Common Mistakes I Think Men Make When Asking Out/Dating Women

Listen, I’m not a dating expert, I’m not a guru or a love scientist but I can tell you one thing: I am in fact a girl. Being a girl who is moderately attractive means that I have been asked out multiple times by multiple men and have been on many dates, which gives me enough experience to say there are definitely some guys out there who make some clueless mistakes. After a long discussion with a group of my lady friends, I compiled a list that contains things to avoid doing when asking out a woman/when you’re on a date.

Common Mistakes I Think Men Make When Asking Out/Dating Women
DISCLAIMER: Try not to take this so personally, because I know there’s going to be sour haters who complain that I’m just an ungrateful woman, that I don’t know anything, etc, etc. This is all in good fun and they are just suggestions, you absolutely don’t have to take my unlicensed advice (obviously) and can do things however you want. But, if you want some things to consider for your future dating endeavors, please continue on and enjoy the take.

Asking to “hang out” instead of go on a date

I’m sure many people are wise to this by now, but if you ask someone to hang out, that’s not quite the same as asking them on a date, especially if you have been friends with this person prior to making any romantic interest known. By asking someone to hang out, you might think you’re being smart by making the encounter casual and easy to retract if things go wrong, but you also put yourself in a position where you might not be seen as anything more than a buddy. I mean, you hang out with your friends; you go on dates with people you’re interested in.

So instead of worrying if she’ll find it weird or if it ruin your friendship, gut up and ask the girl out on a DATE. If you’re worried about losing her as a friend, be really cool about it and assure her that you have no expectations and won’t blame her if she decides she isn’t okay with it. I’ve had to do this with guys before and you know what? We stayed friends. It is possible to be friends with someone you had romantic feelings for, if you choose to. I don’t blame anybody who chooses not to, though. It isn’t the same for everyone.

Saying “I’d like to take you to/buy you dinner” when you really want to go Dutch

Wanting to go Dutch on a date is totally reasonable. Sure there may be some women who have an issue with that and you can foot the whole bill if you really want to, but if you’re a more modern guy then you need to make sure that this information is clear to the woman you’re going out with.

Not all women expect you to pay for a date, but a lot are under the impression that if you invite them that you’re offering to pay for everything. A good way to avoid any confusion is to avoid saying this like: “I want to take you to dinner” or “I want to buy you dinner.” When you say things like that, you put the woman in an awkward position of expecting to be paid for when really that wasn’t your intention; you can’t just assume she’s all evil and like she expects to be paid for unrightfully if you word it like that was your intention to begin with.

I always offer to go Dutch, but not all women are the same and may misconstrue you offering to specifically buy them dinner or take them out to dinner as you offering to take them out for a free meal. If you don’t have any intention of doing that, ask if she’d like to go to dinner, or if she’d like to split on dinner. At least then she will either be unsure enough to bring her wallet or she’ll know what to expect. If you have even more guts, just flat out ask her if she doesn’t mind going Dutch. Most women won’t mind.

Bringing sex up TOO EARLY

You being sexually attracted to a woman is normal. No woman out there will deny that, and if she does, well, she clearly lives under a rock so forget her. But having said that, a lot of things are normal: farting, clipping your toenails, hocking up a dirty loogie that has been caught in the back of your throat all day – you get my point. Those things are natural, normal things, but in the wrong place and time, they can be repulsive. The same goes for getting sexual with a woman.

First dates and during the “getting to know each other” period is typically not a good place to bring that stuff up. Sure, she may have amazing tits and you may wonder what colour her butthole is, or maybe you want to know if she’d be into foot stuff or if she’d be willing to dress up as that nanny you had when you were 13, but that doesn’t mean it’s appropriate to ask her yet. If you barely know the girl, those kinds of questions are off limits. The only time they aren’t is in a hookup situation with a girl who you are pretty sure is looking for the exact same thing you are or if she initiates the sex talk first.

