How should I ask someone out? Should I be more direct?
May 2, 2022 1:28 AM   Subscribe

I've been in relationships before but this is always confusing for me. My female friends tell me it's not any better on the other side.

I'm not real sure how to go about this, so I'll just ask.

Some people tell me I should just outright indicate my interest in someone if I feel attracted to them. As in, talk to a woman and ask her out immediately.

Other people, such as a woman I know has told me that's too forward and that she'd like to know someone as a friend before she commits to dating.

I've also found that you can be direct with someone and still get nowhere or that they won't clearly tell you whether they are interested or not. In the past I just don't bother if I get no answers but people have also told me that not everyone will be that forward and that I shouldn't drop people that fast.

I don't know or understand any of this. And sometimes I'm quite unsure of what to say or do when I meet someone I like.

I don't suppose anybody has any advice?
posted by anonymous to Human Relations (25 answers total)
 
If they won't clearly tell you if they're interested or not, they are likely not. Even if there is a chance they are, playing reindeer games like "guess if I'm interested or not, because I won't be straightforward" is a sad use of time and life.

If you like someone, ask them out. If you don't get a "[expletive of your choice] yes" reaction (https://markmanson.net/fuck-yes), move on. Don't you want to be with someone who is enthusiastic about you as you are about them?

If you "don't drop people that fast" when they are waffly, you'll end up perpetually being the one who is more invested. Yuck. At the absolute most, leave room for the idea that the person may come around, but if so, they'll now need to be the one who initiates with you.

if you're having trouble motivating yourself, imagine being on your deathbed. Will you wish you had played it more safe, or wish you had asked out that person you were interested in? Act as though life is short, because it is.
posted by Flock of Cynthiabirds at 4:06 AM on May 2, 2022 [7 favorites]


Setting matters a lot here. Approaching someone in a setting where they're probably socially open--a party, maybe a bar--is different from one where they're not, like the grocery store or the street. Are you talking about someone you've become attracted to just by looking at them?

It's not a great idea to stop someone who's going about their business to start a conversation with the goal to ask them out--at the very least that's an advanced move. Women especially are often turned off by this; it makes you feel like everyone around you is evaluating you romantically all the damned time.

If you're talking about a casual social situation, where you've been introduced or are already talking, or you're at a party or something where there's an expectation of meeting people and conversing, then yes, talking enough to get to know them and then asking them out is reasonable. Definitely follow Flock of Cynthiabirds's advice, though, and take anything less than enthusiasm as a "no."

Do not go straight to asking someone out when all you know about them is what they look like. That's a bad gamble and really objectifying.
posted by gideonfrog at 4:36 AM on May 2, 2022 [16 favorites]


I personally prefer for people to be open and honest right away. I have always been horrified at the idea that someone might befriend me when their real motive is to have a romantic/sexual relationship with me. I'm a woman, not sure that's relevant.
posted by RobinofFrocksley at 5:08 AM on May 2, 2022 [2 favorites]


I can only speak for myself and my own preferences. I am a woman. I am generally in favour of directness, but I think it's inappropriate to proposition someone immediately out of nowhere when you have absolutely no indication of their interest.

I become attracted to very specific men. If I am attracted to someone, I try to make preliminary overtures to try to figure out if the attraction is mutual. How directly I escalate the overtures depends on lots of things -- for example, how I know someone and under what circumstances I interact with them, and how awkward and/or uncomfortable our interactions could potentially get if I make a move and I'm wrong. Casual acquaintance seen occasionally in social settings? Easy mode; low risk. Someone seen frequently at a structured hobby activity? Orange light; things could get weird. Work colleague? Hard mode, and depending on the workplace relationship and office culture, very possibly a complete no-go area, regardless of how much I wish it were otherwise.

And I guess that's how I want to be treated in return. If someone likes me, I would like them to make some effort to find out how interested I am in them before they ask me out. This is a feedback loop, and it should go in both directions. There isn't a magical checklist, but in general I would say the kinds of signs to look for are: do I go out of my way to initiate and extend conversations with you? Do I favour your company over other people's company? Do I do this even though there is no explicit or implicit social obligation for me to do it? Is my body language open when I'm speaking to you? Do I steer the conversation towards more intimate and personal topics, or away from them?

