Positive examples of flirting?
September 8, 2016 5:13 AM   Subscribe

MetaFilter regularly features negative examples of what men should not do when approaching women (for example, stories from women who work in the service industry who have to fend off advances by men who have confused good customer service with attraction). I'm looking for positive examples of how flirting and asking people out should work.

Thanks to MetaFilter and some awesome female friends who have been willing to share their frustrations with me, I am pretty regularly exposed to what not to do. That combined with my own religious background and social anxieties have made me (straight male) really nervous about approaching women. I basically don't know how to flirt.

I mean, I've seen read that SIRC Guide to flirting, but that's more of a manual, a list of instructions divorced from how real world social situations actually work. I want to hear stories that illustrate people doing it right.

Personal anecdotes are great. I'd love to hear stories from women of being approached in ways that made them feel good. Fictional depictions are also good (as long as they are realistic).
posted by JDHarper to Human Relations (39 answers total) 28 users marked this as a favorite
Check Dr Nerdlove.
posted by brujita at 5:39 AM on September 8, 2016 [4 favorites]

Here is a thing that a lot of men who I have met do not seem to understand. I would almost certainly not consider going on date with you unless I know at least a bit about you. And I say this as someone who has, like a lot of women, frequently been asked out in such a way as it's either the first thing the guy says to me, or comes up pretty damn quick.

I mean, the "why" of that seems obvious, but maybe it isn't - guys assault you, they stalk you, they say weird stuff about or to you if you don't turn out to be like they imagined you'd be, and I'd experienced most of that before I was out of my teens. So mainly, I want to make sure you're not likely to do any of those things before anything else.

Why am I lecturing you on this when you asked about flirting? Well, because I think lesson number one when it comes to flirting is, don't assume that it's right to start doing it until you have allowed the woman you are talking with to figure out a bit about who you are.

Real Life Examples: well, I've dated guys who off the bat made me laugh a lot (top marks, excellent way to flirt, I cannot resist someone who makes me laugh), and guys who had a particular thing in common with me that we could talk about and work on together and then flirting happened. But the guy I just married (woo yeah!), well I don't think we flirted at all. I think we just talked, and talked, and talked, about all sorts of cool interesting stuff, and then suddenly kissing seemed like a another really fun thing that I wanted to do with him too.
posted by greenish at 6:00 AM on September 8, 2016 [63 favorites]

This isn't quite what you're looking for, but I just want to say:

For me, there was none. It wasn't personal. I wasn't interested in being hit on, period. (I'm not available right now regardless, but I'm describing the situation when I was single). The most charming flirting still left me feeling uncomfortable and trapped.

With someone like me, the best case scenario is simply to probe very lightly, and then to accept my signals of disinterest and lack of encouragement and back off. The sooner you get the hint, the better.
posted by Cozybee at 6:08 AM on September 8, 2016 [14 favorites]

No flirty approach in the world would ever work on me or make me feel good. My spidey-senses know when a compliment is given with strings attached or an end game in mind, and no thank you.

IMO flirting is for fun; meeting/dating/getting into a relationship with someone requires authenticity. If you want to approach women to date them, be genuine. Save flirting for your friends, the person next to you at the bar, any person to share a moment with. Flirting is its own reward, and you'll find it easier to do and more natural if *you* don't have any expectations attached to it.

FWIW a lot of hetero woman-to-woman social interaction could be seen as flirting if genders were masked. Positive women build each other up, gently tease each other, touch each other's hair or the fabric of their sweater, etc. There's no ulterior motive there though, which makes it easier to accept and reciprocate.
posted by headnsouth at 6:16 AM on September 8, 2016 [30 favorites]

headnsouth articulated something I didn't know I wanted to articulate! a lot of what I say to my friends/women I've never met could be construed as me hitting on them, except that I'm not. I'm just delivering sincere compliments/gentle ribbing. it helps that most people know I'm married. but maybe worth doling out some positive feedback to folks near you (male and female) with no strings or expectations attached. it makes people feel nice to receive compliments, and it's good practice.
posted by lizifer at 6:29 AM on September 8, 2016 [4 favorites]

For me, the most effective flirting was stuff that didn't look/feel like deliberate flirting. Flirting, to me, is a lot of physical/appearance based stuff. Touching, eye contact, compliments, etc. Maybe it is insecurity, but that kind of flirting, especially compliments on my physical appearance, are a turn off. They feel forced and insincere.