Acting like she’s doing you a favor

Being happy and grateful that a girl agreed to go out with you is great, but like I have said in the past: quit acting like this girl is saving you from eternal loneliness by agreeing to go on ONE DATE WITH YOU. That screams desperation and a lack of self worth. She agreed to go out with you clearly because she saw potential in the idea that you two could be compatible, or at the very least she is open minded and willing to see where things go. That means that you were too weird or repulsive enough for her to instantly reject you, which is a victory, stop acting like she is a total saint and like she’s doing you the biggest favor. You are valuable, you could be a great boyfriend, you’re cool as fudge, get rid of this mentality that women live on a pedestal far above you.

So none of this:

“Thank you so much! I’m so happy you said yes! I was worried you’d say no!”

“Thanks again for coming out with me, it means so, so much to me!”

“I can’t believe you said yes, I’m so happy you gave me a chance!”

Sure, thanking someone for coming out and having a good time at the end of the night is totally normal, but you don’t need to thank her over and over again from start to finish. If she accepts your proposal, you can answer with a simple: “Alright, that’s awesome. I’m looking forward to it.” You don’t have to answer with: “Thank you, thank you, THANK YOU!

Come on man, stop that. You're worth going out with, just believe in yourself. Damn.

Making the entire date about her

There’s definitely some women out there who will hate me for this but the date isn’t just about making sure the girl is happy. You matter too, and therefore the date should be equally about her getting to know who you are as it is about you getting to know her. While it is expected that you court her – especially if you asked her out – that doesn’t mean she is the only thing that matters. The conversation shouldn’t be all about “20 Questions w/ Stacy” or “An in depth interview w/ Jennifer.” Don’t be afraid to direct the topic back to you and your interests every once in a while; I mean, if the focus of the date is on nothing but her, how is she going to know whether or not you’re even a suitable companion to begin with? All you did was talk about her.

By all means, show some romantic gestures, be genuinely interested in her and what she has to say, but don’t be afraid to bring the conversation to your side as well. You’re just as interesting and as important as she is.

Honestly, no fancy way to end this one, just thank you as always for reading and I hope you got something out of this take. You guys enjoy the rest of your week and I look forward to your comments.

RJGraveyTrain is a GirlsAskGuys Influencer
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Most Helpful Guy

  • I think the first one is very important for a lot of guys who mean well. Definitely make sure there's no mistake what you're asking a girl to do with you. I've seen this happen several times where the girl thought (or at least told the guy she thought) that he was just wanting to hang out as friends. But all of them are good. Solid take :)


Most Helpful Girl

  • about #1 and #2 YES I agree

    sometimes, it's so frustrated that you're happy your crush is finally asked you out, just two of us, but there... it's so confusing either it is a date or just two friend hanging out... so we'll assume he's not interested and move on... and finally we met another guy... THEN someone will tell you that "uh, the guy is actually really like you, but he's afraid to confess or do anything that lose you as a friend if it's not work out.."

    I really think we should have men's dictionary too, to allow us read their mind too.. LOLZ


Join the discussion

What Guys Said 45

  • "I am in fact a girl. Being a girl who is moderately attractive means that I have been asked out multiple times by multiple men and have been on many dates, which gives me enough experience to say there are definitely some guys out there who make some clueless mistakes. After a long discussion with a group of my lady friends, I compiled a list that contains things to avoid doing when asking out a woman/when you’re on a date." - Well, you're bragging a great deal for one, and only talking with your lady friends isn't enough of a survey. Your points are really nothing that hasn't already been heard of. And I'm sorry, but it does get tiresome to keep hearing about all the "mistakes" and wrong things guys are doing in dating. For once is there anything GOOD females can have to say about males and dating? And is it also possible that females AREN'T doing all the right things like they think they are?

    • I don't consider that bragging, if I was bragging, I'd be more of the tune of: I'm God's gift to men. I don't see how stating that I'm female and that I've been on a lot of dates would be considered bragging, especially considering that I'm still single so that suggests that many of them didn't pan out. I'm not at all, but if you found the points so tiresome then perhaps you shouldn't have read it. Like I said in the disclaimer, it's all completely up to people who have the desire to consider it to take the points if they want, if you don't agree or don't like it you are at your own discretion to completely pass it up. I will however take your end comment into consideration and make a female version of the same take to even the playing field. Because women definitely aren't innocent.