I am an introvert who likes to be a hermit, so I would like to say that I make this relatively easy for other people, but I realise that some "signs" can be misinterpreted. If I'm into you, I will fall over myself to make concrete plans to meet you in person, as soon as possible and frequently. But if I make non-committal noises about maybe meeting somewhere sometime, after you asked, and never spontaneously follow up, I'm probably just being polite. I'm also a nerd, so if I nerd out animatedly over some shared interest in a conversation with you, I'm afraid that doesn't mean anything -- I do that with all my platonic friends.

As someone who is has been single for a couple of years after over a decade of being in a long-term relationship, I feel this awkward tension when interacting with some of my single male friends, because I worry that they're misinterpreting my friendliness or politeness as romantic interest, and I'm constantly trying to decide if I'm being too friendly and giving them the wrong idea. Which sucks.

One of them did in fact ask me out recently, and I declined. I'm not mad that he cut straight to the chase -- this eliminated a lot of awkwardness, now we're on the same page (although it's not the page either of us would have wanted to be on). We've known each other for long enough that if I were going to develop romantic feelings for him, I would have -- and I haven't, so I'm pretty sure it's not going to happen.

(If I don't feel attracted to someone, there's nothing that I can do about it. I don't need more time, and I can't be "persuaded". It's just not going to happen. There seems to be a popular model of attraction that ranks people on some objective scale and assumes that if you are objectively "hot enough" you can expect a positive response from people you approach -- and if you don't get that response, those people are suggesting that you're "not good enough" and are therefore somehow bad people. This is completely alien to my subjective experience; I think it's toxic, and I worry about navigating a dating culture where this idea has taken hold.)

I don't know how I feel about the idea that I would want someone I've just met to try to be friends with me before asking me out. Maybe this is just another way to phrase the "overtures" that I'm describing -- but the process I'm thinking of is done with romantic intent from the start. To me the "friendship" phrasing sounds worryingly like pretending that you want a platonic friendship when you're actually using the trappings of friendship to lay the groundwork to ask someone out. That sounds deceptive, and it's not something that I would enjoy being at the receiving end of.
posted by confluency at 5:10 AM on May 2, 2022 [14 favorites]


Since it hasn’t already been spelled out, consider people you meet in a work/professional setting off limits. Just try to not even evaluate whether you’d be attracted to them in other circumstances.
posted by Kriesa at 5:10 AM on May 2, 2022 [4 favorites]


There is no such thing as a right answer to this, just a right answer for you in the moment when you want to ask a specific person out. Some women like to be asked out with confidence straight away (to be "chatted up"), some women hate that. There's no "correct" way to ask someone out, although there are lots of wrong ways and lots of wrong situations, as gideonfrog has mentioned.

Being frustrated and/or resigned to failure is definitely one of the wrong ways, and your question seems full of those two feelings. Constant rejection, especially for contradictory reasons - "this woman didn't like the direct approach so I tried softly softly next time and still got rejected. what do they WANT?!" - can be soul destroying. Asking someone out is stressful enough without knowing there's a good chance you've going to get refused based on your previous experience.

Ultimately, asking someone out risks a rejection and that makes you vulnerable. When you are constantly rejected, especially when you're trying to do things "the right way", that vulnerability can turn to pain and frustration and eventually anger. But remember that women get harassed for their appearance on a frighteningly common basis, so their initial response to what you see as romantic overtures is often cautious and based on self-defence, especially at first. They're got plenty of experience of men and often that experience is not good.

That being said, it sounds like reading up on the Ask vs Guest culture dynamic would be useful here. Different people have different ways of signalling things and understanding that might help.

