As someone who’s just experienced this, I couldn’t agree more. It’s really bad, guys. We like you to initiate and be specific, it shows that you care, that you have confidence and that you are not flakey in the way you show up in life (as the date is a sign of things to come in a shared life). More over, this type of question has the unfortunate effect of putting the onus on the receiver – so we have to share our plans when you’re exerting no effort to make any. Needless to say, I had to reply that I was busy, even though I wasn’t. It seems he’s learned, as he’s now come back asking me out to dinner. Result.

08/24/2012 9:01 am

women shouldn’t have to be so complicated to where u have to damn near go to school and get educated on how to talk to dem or what to say and how to say it… whateva happen to being you? cause i promise you most of them not online researching stuff to get a man cause no matter what they do…a man still gonna wanna holla if we think she worth it

Two of Us Dating
Two of Us Dating
07/18/2012 8:30 am

I could not agree more with your article! Asking that question definitely shows lack of confidence and that is the one thing that women are looking for. Not to mention it is way too much of an open ended question, you leave such a wide area for a response that anything could be said as an excuse just to get you off the phone. Personally, I love it when a man knows what he wants to do, I cannot stand indecisiveness. Decide what you want to do and where you want to do it and tell her what time your picking her up, how hard is that? Thank you for your insightful post.

05/29/2012 2:52 pm

I can't see how women like guys with confidence considering that they usually fall all over themselves precisely to undermine a guy's confidence.

Student And Teacher
Student And Teacher
05/27/2012 11:39 pm

J.N., I see where you are coming from. I think if a guy is overall confident and attractive (both physically and personality-wise), then something as little as this won't matter.

At the same time, I am siding with Arkady on this one. Not that "What are you doing tonight" is inherently and fundamentally harmful, but it is NOT NECESSARY and not your best option. It's beating around the bush.

I think the idea of putting her in a position to cancel with her friend to make her in some way beneath you, is redolent of PUA sophistry.

05/26/2012 5:25 pm

It’s very unlikely a woman will perceive a man as placing himself on the lower end of the priority totem pole with this line of questioning. She might even think he is being respectful of her time. One thing is for sure, asking her like this sounds run of the mill and boring. Ordinary questions like "What are you doing?" can place him in the wrong category as someone who is unmemorable. In order to standout from among the rest, don’t ask what she is doing on a certain night- Invite her.

Think of it this way: Have you ever received an invitation to a party that asked “What are you doing Friday night?” Nope, it simply reads “You’re Invited” followed by a list of event details. When you receive an invitation you know this person thought of you and wants you to come to spend time with them. You also know that you’re not obligated to go. If you want and are available to go you happily accept the offer. When you invite her out you are expressing this same sentiment. It is up to her to decide if she can or cannot make it. She may even change other plans in order to do so.

Besides, it is entirely possible that if you ask her “What are you doing Wednesday night?” and she answers, “I have plans to go out with my friend.” Maybe she really wants to go out with you and knows her plans with her friend are flexible. But she already answered "I have plans…" now she looks like a flake by saying “Oh, I can cancel that thing with my friend.” which now makes her feel like she’s being too available. Inviting her out gives her the option to make or change plans without the off chance you might be putting her in a rock and a hard place.