If you want my advice, your goal isn't "how to flirt".

Your goal is "make a connection".

I honestly think the best thing is to go out seeking FRIENDSHIP. The best relationships (in my opinion) are just awesome friendship with sex. So go about it as if you were interested in being friends with someone. Make it be about their personality rather than their body/appearance. So my advice is conversation. Talk about stuff. Interesting stuff. Show you are able to engage in intelligent conversation. Listen to their responses and opinions. Validate that you see them as an intelligent human being rather than just pretty eye candy (which is my problem with "normal" flirting). I truly feel your way through is to engage the person intellectually. Once you're talking for a while and the conversation is going well you can toss out an invite for coffee to "chat some more".

True Story: My (now) husband more or less asked me out via a conversation we were having about movies and which ones are cult classics but actually crappy. I said that Pulp Fiction is a cult classic I could never get through, thought it was terrible. He said, "Well, that is tragic since that is a great movie. We clearly need to watch Pulp Fiction and then discuss why you didn't like it.". Bam. Movie date. Of course we actually ended up having our first kiss a few days before we had planned to watch the movie by accident (long story) but yeah.
posted by PuppetMcSockerson at 6:43 AM on September 8, 2016 [26 favorites]

The only flirting I've ever really appreciated was from people with whom I was already somewhat friendly. Sometimes with platonic friends in a fun way knowing it's not even intended to go anywhere. Never from strangers.

I met my husband on OKCupid, and we'd had a longish correspondence before we even met, which established comfort.
posted by Kurichina at 6:58 AM on September 8, 2016 [4 favorites]

Flirting with strangers is a spontaneous and joint thing, not something you can plan to do to someone.

Most flirting is within an existing friendly relationship.
posted by so fucking future at 7:03 AM on September 8, 2016 [9 favorites]

When I met the beau, it wasn't really flirting, it was just talking. We were playing a card game together at a social event, so we were already primed and prepared to meet other people. So after we played our card game, we just kept talking, and kept talking, and kept talking.

I was pretty smitten at that point, but we didn't actually go out for a few more weeks, until we kept bumping into each other at social events, and kept talking, and talking and talking.

It was about 2-3 months of running into each other in our various social circles before we had what could loosely be called a first date, and we weren't really in a relationship for another month or two after that.
posted by PearlRose at 7:09 AM on September 8, 2016 [1 favorite]

The only kind of flirting I like and respond to from strangers is when someone makes a quick quip about something situational (and not about me/what I'm wearing, etc) without expecting any sort of feedback from me - going back to watching whatever is happening or reading or whatever, and then a quick smile back. I know, this is very specific, but it hits the right notes of: not being threatening, not pushing for more attention, allowing me to ignore them completely without feeling guilty/worried they'll attack, or allowing me to follow up without pressure. Basically, it puts the ball back in my court to keep engaging. Sometimes it doesn't even need to be clever - a quick observation or comment has also worked. And then, if we start talking, they stay respectful of my space and let me initiate hints about wanting to see them again.

It's a bit different for people I see more regularly - with those, flirting comes after getting to know a bit more about them.
posted by umwhat at 7:20 AM on September 8, 2016 [9 favorites]

So, like lots of people have said, basically, "cold calls" for dates are problematic and usually not attractive to women. Both times in my life I said "yes" to dates with men I did not know but had only casually flirted with after meeting once, they displayed no respect for my boundaries on the date, with both trying to have sex after I'd said "no" and one, ultimately, raping me. So. The idea that you're going to approach a woman you've never met before or don't meet through friends with a good tactic for flirting that leads to a date is probably not realistic (outside of obvious situations like OKCupid or SpeedDating where people are explicitly looking for dates).

So, realistically, a total stranger on the bus who seems attractive to you is someone it's going to be very hard for you to date. Maybe you can strike up a conversation--probably not--and maybe you can mention some sort of public group thing you're going to be at that maybe she'd like to go to also and maybe you'll see her there. But that's not an approach with a high success rate with people who are not big on going to places/social events where they don't know anyone.