Slow down a little, find out if you like spending time with them rather than just looking at them, take time to try and read the signals (read and reread confluency's post), and work up towards asking them out rather than diving straight into it.
posted by underclocked at 5:10 AM on May 2, 2022 [2 favorites]


If it's a situation where not you're going to see the person again, ask them if they'd like get coffee sometime.

If you are going to be seeing them multiple times in the future, get to know them a little, then ask them out
posted by Brandon Blatcher at 5:12 AM on May 2, 2022 [12 favorites]


Some people tell me I should just outright indicate my interest in someone if I feel attracted to them. As in, talk to a woman and ask her out immediately.

Other people, such as a woman I know has told me that's too forward and that she'd like to know someone as a friend before she commits to dating.

I've also found that you can be direct with someone and still get nowhere or that they won't clearly tell you whether they are interested or not. In the past I just don't bother if I get no answers but people have also told me that not everyone will be that forward and that I shouldn't drop people that fast.


The problem is that all of these things are true. Some people would prefer to be asked directly (as many folks above have mentioned, probably in a social setting and not randomly on the street), some people would prefer to build a friendship first, and some people might not know what they want right away, and need a little time/discussion/flirtation to figure it out. You can choose one approach - but understand that you might be missing out on some potential dates that would prefer a different one. You best bet is to treat people as individuals and do your best to suss out their preference based on your initial conversation. Importantly though, as Brandon Blatcher says, do "ask them out" explicitly. "Would you like to get coffee sometime?" "Would you like to go out to dinner sometime?" etc.
posted by Rock Steady at 7:35 AM on May 2, 2022 [3 favorites]


“this is always confusing for me”

It always will be, dude. Sorry. My wife, to whom I’ve been married for nearly eight years now, still makes fun of how awkward I was when we first met. And that was a best-case scenario ask-out.

A lot of people have advice. There’s a whole industry that has sprung up to give people, especially guys, dating advice. Most of it is crap and you should ignore it. The best advice is to be yourself and trust your gut. As much as my wife makes fun of me for being awkward, she’ll also tell anyone who’ll listen that the reason she went out with me is because she could immediately sense I was being authentic and not playing games. That’ll get you further than any PUA BS.
posted by kevinbelt at 7:40 AM on May 2, 2022 [1 favorite]


It's super frustrating, but this varies enormously by the context and the individual, so there's no right answer.

If I meet someone out in the world and they immediately start chatting me up, it makes me run. Since they don't know anything about me, they don't have personal interest in me specifically, and that's a turn-off.

If we meet, have a nice conversation during which they act curious about me, we find some things we have in common and develop some sort of rapport/ chemistry, and they say, "Hey, I've really enjoyed talking to you; would you like to get together again?" then that would work for me, assuming I felt the chemistry too.

Unlike confluency, I sometimes develop attraction to someone over time if I like them but am not physically attracted to them initially, but only if we're hanging out in a non-romantic context while that grows. Again, each situation is unique so that doesn't provide any actionable data.

With online dating most of us are more open to moving quickly than with people we meet in real life; long periods of just messaging tend to lead to everyone getting bored and drifting off. Since we all are there for broadly similar things, once I've established basic compatibility, I like to meet ASAP.
posted by metasarah at 7:44 AM on May 2, 2022 [3 favorites]


Most people I know are meeting people on dating apps now rather than in encounters in real life, and that might be good for you since it's less ambiguous- both of you will know that the other is at least somewhat interested, and if you exchange a few messages and it seems promising, you can set up a date.
posted by pinochiette at 7:52 AM on May 2, 2022 [2 favorites]


Agreed that there is no right answer.

Another question to ask yourself: do you feel chemistry with this woman? Is she responding to your flirtatious gestures with some of her own? Then you can definitely ask her out, whether you've knowN her for years or hours.

*But*

It sounds like you're maybe a little confused on how to read whether a woman is flirting with you, which is a problem a lot of men have. You indicate you have some female friends who you are close enough with that you can talk about these sorts of things with - you might try having them around you in social settings like a bar/party so they can be your "wing woman" so to speak, to give you a second opinion.

