Welcome to the Twenties: How to Ask a Guy Out

Why do many women simply drop subtle hints and wait for the men to do the dirty work? There is nothing wrong with a woman asking a man out! It may have been unimaginable in the old days, but times have changed, people.

Note: the following tips may help men who are trying to ask met out, as well.

The first time I asked a guy out was in freshman or sophomore year of high school. I'd just started to build up my identity and begun gaining confidence in myself. He was the most popular guy in the grade and I was one of the music girls. We were in all the same classes together. I fell for him because he was the smartest guy in the grade, played soccer, was fairly good looking, but most of all because he had a hidden musical talent his friends didn't know about. He was a great rapper and producer.

One day I took a deep breath, went up to him in the hallway, and asked if he wanted to "hang out sometime" on a double date. He said, "okay" but after a few days told me he'd changed his mind, because there was some girl who'd dumped him whom he was still hung up on. I was humiliated but tried to keep my cool. A year later, he came around and we dated for a bit.

Here in college, it's been much easier meeting people and being asked out on dates. However, I came to realize that I don't enjoy these dates as much as when I go out with someone I ask out. I'm sure there are ladies out there who feel the same.

Asking a guy out as a teenager and doing so as a twenty-something year old, I've found, are quite different. We're not kids anymore. In high school it was, "You wanna-?" or "I was thinking we could-." "We should-". Otherwise, we'd wait for a guy to ask us. But as a girl who has more guy friends than girl friends, I've learned from the guys that that is NOT how a grown-ass woman asks a guy out. Take notes, ladies.

Here are the big no-no's:

1) Making the date sound "casual" so not to scare him away.

Don't do this! It may have been cute in your teens but not anymore! If you ask him like it's a simple hang out he will assume you just want to be friends. It won't be a date at all. MEN don't get subtle hints; you have to be direct. If you're into him, show him you're into him; don't pretend you're not.

2) Dropping subtle hints and expecting him to do the dirty work.

It's not a man's job to ask the girl out! If you find yourself "waiting" or anxious that he'll slip out of your fingers before you could have a chance with him, ask him out yourself! There is nothing to be afraid of. If you have good taste and the guy is a gentleman, he will most likely say "yes" even if he isn't (yet) into you. Otherwise, he would decline politely. If he's a jerk about it, well, be thankful that you didn't start dating a douche like that.

3) Asking a friend to ask him whether he's into you before you consider asking him out.

Okay, I admit I did this not long ago. I did it knowing it was stupid. But never again! We're not twelve! It doesn't matter if he isn't into you. So ask him out, get to know him and allow him to get to know you. How's a man supposed to decide whether he likes you if he doesn't even know much or anything about you?

4) While asking him saying, "-but it's okay if you don't want to!" or "-but no worries if you're busy!"

Be. confident. Don't take no as an answer - unless he's taken, his mind is full because his mother just got carried to the hospital, because he just broke up with someone, or because he's gay. A grown-ass gentleman says yes if he has no reason to decline. A date is not a declaration of a relationship or marriage, it's simply a chance to get to know each other and have a good time.

Now here are the yes's:

1) Making sure he knows it's a date.

Use classic lines like, "would you like to have dinner sometime?" "Would you like to go on a date with me?" "We should go out sometime. Like on a date." "If you don't have plans for Friday night we should have dinner together." (That one may be a bit too subtle) "Have you ever been to ___? Would you like to go there on a date with me?"

2) Being confident.

Don't be shy or sound shy. Men like confident women who're sure of themselves. Know how you're going to ask him, go up to him, give him a flirty look in the eyes and go for it.

3) Not expecting too much from him.

Don't burden him in case he's not into you (yet). Don't make a bunch of plans for things to do on the date; do something simple. Because if he's not interested (yet), all that "stuff" will just sound like a lot of work and he won't want to go out with you. Just make it a simple meal, a fun time at the carnival, or going to an art gallery. Don't be all, "I always wanted to go to that thing where we write our names on heart-shaped paper and stick it on this large wall where other couple stick their names..." No.

4) Before you go on the date, plan some topics for discussion.

Do some background research. What? He won't know. Check out what he's into - hobbies, sports, food, etc. If he's from a different culture, do research on his culture. Any points on table manners? Cliche topics you shouldn't bring up? What's famous in his hometown/country? What's his passion? What do you know about it?