    • Good grief you women made dating so f*** difficult. When I was dating it wasn't that hard. Women wanted to date and impress me.

    • @burpzzzzz Dude I posted this a long ass time ago and am literally in a relationship now. Lol. You're a little late to the punch.

  • That is fairly sound advice but a lot of them seem to be attributes of personality types rather than any actual dating errors so I think a lot of leopards won't change their spots.

  • I didn't think I would agree with all of the mistakes, but I do. Kudos lol.

    Only thing I would say is that as far as money is concerned there's no way to really bring it up without the guy making himself look cheap other than asking her out in a way that sounds like "I'm going someplace awesome that you'd love. You can come if you want to!". That way when she says she'll go there is an assumption that you pay your own way. But if a guy specifically asks her out, best he can do is be playful about it and say rock paper scissor for who pays. That way you find out a bit about her personality and both people are less likely to rack up the bill. Other than that it's just hoping her ideas of money are similar to his.

    Personally I've gotten lucky, every girl I've dated outside of one were adamant about paying their way, splitting or even paying for me. But I got lucky.
    I know other guys that ate $300 bills. Eh.

  • Very good take.

    About going Dutch, the number of women who don't mind doing this continues to grow. However, the number of women who are offended at the idea of going Dutch continues to be a substantial figure. A number of my female friends and colleagues continue to tell me they are upset if they have to pay on the first date, to the point where merely suggesting going Dutch will result in a "no thanks."

    I have also been informed by female friends and colleagues that for a few, when they offer to pay for themselves on a date, it's not a sincere offer so much as it is a test to see his reaction to the offer. If he accepts, there probably will not be a second date.

    Yes, I know such women are a dwindling minority. However I believe they are still a substantial minority.

    To your excellent list, I might add don't make grandiose romantic gestures on the first date.

  • These are some excellent guidelines. Can't remember the last dating Take I read where I completely agreed. It's a strange feeling. LOL

    Anyway, point #1 is *so* key. I know some dudes are a little scared so they just kinda dip their toe in the water, doing the whole "let's hang out" spiel. Things are so much better when you're bold and say what you want, though! I mean, I don't want to "hang out" with the girl I like -- I want to DATE her.

    Bottom line: there's no ambiguity with how I feel about her, therefore I'm not gonna word it ambiguously.

    Good Take.

  • Wow. I must say when I read the title I immediately said "oh, here we go again, some entitled feminist..."
    but it was actually a good take and all very valid points. As you said, not everyone will agree..
    personally if I ask a woman out on a date, I expect to pay the first date. but I expect her to pay sometimes. If she does not at least try and pay during any of the first 3 dates, I do not ask her out again ever. I would never ever ever ever ever "go dutch". That does not belong in dating. but I think that is something you young people have come up with.
    "hanging out" lolololol... I don't understand young people but this was the most ridiculous thing I have ever heard of when I heard it the first time about a year ago. So group date? is that really a date? I agree 100% with you on that.
    I have a firm rule, esp since I do online dating, I never even say the word "sex" until the woman brings it up. That shows I am interested in her for more then just her pussy and tits. Even though those are way up high on the list. I am a firm believer that rule has resulted in me being laid much faster then if I had brought it up.

  • Overall another good take , a man needs to have a sense of his own value , which will breed genuine confidence... or get shot down !! I will never be dating again , being a single dad , I neither have the time or the inclination , plus I'm also realistic , no woman will want a man in my situation anyway , I made my choices & my children will always come first. Hypothetically , if I was on the " market " I think dinner is a big mistake for a first date , as it puts too much pressure on both parties , a " keep it light " short coffee date with strictly no touching & never mention sex at all during the date , I would be more than happy to pay , but will also walk out if she is a " phone zombie " or other big red flags !!

  • 1) specific
    2) significant in today's world
    3) unbiased
    4) practical
    In other words.. A 10/10 rating. Good luck my lady.. For further myTakes.