If that doesn't work, I agree with pinochiette that dating apps are good for taking out some of the ambiguity.
posted by coffeecat at 7:57 AM on May 2, 2022


If someone likes me, I would like them to make some effort to find out how interested I am in them before they ask me out.

I worry that they're misinterpreting my friendliness or politeness as romantic interest, and I'm constantly trying to decide if I'm being too friendly and giving them the wrong idea. Which sucks.

If I'm into you, I will fall over myself to make concrete plans to meet you in person, as soon as possible and frequently. But if I make non-committal noises about maybe meeting somewhere sometime, after you asked, and never spontaneously follow up, I'm probably just being polite.


I second all of this.
(a) I haaaaaaaaaaaate having to say no to a guy. I really hate it and I'm scared to say no. I don't develop attraction later on. I would prefer that a guy figure out if I'm into him or not (sadly 99.9% of the time I'm not) before we have that awkward shitty conversation. This is probably more of A Thing for someone you see more frequently than a cold approach, though.
(b) Unfortunately, being generically friendly to a lot of guys does give them the wrong impression, apparently :/
(c) In the end, it's a "fuck yes or no" situation. If they say yes, or "I can't do that day but what about next Saturday," they are interested. If it's a vague no or "I'm busy" but no followup to schedule it for later, they're not interested.
posted by jenfullmoon at 8:24 AM on May 2, 2022 [4 favorites]


Fundamentally you're looking at "women" like it's a mysterious alien machine whose code you need to solve, instead of an enormous number of individual humans you'd like to get to know. This attitude is going to color any approach you use, whether it's direct or indirect. They're just people, my dude, same as you. What do YOU like? What do you like about your women friends? What do y'all talk about? Dating is just that plus chemistry/attraction. Literally, just be a person with other people, and this shit will work itself out.
posted by We put our faith in Blast Hardcheese at 8:33 AM on May 2, 2022 [10 favorites]


I've also found that you can be direct with someone and still get nowhere or that they won't clearly tell you whether they are interested or not. In the past I just don't bother if I get no answers but people have also told me that not everyone will be that forward and that I shouldn't drop people that fast.

I suggest that this kind of person is probably a bad match for you. You sound like someone who thrives on clear communication. You don't want to end up dating someone where you're always a little unclear whether she really enjoys what you put on the table. This is not you.

(Plenty of people enjoy trading more subtle signs of interest. That's not you. And it's okay.)

Don't be afraid of ruling people out who might be interested in you, but just don't fit well to you, to the extent that you have trouble understanding them.

The goal is not to maximise your number of dates, it's to date in a way that works for you.
posted by Omnomnom at 8:37 AM on May 2, 2022 [1 favorite]


If you're dating based on attraction, yes to initiate small talk > ask to get coffee / a drink > anything that isn't a clear yes is a no.

If you're more in a dating to marry/partner in a limited social group with underlying rules, then being less forward makes sense, you will see them again without making plans and the commitment involved in being seen as an item is higher. Women might be concerned that others will ask / interfere if you're dating or that dating too many people will negatively impact others' perception of them. It's a spectrum, meetups run pretty much the whole gamut of it, and different people in the group will also view the scenario different ways
posted by momus_window at 10:40 AM on May 2, 2022


Also, a corollary to not approaching anyone in a work/professional setting, that includes when it’s not your work, but it is theirs. Don’t act on any attraction to your accountant, bartender, doctor, grocery store clerk, etc.
posted by Kriesa at 11:09 AM on May 2, 2022 [4 favorites]


If you're generally a direct person in life, then I think it's probably better for you to be direct in expressing interest (assuming we are talking about a social situation and not a work or other professional context, where the woman you are interested in is a coworker or in a service industry role like a barista). If someone doesn't like that kind of directness, better to know that from the start.

As for your woman friend who wants to be friends with someone first: it sounds like that works for her, but that doesn't mean it works for other women. Also, if you asked out someone who was like this, she could say, "I'd like us to become friends first," right? It's not your job to read her mind. I'd find it awkward to know a man was spending time with me, as a friend, but really because he wanted to date me.