LASTLY, here's something I'm still trying to wrap my head around. Apparently guys don't really understand when women dress cute on the date... (???) The guy I last went on a date with was like, "you look nice. Any reason?" In my head I was like, uhh why are you asking me that? You know this is a date. I mean, he was dressed nice too. I ended up lying that I had work afterwards so I wouldn't seem desperate - but that may have been a mistake! I don't know. This actually happened to me a year or two ago as well. So, men (or women), any insight on this? Why would he ask me that?

That's all I have for you girls/guys. Happy dating!


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Join the discussion

What Guys Said 39

  • Hopefully plenty of women (and men, I guess) read this if they're struggling with the whole "do I ask this guy out? I shouldn't have to, I'm a woman!" dilemma. This is a mindset I see quite a few women holding onto, and it just doesn't make sense anymore, especially with the female empowerment movement encouraging girls to go after whatever they desire, and feminism as well. To put it plainly, women don't get to sit back and relax while judging men on their bravery or lack thereof anymore, it isn't up to us to do everything for her. I imagine plenty of women have missed dates with some really great guys by not making the first move and letting her interest be known in ways that are not subtle hints. I can definitely confirm, as a guy, that these hints don't really work at least not 100% of the time. There's been a few times where a girl has hinted towards something and I didn't realize what exactly she wanted until days later when I recalled the situation. By then, it was too late.

    I also think that sometimes, a girl just has to make the first move before a guy really knows she is interested in him, and from then on, he would probably be initiating more often as well. I have seen girls discouraging women from initiating by saying that if she does, he's going to be lazy. I don't think this is the case, a guy isn't going to let a girl do everything if he is actually interested in her, but we do like for her to show interest back by also initiating.

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    • I can definitely relate to realizing too late when a woman showed interest and failed to capitalize on it. Makes me feel dense, but then again, you never really know if a woman is just being friendly or she is attracted and is looking for more (date). I suppose that is why in the end, both sexes need to risk rejection and suggest a date regardless if we know for sure if there is mutual interest. It is hard for me since I am shy, but I hope one day I can work my way up to be being more assertive when it comes to sparking conversation and asking for dates.

      I know I wouldn't be lazy if a woman approached and introduced herself, started a conversation and showed interest. I'd still pay for the early dates, suggest dates, go for the first kiss when it feels right, etc.

      But I also agree that when a woman shows clear interest it is very sexy and shows that she won't be afraid of being passionate in the relationship. When a woman takes risks too it shows she is willing to be vulnerable.

    • Exactly! One of my girl friends once told me that I should never be the one to ask a guy out, or else they'll take advantage of my feelings. I'm glad I didn't listen to her! Now that I think about it, I really would have been dumb to listen to her because she's never been on a date. :P

    • I think for women it depends on what kind of man they are looking for. If a woman likes an intelligent, introverted, thoughtful, deep, sensitive kind of guy who might have some geeky or creative hobbies, then approaching a shy or more reserved guy might be the best way to meet someone like that. On the other hand, if a woman likes a more bold, brash, outgoing, charismatic type of guy, then it is probably best to wait until that guy comes along. I'm guessing both types of guys have a chance at being Mr. Wrong or Mr. Right, both can have the chance to be a user, immature, lazy, inconsiderate, clingy OR could be kind, caring, funny, loyal, and all the awesome traits you are looking for.

  • 6d

    Ugh. >.<

    "men don't get subtle hints you have to be direct"

    This is just code for "stop trying to manipulate people and actually be up front and honest with another human being for once in your life".

    It's not that men don't understand subtlety by and large, it's that we don't have the same maze of mental gymnastics in our head that we have to contend with. We're straight forward and up front about what we want and we'd ideally like it if everyone else could do the same, it makes life about a billion times easier than having to parse everything.

    If you actually look at the rest of your advice it just proves this point, you can sum all of this up by simply saying you should be honest, up front about what you want and direct. Instead of trying to manipulate the situation to get what you want.

    If you're dropping subtle hints to try and get him to ask you out, you're just manipulating him, just knock that shit off, men don't like to be manipulated.