Someone you see at the same coffee shop every day before work, or someone who goes to your gym, or whatever, you get to know her just like you'd get to know someone you don't want to date first, then you flirt, then you ask for a date. Treat her like a human being who has no relation to any goal of yours. Then if it turns out you've got something in common or a spark, you suggest a date.

Just introduce yourself, make small talk, don't overstay your welcome, and expect to have several non-date-goal-directed conversations over the course of some months before you ask her out. Give her your twitter handle or instagram account or some way she can contact you without an immediate expectation of reciprocity and not a phone number which assumes too much familiarity.

Women are just people and you're going to have the best results forming relationships--whether dating relationships or just friendly ones--if you just treat them like people, not potential dates.
posted by LeeloDallasMultiSocks at 7:48 AM on September 8, 2016 [10 favorites]

I want to echo most of the above: flirting is a mutual thing, borne of connection. Not something you can impose on someone. Not precise steps you can memorize, because everyone is different.

We can tell when you're just talking to us because we are female and you want to have sex with a woman, any woman. Most women deal with feeling like a blank woman-thing/receptacle for male fears or desires multiple times a day.

So, given that, am I opposed to men I don't know talking to me? Absolutely not! Examples of times that have gone well (not all resulted in relationships or dates but some did):

-waiting for Chinese take-out. We'd ordered the same thing and were waiting a long time. He made some comment about how awesome the dumplings were so he'd wait an hour for them. I responded and conversation flowed.

-stuck subway train. He expressed mild frustration but wasn't ragey. We started talking about our commutes, then our jobs, then just bullshitting, and conversation flowed.

-bar. Both at the jukebox and he made some slightly teasing but positive comment about my selections so we started talking about music, then conversation flowed.

What are the commonalities?

-These all started out friendly, like two humans of any orientation talking about the world around them. Maybe they thought I was attractive but they didn't zero in on me like prey.

-They didn't go straight to flirting--they interacted with me so there was something about ME as a human that they liked, other than my anatomy.

-Positive, light, not desperate or pushy. Would have been okay if I hadn't responded at all which is KEY. Most people don't like being put on the spot.

-FLOW. A natural conversation. Can't force this one. Do you get along with and enjoy talking to everyone in the whole world? Of course not! Sometimes there's just no connection and that's okay. When there is one, these things tend to flow naturally, even for shy or awkward people.
posted by kapers at 8:06 AM on September 8, 2016 [38 favorites]

Thoughtful and attentive listening is the best flirtation technique I've experienced. My boyfriend was so good at listening on our first date that it completely superseded his obvious nervousness, and the fact that the date ended abruptly as he ran away to find a bathroom. It still remains one of his sexiest traits.
posted by Owl of Athena at 8:09 AM on September 8, 2016 [2 favorites]

I think a clarification will be useful here, are you trying to learn how to flirt appropriately? Or are you trying to learn how to get women to go out with you appropriately?
posted by corb at 8:12 AM on September 8, 2016 [5 favorites]

I think many men struggle with trying to figure out the appropriate way to flirt with complete strangers. It's impossible to do this without it ever being unwelcome. And decent humans, such as yourself, will try to do it in a way to do it in a way that will reduce the number of people you approach feeling uncomfortable. And then maybe feel an anxious tension because this reduces the number of people you approach, and potentially the number of people who, say, agree to go on a date.

However. I don't think it is necessary to approach total strangers ever.

Think about people you know in your life. Almost all the people I know my age in happy relationships met their partners through either shared activities (classes, clubs, sports teams, mutual friends, workplace) or online dating. Not through someone hitting on someone random just trying to get through their commute or their workday. Is it different for you? Hollywood often depicts a dramatic portrayal of how couples meet, but it doesn't reflect reality for many.