I agree with others who are saying there is not one answer here. There isn't a right way and a wrong way. What feels authentic and true? Do that, because you want to be with people who respond to you when you are authentic and true.
posted by bluedaisy at 11:22 AM on May 2, 2022


I don't suppose anybody has any advice?

Nobody else is any better at this than you are. The only thing you can do about it is apply yourself to becoming progressively better at not getting knocked off balance by uncertainty.

Other people's responses to you are not within your control. Responses from people you don't yet know particularly well but would like to know better are unpredictable exactly because you don't yet know them particularly well.

Ruminating on this issue in a doomed attempt to gain a sense of predictability or control that will only ever be spurious anyway can only ever make things worse for you. Give up searching for certainty and practise courage instead.

When it comes right down to it, if you take a punt and get it wrong then the worst possible outcome is an awkward moment that if you don't make a big deal of afterwards, then neither will anybody else.
posted by flabdablet at 11:56 AM on May 2, 2022 [2 favorites]


The challenge here is that women, like all people, are individuals who have different needs, preferences and styles, so there can be no One Pick Up Approach To Rule Them All.

That said I think there are a few general rules of thumb you can follow

Direct and respectful communication is always appreciated.

Context matters. If you might not get a chance to see/interact with this person again, don't let the opportunity to at least exchange contact info pass you up.

A direct approach should focus on getting to know the woman as a person and not simply a sex object.

Coming on strong if you just met someone gives off a creeper vibe you probably want to avoid.

If you are meeting this woman in a professional setting, treat her as a professional and not a romantic object.
posted by brookeb at 4:16 PM on May 2, 2022 [1 favorite]


You seem like maybe you have a kind of hard time reading flirtation social cues, so, before asking out any woman, maybe try to feel out her interest using these rules:

1. Do not flirt with anyone at your job. Do not flirt with anyone who's at THEIR job (server, etc).

2. Ideally, talk with her at least 20 minutes before asking her out. That 20 minutes can be added up over a few different convos. If it's hard to accrue 20 minutes, it might be a sign that she's avoiding you.

3. Once you've talked a few times, if it's possible, put yourself somewhere that she can see you, but don't interact with her, and see what happens. If you look at her, it's like "asking her" to talk to you, so don't make eye contact - look down at your phone or a book. See if she comes over to say hi. If she says hi to you first - when she's not being paid to be friendly! - then that's a pretty good sign.

4. In a group setting, when someone makes a joke, check who she looks at when she laughs. In "Group Laughs", people tend to make eye contact with the person they're most drawn to. Not always, but again it's a good sign.

5. At the end of a convo, ask her, "Are you on {social media}?" If you're both under 40 and she likes you, it's fairly likely she'll offer to friend / follow you. If she doesn't offer to connect on social, it's not a good sign.

6. Notice her body language when you talk.
Are her sternum and belly turned directly towards you? (That's a good sign).
Or are her sternum and belly turned away, and her shoulder is more towards you? (More likely to be a bad sign).
Are her arms crossed / is one of her arms placed between you two? (More likely to be a bad sign).
When you're talking, what part of her face is closest to you - her nose? (good, means she's looking right at you),
Or is her cheekbone the part of her face that is closest to you (bad, means she's subtly turning away from you).

7. To ask someone out, make sure you're alone. Don't do it in front of her friends. If she's with her friends, you can say "Hey can I talk with you a sec?" (don't pull her far away, just like over to the bar or off to the side). If she's reluctant to leave her friends, she is politely saying no, so just stop and back off and all is well.

8. If she does steps aside with you and you're alone, you could say something like, "Hey I wanted say, I've really enjoyed talking to you." Then notice her level of enthusiasm.
If she says "Yeah, me too" quite quickly and with her eyes wide and eyebrows raised, that's a good sign. Then you could say, "It would be great to talk again some time!" and see what she says.
But if she says "Oh yeahhh meee tooooo!!" in a high pitched or singsong voice, or with her eyebrows frowning or her eyes squinched (the way people frown at cute puppies when they say awwwww), she probably means "no".
Just stop and back off and all is well.