    If you want to ask a guy out you have to do exactly the same thing men do which is you have to make yourself vulnerable by putting yourself out there and just asking honestly and maybe you'll get rejected and maybe it'll be the best thing you ever did, you'll never know.

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  • "It's not a man's job to ask the girl out! If you find yourself "waiting" or anxious that he'll slip out of your fingers before you could have a chance with him, ask him out yourself! There is nothing to be afraid of. If you have good taste and the guy is a gentleman, he will most likely say "yes" even if he isn't (yet) into you. Otherwise, he would decline politely. If he's a jerk about it, well, be thankful that you didn't start dating a douche like that."

    This is the philosophy I need to get ingrained in my head. Being a shy guy, this is the best kind of advice, just if the roles are reversed (man approaching woman). I think both sexes should be braver and approach each other, be more open to being approached, to show more interest, be more friendly. Shy men should hope for women to approach, and shy woman shouldn't hope for men to approach.

    I just know that it has to be difficult for shy women because men are a bit more intimidating in some cases and society, while it is changing, still generally lives on the tradition that men should be the aggressors. Although I don't see why starting a conversation and showing interest has to necessarily be seen as "aggression" or "assertion". If there is a good chemistry, the guy may still ask you on a date even if you introduced yourself first.

    At the same time, as a shy person, I want to be able to risk rejection and not be so anxious too because it can lead to more friendships and less missed opportunities in life in general. I think understanding shy people, of both sexes, is a great way to allow them to safely get involved with other people and to know that they just want to be accepted and loved just like everyone else. That there is nothing to be afraid of, nothing to be insecure about. I suppose there will always be those people who taint the waters with their negativity (creeps, abusers, jerks, etc.), but the more positive we make the experience for everyone, the better! More education leads to less creepy behavior, leads to more awareness, leads to more connection!

    Thank you for this Take! I hope more women AND men connect with one another and treat each other with respect.

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    • *Shy men SHOULDN'T hope

      Also, I don't really get why your date questioned your attire either. Maybe he thought you looked too sexy for the first date? I think that idea is absurd, but whatever. The right guy is going to appreciate you getting dolled up for any date, first or not.

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    • Weird. Maybe he didn't mean it to come out that way? If he did, I can see why you'd be befuddled.

    • Yeah, maybe he didn't mean it that way. All the times I saw him before I would dress super casual, maybe that's why. But still, it was a date and he knew it was... weird

  • 2d

    I think most women are totally capable of asking a guy out and I have a feeling that in the past many women did indeed ask guys out.

    I feel like nowadays a lot of women put WAY too much emphasis on what others think of them (social media effects) and can't fathom the idea that ONE man might not be into them.

    As to your question: my guess is that he may have been shy and blurted something out out of a loss for words. I've done that when I was flirting with girls when drunk (and younger). Or it may have been some sort of test (if he was a more experienced guy)

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  • Good take, but don't overdo it.

    There needs to be some mystery and games, otherwise you just come across as desperate and that turns nobody on (apart from desperate guys).

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  • Personally I don't like to dress up to go out. I don't like "dating" because it feels too fake to me. Dressing decent is enough. I want to know the real person. Whatever a woman does do not ask a guy what he does for a living. Because he will think you want to date him because he makes a lot of money.
    I think men should ask women out but a lot of women complain about harassment or men being creepy so in that case it's better for a woman to at least approach a man. Also make sure he is single because there's plenty of men and women out there that won't tell you unless you ask. I had a friends with benefits with a woman and she ended being married but I never asked. If you really like him try sitting beside him instead of across from him.
    I really like your post because you didn't make some excuse or not take accountability for your past action. On 2nd date I suggest the movies and if you really like him you can lean your head on this shoulder which is a sign that he can put arms around her.

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    • Thank you for your comment. It helps a lot. And a movie sounds like a good idea!

    • Your welcome, women like you are in the minority.

  • I admit, I’ve only read the last part. And that’s what I want to address. From my own perspective, in my own framework of beliefs.
    Guys don’t really care that much about what you’re wearing. They don’t perceive what should be “cute” or “nice”. It’s like (warning: wild guess coming) you and computers. If I’ll tell you Titan Z and Titan X (pascal), then you have probably not idea what I’m talking about. You don’t understand, absolutely not orient in this topic. The same is for guys and women clothing choices. We just don’t know. And more, we don’t care.
    So, I would add another no-no: getting offended/upset about this.
    Besides, if girls wear nice clothes, then…I don’t know if it’s because of me. What if there are other reason? Or I don’t even know, what am I supposed to categorize as nice. Do you see now?