So my advice is relax about trying to "approach" unknown women. You can get better at it but you'll probably get results that make you much happier if you instead focus on expanding your social circle or online dating.
posted by grouse at 8:50 AM on September 8, 2016 [4 favorites]

Pretty much nthing that the beginning of the conversation should be about something of mutual interest. I'm way past the dating stage, but in most any awkward social situation, I'm thinking about asking a question, hopefully in a way that adds some content to the discussion while respecting the other person's opinion. "I thought the plot was formulaic. Do you think that sort of thing can be saved by great acting?"
posted by SemiSalt at 8:52 AM on September 8, 2016

I am a lady that very much likes flirting. But the thing about flirting - it really has to be lit from within, not from without. Guys who cold-flirted with me are legion! Guys I flirted back with all seemed to have a deep enjoyment of women, not for what they could get, but just an enjoyment that women existed in the world. They all projected that they felt genuinely lucky just to talk and banter with a lady. They flirted with the woman where the situation arose, they didn't make a beeline for the prettiest lady and angle for a way to flirt with her. They didn't seem like they were trying to achieve anything - it was non-threatening fun.
posted by corb at 9:33 AM on September 8, 2016 [10 favorites]

I like flirting. It's fun. It's especially fun when the guy knows how to flirt back without seeming like he has an end-game of asking me out and hopefully getting laid. However, I don't think I've ever been approached by a guy who had the specific intention of asking me out that made me feel good.

I don't know why cold approaches are so popular to teach. It's probably the single least successful method of getting a date that exists. It's like saying you have a great money making strategy you'll teach people, but you just tell them to buy ten lottery tickets every day.

Cold approaches require a certain amount of personal confidence, charm, wit, ease with social interaction, and natural instinct for reading people's body language and subtext. You also need a deep understanding that most women you meet are neither available nor looking, so you have to be ok with hearing 'no' a lot. If this doesn't describe you, no formula or tactic is going to change that.

Unfortunately, those characteristics are also shared by boundary-pushing assholes, so even if you possess a full measure of all of them, you're still going to get rejected more often than not. Guys who do "successful" cold approaches just don't let those situations stop them from trying again with someone else until it works. The issue is that if you aren't careful, you will end up turning into a boundary-pushing asshole.

This is probably why personal ads (and now online dating) have existed since the dawn of time. It gives you access to people who have things in common with you, the biggest thing being that they are available and looking.
posted by ananci at 9:59 AM on September 8, 2016 [4 favorites]

There is NO WAY EVER you could approach me that would be ok with me. NO WAY EVER, NONE. It's not a matter of how to approach women you don't know, because you should NEVER do that. You want to date, use online dating or shared activities. LEAVE WOMEN YOU DON'T KNOW ALONE.
posted by Violet Hour at 9:59 AM on September 8, 2016 [5 favorites]

Seconding everyone who says there's almost no way to flirt with women you don't know without coming off as at least slightly creepy. When you do that, you're telegraphing the message that you see her as a sexual object, not a person.

My best recommendation to you: Be friendly. Try and get to know her as a person, without any secondary motives. Once you've established that you have at least a few things in common, and are not an axe murderer in disguise, then maybe try being a little flirty. If it doesn't work, do NOT push. Be happy that you have a female friend, and move on. There is no such thing as the 'friend zone,' there are only assholes who think women owe them sex in exchange for being treated well.

I'm told I flirt a lot, but a) it's based off our pre-existing connection, and mostly unconscious and b) I would never, ever do so if I didn't already know the people I flirt with and trust them not to be axe murderers.
posted by Tamanna at 10:15 AM on September 8, 2016 [1 favorite]

You talk about flirting like it's some act you perform at women. If you're attempting to flirt, you've already failed. Flirting is something that happens when two humans are having both a genuine interaction and happen to be attracted to each other.

So the answer is: Don't do it at all. Just be a person.
posted by cmoj at 10:16 AM on September 8, 2016 [20 favorites]

Before I launch into my strong opinions, I will suggest the movie "The truth about cats and dogs." Also, movies with Kevin Costner. He sets a good example for a man in quite a lot of his roles.

Good flirting with a stranger is totally different from asking for a stranger's phone number. I used to be real flirty, but as so many have already said, so many men are just gross. So I do less of that than I used to.

But a recent incident of positive flirting occured. I was ordering a mocha frappucino no whip (meaning no whip cream on top) at a Starbuck's. The cashier and I had trouble understanding each other and it got repeated a bit by each of us. The guy behind me then repeated it, in fun. So I ended up saying at some point (it made sensecat the time, but I don't recall all the details) "He can have my whip" and I think he or the cashier rebutted that as something like he doesn't need the calories. I shot back "But he apparently needs to be whipped." He sort of restrainedly repeated an old song line: "Whip it good." He clearly knew that was potentially offensive and was careful in how he said it to convey he was playing in a lighthearted way, as was I.