  • i have a problem with the 1st 2 and the last 1
    the hang out thing- it's pretty much a way to get her to show you're interested in her without putting yourself all the way. it's kinda confusing and definitely blurs the lines, but for guys, we generally have more to lose. most guys don't give a shit 1 way or the other if someone says yes or no. we'll just move on with our lives. girls, however, usually act differently. i won't say they're less sensitive towards rejection, but there are instances where being rejected wasn't so subtle. i've been in all of those situations. 1 where i was let off easy and 1 where i've just been basically chewed out. the 2nd isn't fun. and even when a girl thinks "things will stay the same", i've had instances where the friendship just pretty much dissolved. so you're kinda playing with fire

    the paying for dinner- that kinda goes with the 1st 1. it's not that we don't think a girl can foot the bill or anything, it reinforces that it's a date. trust me, if we're paying for a 1st date, it's usually not somewhere expensive and not gonna miss the money. and even so, if things go well, you can pay me back later with ice cream or some shit :D

    for the sex thing, I don't know about that. i mean 1st date, i wouldn't unless y'all are really vibing. with that said, it's gonna come up at some point.

    i mean she is technically doing her a favor. like, i wouldn't overdo it and i'm pretty even keel, but it's kinda a big favor. like, there's a massive discrepancy between girls getting hit on and asked out and how often guys ask girls out and not getting rejected.

    as per the last 1, i mean the point is trying to impress her. the point in asking someone out is telling that person you like them and showing them why they should date you. like, the person doing the asking already likes you, the goal is for the askee to like that person back. that doesn't mean you disregard yourself for her, but it's more about the askee at that point. it's like a job interview. you're trying to impress the interviewer and showing them why you should be hired. they're in the position of power at that point cause there's a lot of other options if you don't work out.

  • Another well written essay containing the correct advice in an easy to read, organized, concise manner.

    this describes how i feel about this take love. Thanks for posting it, i needed some real good advice and this was it.

  • I made a lot of these mistakes early on but have gotten better. I still thank the girl way too much at the end. I want her to feel really appreciated but I think I take that too far.

  • I think I have avoided all of the above things that you said.

    The last girl that I tried to take a shot at, and this was the first night I have known her by the way, first I asked if she wanna get a drink because we were already in the part of town where the clubs and bars are at, but I didn't force it when the place was too crowded coz it was new years' eve and she said she didn't wanna go and i didn't totally wanna go either, coz it was too crowded.

    she went home and pretty much the next text i sent her was, hey i am gonna watch a movie at home tmr night, you wanna come over?
    and she didn't say no but she said oh your place is so far away.

    and then i am totally cool with it and didn't push her or anything.
    haven't texted her since either.

    i mean, even though i have never really been with a girl, i have been through just enough and read enough online advice to know that, when the girl isn't down for it as fast or as much as I am, booohoooo, who gives a sh1t?
    I have other things to get on my life with.

  • can't argue with any of those "mistakes"

    the not making it clear that you are interested is a big big one. saying you want to go out sometime is a lot different than making clear that you have some sort of romantic interest

  • What's a nice way of phrasing "I want to take you out to dinner and Go Dutch"?

    • "Hey, did you want to maybe split on dinner sometime?"

    • Show All
    • @BeautifulMind59 Yes I treat it as a business transaction because everything in life can be boiled down to its basic elements. There's just a different currency being used and different parameters.

      Of course she's thinking the same thing I'd be surprised if she wasn't. The way I see it, a date is when 2 individuals meet and enjoy each others company with the intention of creating a relationship.
      All I ask from the girl is that she be self sufficient and have an awesome personality and I'll reciprocate.
      The extra mile is what I have a problem with. I want to be in a relationship of equals not one where one party does more than the other to gain his/her affection.

      The reason I asked what's a nice way to phrase "I want to take you out to dinner and Go Dutch" is because the delivery of an idea is important. I don't want to come off cheap. I know that I'm morally correct since I live by the golden rule.

      I see traditionalist dating as oppressive.

  • Regarding point #1, hanging out and going on a date have their similarities, with one big difference being the intention behind them. I agree that guys should be upfront with their intentions; if you want a date say so.