If you're still getting yes signals at this point, you can say, "I'd love to grab a coffee or a bite some time if you're up for it." Then you can exchange numbers, text her, and make plans.

If you get, say, 2 NO signals at ANY point, stop and back off. It's ok to lightly continue after one NO signal because it could be a fluke, but 2 is pretty unambiguous. Just stop and back off and all is well.
If you do this stuff right, it's all a subtle dance and by the time you get to asking someone out, she has told you in about 10 nonverbal ways that she's open to it.

If you are ever unsure whether a woman will say YES to a date invitation, it means you're asking too soon. You need to keep interacting and watching her body language for clearer signals that she is open to the ask.
posted by nouvelle-personne at 5:24 PM on May 2, 2022 [4 favorites]


I'm not always very socially normal, but normal is often neurotic:

I'm enjoying getting to know you.
If you ever wanted to ask me out for drinks/on a date, I'd say yes, but it's not an either/or thing, I genuinely like you as a friend.

And then never hit on them again. If they are interested, they'll let me know. If they are the sort of person who still wouldn't ever tell me they are interested even if I've let them know it would be welcomed, that's still OK, because that's not someone ready to be in a relationship with me!
Someone might not respond right away, they are getting to grips with whether they like *me* that way. That's cool. Meanwhile I've said my piece and dropped it entirely, which is great, because otherwise when one person has been crushing for ages, even if the other reciprocates at some point, often there's a real uneveness in built up attraction, which sucks. So say something early, but very low stakes, and then ball is in their court. Nothing goes further unless they serve the ball back to you.
posted by Elysum at 7:59 PM on May 2, 2022 [3 favorites]


In my observation, the only people that are good at this are those who have perfected 'pick up lines' with a view to getting to the sex part as soon as possible, without going through all that pesky intimacy stuff first. Real people, who want to get to know someone with a view to a relationship, always suck at it. Maybe not everyone, but it's definitely a minefield.

Despite that and my poor self-image and introversion, I managed to navigate my way through the minefield of on-line dating and ended up marrying a wonderful woman. I preferred meeting women online initially because it does ease the whole awkwardness given everyone there is looking for someone and there's no secret about that. Others here have pointed out only a tiny portion of the situations where it's not OK to pursue someone in real life and online takes some of that worry away.

It doesn't sound like you're doing the online thing but, if I were you, I think a similar approach is more likely to work - chat a little with someone, get a sense for how they see you (always remember that being polite doesn't always convey attraction and that women have to be guarded to be safe) and, when it feels like the right time say 'would you like to catch up for a coffee sometime?' because we know coffee is kind of a pre-date that doesn't come with the same level of commitment as, say, dinner and a movie (do only us old people do that these days?). It's harder with someone you may not see again and, in that situation, I would say that I'd be interested in talking to them some more and let them offer their contact details. If they don't, well, you got your answer.
posted by dg at 9:56 PM on May 2, 2022


This is a very minor point, but I want to clarify something I said which I think is misleading. My attraction to other people isn't always instant -- so technically my feelings can and do change over time. It's still relatively uncommon and beyond my control. I think what I'm trying to say is that if someone turns you down, it's possible that they'll change their mind, but you should leave the ball in their court and not expect that this will happen.
posted by confluency at 2:58 AM on May 3, 2022


There is one single correct answer, because there are at least two variables: your attraction to the target, and the target's attraction to you. Both are needed to build a relationship, and they can go up, down, and at different speeds.

The truth is somewhere in the middle. Be open and honest, but not too far, "I'd like to know you better. Coffee or juice after work?" If there's a hesitant reply, that's rejection. Move on. If there's at least some attraction coming back toward you, then the answer should be either yes, or a counter-offer ("How about tomorrow?") Anything else is a rejection.

Then you'll see how things go from there.
posted by kschang at 1:27 PM on May 3, 2022


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