I finished paying and went and sat down. He was obviously a regular and very social. He kept talking with the cashier. He did not bother me. If I see him a jillion more times, maybe months down the line, this might lead to conversation. But I was willing to take a chance on goofing off verbally with him because I felt he was just real sociable, as I am, and this would not become a problem the way such playfulness typically becomes with "desperate for a date" types.

Flirting to enjoy verbal banter and to enjoy a brief social connection with a member of the opposite sex can be okay, but many men get it very wrong. You need to have really good boundaries and not interpret that as an opening to basically jump straight to "So, you are easy and I can get into your panties."

No, I am absolutely not easy. I am quite hard to get next to.

Flirting with strangers needs to combine a genuine enjoyment of their momentary presence in your life with sincere respect. It is ugly if it is merely some means to an end. In other words, if you have just met a woman and would like her phone number based solely on how she looks, that is gross, predatory behavior. Trying to flirt at that point amounts to trying to prey upon her. She is a human being with a complex life. She has hopes and dreams, health issues, social connections and many other things going on.

Reducing her to a person who posseses a pussy you might like to get into, which is something many men do, is just not ever the start of a beautiful relationship. It might be the start of all kinds of drama as you learn this pussy is also a mom, a wife, has blood relatives who might be grudging at your assumption, maybe she is the daughter of your boss or something. She doesn't exist in isolation and you need to be aware of that before you open your mouth and say something flirty. Flirting with a total stranger is risky because you know nothing of the context of their life. You have no idea what you are stepping into.

If you want to learn to flirt in a way that can lead to sex, as so many have already said, this takes place in the context of an established relationship. You are already friends. You already treat her like a human being and not just a piece of meat that might service you sexually at some point.

A man I knew for a couple of weeks and had talked with for many hours in that short time told me he did not get involved with women my age. They were too young. I replied that I guess we will need to wait a year so I can get old enough. He said an exception could be made for an exceptional woman. We did not wait a year. He was an important part of my life for the next few years.

He came from a culture which was very much Guess Culture, something I was not aware of at the time. Looking back on it, that was probably his way of floating the idea of us getting together in a manner that erred on the side of making it easy for me to say "no." He started with No and gave me the option to rebutt that, if I was interested. I was interested. So I rebutted it in a way that respected his stated boundary. I indicated I would wait until I was old enough in his eyes.

Guess Culture is about having a pretty good idea of what the answer will be before you delicately broach the topic. It requires you to have a good deal of context to read the situation. You cannot communicate that way with someone you just met. There simply isn't enough information available to infer the answer before you delicately probe in a way that sincerely respects their right to decline.

Flirtation should never be about manipulating a woman's feelings. It is okay if it shows your hand and is a mild confession of interest. There should be zero pressure to reciprocate.

It is about being fun and playful and enjoying people. If that enjoyment is at their expense, it is asshole Pick Up Artist crap, not flirting.

I am not accusing you of anything. I am just trying to clearly delineate the difference. I wish there was more good flirting in my world. So I certainly hope you succeed in figuring this out.

posted by Michele in California at 10:34 AM on September 8, 2016 [2 favorites]

I think the best way to think about this is to practice flirting as a separate skill from actually trying to cultivate a relationship with a particular person that will lead to a date/romance. You can flirt with someone of either gender, whether or not you are actually attracted to them. You can flirt with babies and old men and your family members.

It's just a form of being extra friendly and nice that is directed at a single person in a way that feels "special." Just think of it as really making someone feel good, and giving them some special attention. A key part of it for me is that it feels sweetly between just the two of you, even if a group is around.

Really the easiest way is to make intentional eye contact, hold it, and give a real, genuine, smile! Grin at them. Keep holding that eye contact, or look down shyly while still smiling. There! You just flirted.

Can you do something small that is sweet and thoughtful just for them? Grab them a napkin or fork if you are at a coffee shop or about to eat, offer to refill their drink at a party? That's flirting.