    Regarding point #3, as a guideline there are 4 levels of communication you could follow as you get to know a person more:
    1. Small Talk: includes remarks about weather, our immediate surroundings, and
    current events.
    2. Fact Disclosure: discussion of occupation, history, hobbies, etc.
    3. Viewpoints and Opinions: religious views, political stance, sports teams
    4. Personal Feelings: personal problems, concerns, sex stuff

  • I’m not a dating expert, I’m not a guru or a love scientist
    Lucky for you, you don't have to be any of those things ! and the last one does not exist (it's a scam)

    I do agree with the take, and haven't found anything I disagree with, what I think it really all boils down to is having fun, being respectful, being a gentleman and be yourself.

  • Generally speaking, it's good advice, but to anybody that wants to follow this list to the T, know that it should be taken more of as a guideline. Much depends on people's personalities, get past the fact someone in the world noticed you and get to know her before you lose your mind.

  • So, if I already "hung out" with my crush three times, how do I make it specific that I wanna take her on a date next time? (If I ever get enough courage to do that).

    • Ask her to go on a DATE. Simple: "Hey, so and so, I think you're really cool and really pretty so I was wondering if you wanted to on a date with me?"

    • Wouldn't it be weird to suddenly say "I think you're really cool and really pretty" after I've known her for like a year and a half.

    • I don't see why it would be.

  • This was insightful.

    Number one was a real eye opener.

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What Girls Said 5

  • I agree with all of these.

  • Very good take.

    But, honestly, I think you should include "asking to dinner" -- altogether -- in this list.

    Dinner is so... formal. It's so totes formal, and -- as we see right here, in this take -- it's so fraught with potential pitfalls, regarding money and so on.
    And, let's be honest here, it's kinda boring. Even if yr partner is an awesome conversationalist, (s) he will be an even better conversationalist in a more fun place, where his/her mouth isn't full of food half the time.

    Srsly, dinner should NEVER be a first date. Probably not a first or a second or a third date.

    Cheap eats at some place along the street? Sure, mb. That's a different animal.

    A dinner date should not happen until you already know the other person decently well -- and, specifically, not until you absolutely know EXACTLY how they deal with money and paying for stuff.
    If there's gna be awkwardness about that sort of thing, dinner is definitely the worst time to have it.

  • Penis complex is all they have in their mind

    • Why would you say such a thing. How can we as human beings move forwards if we don't learn to respect and say good things about the opposite gender. Fuck women today... sometimes i feel ashamed of my own gender

  • Maybe bringing up sex right from the start is not a good thing in general. It actually really depends on what both sides want. Girls, like guys, may want different things in different stages of life. Like, if I have a huge crush on a guy, I not only care if he talks about sex, I would likely be hurt if he didn't. Hell, screw talk about it, I would love if he just goes for it all the way, first base to third! I would be greatly disappointed if he didn't.
    And I would probably tolerate/prefer a slight hint or two at sex at my age, rather than the pure romance and butterflies I was strictly sticking to in my 20s when I was young enough to wrongly believe that sexual advances are bad news. So, basically try to read the signs. What does she want? How far is she willing to go? I know it's hard and it requires experience.
    Anyway, enough side tracking. The thing I was trying to say before getting side tracked is that a well designed compliment on a physical characteristic of a girl, said honestly and without dirtiness in your mind ONLY AT THAT EXACT MOMENT, is not only a safe bet, it will most probably win you a lot more than you expect.
    Eyes are a very good place to start. Or hands, or hair. DON'T do lips. And certainly not legs.
    I was at work one day, and this young man comes over to me in a not too busy not too quiet corner, and says in a way you would give a compliment to your best friend, with a warm and polite but not too radiant smile: "I hope this doesn't seem rude, but you have very beautiful eyes."
    I'm sure I would have dated him if I were single.

  • I definitely agree with all of these.

    If a man says "I want to buy you dinner" or "I want to take you to dinner" he better be paying. Don't tell me you're gonna buy me a horse if you expect me to pay for it myself.

    • Why can't you guys pay half and half. Go dutch. Where's the problem?

    • If one asks out he/she should pay. @MilkyAmy

    • @MilkyAmy splitting a check does not belong in dating. You can certainly take turns. but if you can't afford a dinner, then there are other things you can do on a date. Certainly it depends on where you live, the weather, and your age. If your really young, you may not have money. But no dad is going to refuse his son a twenty to take a girl out. esp a first date...