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    • Interesting... So, even if a girl dresses nicely for a date guys don't get why?

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    • I see. Thanks for your comment! I'll keep in mind that what we do on the date is what's important.

    • But take with that disclaimer.
      It's from my perspective and other people are different.

  • 5d

    In 98 when I was 18 my gorgeous girlfriend of that time walked right up to me and said 'I like you and I think you like me so you want to start seeing each other.' It's not new it just takes confidence a lot of women don't have. She had shedloads of the stuff

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    • 5d

      Wow, I like how she said it!

    • 5d

      So did I. I'd been watching her all week and thought I was being sly about it. I was as obvious as the sun on a clear day though. Everybody knew. Thank God she asked

  • There must be more to the question of why women don't ask men out that has made this question endure so long. Seriously, my parents were asking the same question when they grew up. You would think it would have been standard practice by now if there wasn't some intrinsic reason why it doesn't happen much. Personally I believe in roles for men and women and that it's a man's job to court a woman. I think that it's nature. And natural behavior doesn't always observe the politically correct rules du jour.

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    • It's interesting you see chivalry as "nature". Thanks for your comment!

    • You're welcome. Thank you for the opportunity. Maybe we view it as chivalrous because we understand that it comports with nature rather than the other way around. So maybe we see natural behavior as chivalry.

  • 6d

    FUCK YEAH! I LOVE CONFIDENT WOMEN, WHO MEAN BUSINESS!!! 👩👩👩

    i agree with most of these things but i would still advise to not pressurize guys (for example not taking no as an answer as you mentioned) when it comes to asking them out ;)

    Also it's okay to ask guys out to hang out with them. There is nothing wrong with it. But your suggestion is pretty initiative. Both will work :)

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  • Good advice and I hope more girls become more like you.

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  • It would be awesome if more women were like you.

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    • Thank you :)

    • basically unless i am extremely lucky when i try again, the only way i'm going to have a relationship is if the woman approaches me first.

    • If you want a woman to approach you, you should be friendly and approachable :)

  • 3d

    This right here. If there's one bit of advice I always give, it's be obvious with the guy you want. If he didn't approach you but you want him, ask him rather than waiting around for him and make sure he knows it will be a date. Good to see a girl has figured this out. We're not mind readers.

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  • 6d

    Awesome work. Most women need to work on it. They are just too shy and lose good opportunities.

    Opportunities don't come by their own, you have to bring them by your efforts

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  • 6d

    I really like the (yet) part becaues a lot of times im pretty slow on the hints. Its like a game of catch you can't throw a curve ball while im not looking.

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    • 6d

      Thanks! Just threw the "yet"s in there because we shouldn't be pushy if the other person hasn't decided whether they want to pursue you.

  • well said, wish more girls were like you

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  • Thank you

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  • 3d

    I agree so much with you! Really! I don't understand myself why we practice this age old practice when most of the old age practices are obsolete these days?

    Strange!

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  • Thank you. Sorry for answer to question, I don't mean it to sound insulting to you, but to boyfriend at that time. Find boyfriend who has a clue, Always felt following to be true about girls but I imagine it applies to guys as well; women are sexy because of the beauty of what is between their ears as much as the beauty of that which is between their legs,

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  • More from Guys
    19

What Girls Said 14

  • 7d

    Only asked my boyfriend out, if he had said no I would never do it again. Plus both sexes don't want do it cause they fear one thing: rejection.

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  • Easy.
    Step 1: Walk up to him.
    Step 2: Say "Hey. I'm interested in you. Wanna go somewhere?"
    Done.

    & if I had to guess he wanted confirmation that you did it for him to be assured/feel good about himself.

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  • 5d

    Nice Take

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  • It's a good idea for women to find the men they are interested in and seek them out. If you wait for guys to come to you you will have to wade through a lot of riff raff. That's how I approach dating- just go for the one you want.