Teasing, touch, compliments, jokes - these are honestly Flirting 201 and you should just get comfortable with Flirting 101 - hold eye contact, smile, be *extra-nice*, just to them - first.
posted by amaire at 10:37 AM on September 8, 2016 [2 favorites]

One thing that can be helpful is getting better at small talk. When folks above talk about how important it is that a stranger talking to them didn't seem to have an agenda, that's the beauty of good small talk. And that you can start doing that with Everyone. On the elevator, in the check out line, wherever you're likely to be interacting with strangers and it's awkward to be silent, try a little small talk: weather, a compliment on something safe, shared experience, pets. Because the beauty of small talk is it's low stakes and often builds connections. Which isn't the same thing as flirting, but is related, and a little human connection in the day can make all lives a little happier.
posted by ldthomps at 10:39 AM on September 8, 2016 [3 favorites]

I will add that the guy at the Starbuck's was clearly counting on his pre-existing relationship with the cashier to help make sure things did not go sideways. This was not really "cold calling" because she was serving as his wingman. Had I gotten in a snit, she wouod likely have smoothed things over. He was interacting with both of us verbally and he could count on her to not be offended because they already had a positive social connection.
posted by Michele in California at 10:43 AM on September 8, 2016


As long as you're not engaging in problematic behaviors (hitting on service industry workers, hitting on women in confined spaces where they can't say no and get away, not taking no for an answer, getting hostile, etc), pretty much anything goes. There's no script for this stuff. Just don't be a blatant asshole and you're fine.

The only real point of advice I have is that not being a blatant asshole, in a lot of ways, is about remembering that flirting is a conversation. Listen as much as you talk. Take in her body language and whether she is responding back in kind or rejecting you. Only make your next move based on the last move.

Things that have not gone over well with me:

- People getting up in my space
- People not backing off when it's clear I'm not interested
- People who think that flirting is a sales pitch, that the goal is to get me to do something I may not want to do
- Flirting as the first point of contact from a complete stranger

Things that have gone over well with me:

- Flirting in a social situation where we're already talking or otherwise having some kind of shared social behavior.
- Being perceptive of whether I appear interested or not.
- Understanding that you're looking for a person who is into you, not a person you can force to pretend that she's into you.
- Flirting with me when we already know each other and aren't complete strangers.
posted by Sara C. at 11:46 AM on September 8, 2016

Response by poster: My original thinking with this question was grounded in the TV sitcom narrative of "boy meets girl at the bar, they flirt a bit, [something happens off camera], they wake up in bed together the next morning."

But, of course, reading these responses, that narrative makes no sense. It's a common story with no grounding in reality. Even the most attractive stranger is still a dangerous unknown. I'm sure the TV narrative happens, but it's not the way most actual relationships work.

The consensus I'm seeing is basically: Flirting is not a good opening move. Make friends first. Get to know people without any expectations.

Where I'm getting tripped up is in how to indicate romantic interest in people who I have established a connection with. Like, I know how to make friends, and I can ask someone I'm friends with on a date. What I don't know is where to go from there.

My religious background basically tells me "don't touch people you aren't married to, at all, outside of handshakes/greetings or hugging them in times of grief." The feminist culture here makes it clear that women get way more attention than they want from men.

So my default reaction is to avoid all physical contact, which is as good as saying "I'm not really that into you." I don't know how to go beyond friendly conversation into something physical. I think that's what I'm looking for positive examples of.

I apologize if any of this feels like you're explaining the basics of human interaction. I have to admit feeling pretty embarrassed by my ignorance.
posted by JDHarper at 12:19 PM on September 8, 2016 [6 favorites]

I think the key is to practice flirting in environments where flirting is going to be welcome. If you meet someone through online dating, they are not going to be totally shocked if you flirt with them. Or late night at the local bar where singles meet.
posted by grouse at 12:31 PM on September 8, 2016

Mod note: One comment deleted. Folks please focus on concrete suggestions about what a welcome respectful version of this looks like, rather than repeating what the negatives are.
posted by LobsterMitten (staff) at 12:43 PM on September 8, 2016

I am a relatively nervous sort when it comes to being approached by strangers. What has worked for me:

1. I am in an environment where I feel relatively comfortable (if you can gauge this easily)
2. We already have something in common (participating in a shared hobby or interest)
3. The person greets me, introduces themselves, and either makes a light joke about the something in common ("I had to step away from the games table for a few minutes - those Settlers of Catan players are serious business!" or "That 7th steak taco might have been my undoing!" for example) or asks a question about the something in common ("Bride's side or groom's side?" or "Are you familiar with this band?" for example) to start a conversation