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  • Basically - shy people are screwed. Sorry but these advices "don't be shy" are on the same level as "stop being poor" or "stop being depressed" and don't help people at all. The rest are on point though.

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    • At least shy girls get asked out time to time, no girl comes up to shy guy ever.

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    • 7d

      In all honesty shy is essentially a nice way of saying that someone has bad social skills. Don't compare being shy to something as serious as being depressed. Even the most outgoing people get nervous and insecure. With practice everything becomes better. So practice talking to and approaching new and unfamiliar people and building your social skills.

    • 5d

      Before I started asking guys out, I'd never even imagined doing it. but then I fell hard for this guy who wouldn't notice me. it was the will of wanting him that gave me the courage. Shy people don't have to be shy forever.

  • 3d

    I don't wanna become an adult.

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  • 4d

    outgoing eating

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  • 5d

    I think its cool to ask a guy out, but i think its much better if you know how to approach guys, going slow still the best way to build bond together...

    Get to know more, but of course, dont send the wrong signals, always let him know that you were not friends

    I think its also a big pressure for men, when they date girls they dont have any information about anything

    and of course, most the problem is who's gonna slip the bill with date.

    Maybe its better if you could talk about it first. And in the get to know stage

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  • 6d

    I'm keeping things old fashioned, i do better that way. Then again I am a traditional girl.

    As for him saying you look dressed up, perhaps to him it was overdressed in the setting you were in. For example a nice cocktail dress at some rinky dink hole in the wall burrito restaurant. Or a mermaid dress while ice skating.

    It's also possible that he's just a low maintenance guy and is use to the T shirt and jeans kinda girl

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    • 6d

      I don't know, maybe. But there, most girls my age are pretty fashionable. And I thought French guys really care about girls' fashion... Maybe because he's a country boy.

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    • 6d

      Well, Thanks for your input!

    • 6d

      Np 😊

  • I'd never ask a guy out lol

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    • You don't have to feel pressured to, but if there comes a time when you really like someone but he doesn't seem to notice you, know that it's probably better to speak up.

  • I do think it is ok for a girl to ask a guy out and vice versa but there are a lot of factors for most people, especially for those who are afraid of rejection. Here are the tips that worked for me:
    1. Make sure you kind of already built a rapport or know the guy/girl already. I knew him from grade school and also we facebook messaged each other for a few months.
    2. Really make sure you both are single and ready for a serious relationship. I made sure I asked him "ARE YOU SINGLE?" and he said "yes, been single for the last 6 years"... that's a GREEN flag.
    3. After you guys already talked for a few months and also know for sure you are both single and ready for a serious relationship then one of you can just wing it with the, so you want to hang out some time and grab some coffee? Yah, it can be the guy or the girl who asks that. I asked him if he wanted to hang out and catch up on old times, he said yes but he didn't have a car. I had to drive 4 hours to go see him.
    4. Once you see each other take another couple of weeks if not months to see if you are comfortable and get along. So once we were seeing each other on dates consistently then I asked him "so do you like me? Do you want me to be your girlfriend" and he said yes (by that time we were spending all our holidays together and our facebook status was in a relationship along with everyone of our family and friends knew we were together).

    So just take it slow, and go with the flow. Don't force anything. Kind of just allow it to happen slowly. If it doesn't happen then just move on, there's a reason why they said no and you can so no to people too. There's just no connection and no vibe. good luck

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  • It's all fine and good to say it. But do you take your own advice?

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    • Of course. Everything I've written is based on my experiences.

  • Great

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  • Fuck the "times have changed" bullshit. Traditional all the way! Until women make more money than men do, they need to continue to ask the woman out AND pay for the date.

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    • What the hell are you talking about? A lot of women DO make more than the man. That "women are paid less than men" stuff refers to STATISTICS, not every individual man and women. It is quite common for a pair in which the women makes more than the man.

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    • 7d

      @blueguy932000
      She is an example of why I went MGTOW monk.

    • 6d

      @cth96190 I'm not gonna lie, I had to look up what MGTOW means, but I can see why you chose to. Personally, I still want to get married and do the whole family thing, but we'll see. It just seems like the sweet girls get taken so quick that I don't have a chance. I would rather be single than with someone that I have to settle for.

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