If the conversation flows relatively naturally and there are laughs and smiles, invite the person to something very low stakes ("Hey, I'm grabbing a drink at the bar, can I get you something?" or "Would you like to join our table?" or "Any interest in dancing?") - if she says no, move on to doing your own thing. If she is interested, in my experience, she will recognize that you weren't simply offering a drink/dance/whatever but were extending an invitation, and will seek you out for more chatting. If she says yes, enjoy the drink/dance/whatever, chat a bit more, and invite her to do something specific with you on a specific date and phrase it as a date ("Have you tried the new tapas place in Brixton? Would you be interested in joining me for dinner there next Friday, as a date?") - if she says no and offers no alternative activity or date ("I'm allergic to tapas, how about fish & chips?" or "I can't Friday, but how about Thursday?") then she is likely not interested. But you've gone about things in a way that even frightened-bunny/mildly-clueless me would both feel comfortable with and understand as a flirt/date-asking situation.

As for how to get from date to more-than-date, as someone who doesn't always get hints but can get jumpy around unexpected physical contact, I have a soft spot for the frank, "Can I hold your hand?" when on a walk or "Can I kiss you?" at the end of the date (rather than mid-date, in case she demurs, which is a little awkward if you ask when it seems like a romantic moment but she's not with you on the romantic thing). As a woman, I feel comfortable escalating from there ("Would you like to come up?" etc). The right woman will find your lack of suave-itude charming.
posted by pammeke at 12:46 PM on September 8, 2016 [2 favorites]

Where I'm getting tripped up is in how to indicate romantic interest in people who I have established a connection with. Like, I know how to make friends, and I can ask someone I'm friends with on a date. What I don't know is where to go from there.

I hope I'm not coming across as derisive or anything like that by making this seem obvious or easy (believe me I know it's not), but I've had general success in the past in this department with, "So, uh, I'm really attracted to you. Like, you're cool and stuff."

The thing about that is, if that feeling is reciprocated at all, it makes no difference whatsoever if you're (as I have been) all awkward about it. Just say a true thing about what you feel.
posted by cmoj at 1:00 PM on September 8, 2016 [1 favorite]

Make them laugh and expect nothing in return
posted by Kwadeng at 2:44 PM on September 8, 2016

Where I'm getting tripped up is in how to indicate romantic interest in people who I have established a connection with. Like, I know how to make friends, and I can ask someone I'm friends with on a date. What I don't know is where to go from there.

If you and your friend have fun on the first date, ask her on a second. If you're both having fun on the second date, ask her on a third. If you guys aren't naturally getting physically closer during those dates, like sitting next to each other and bumping shoulders, or her touching your arm when she says something, then it's totally ok to use your words to say, "I'm really having a good time with you and I'm a little nervous about asking this, but would it be ok if I kissed you goodnight?" It's going to seem a little awkward, sure, but if it's asked of someone who is already enjoying your company, and not someone you've just met, it will be charmingly awkward, not bad awkward. I'm a big dork who has dated a lot of other big dorks and none of us are smooth with the moves, and yet we still manage. The only time a guy asking if he could kiss me ever got weird was when a guy asked if he could kiss my neck as a first kiss. Like right behind my ear. Which is a sexy move if you're already making out, but is hella awkward on a random street corner outside a restaurant.
posted by MsMolly at 3:01 PM on September 8, 2016 [6 favorites]

Regarding the original question, I have twice actually agreed to a date with a man I had just met that evening. On both occasions, we had met at a smallish house party, had a good time talking together for several hours, and on one of them the mutual friend who invited us both pulled me aside at some point and explicitly vouched for him. In the other case, most of the talking also involved a mutual friend; said friend made it pretty clear he thought this was a good idea. I'm sure some of the talking got flirtatious but the only reason it went farther than talk was because someone I trusted vouched for them. (In one case we dated for a few months, in the other it turned out it was the whiskey that was fun, not him so much).

As for flirting with women you already know, and have already indicated explicit interest in (by asking her out on a date, as a date), that is going to depend on the relationship between you. For me, doing some actual activity together provides more flirting opportunities- if it's something physical you can help each other out, joke about awkwardness, touch briefly for necessary reasons (which allows for extension if you both want it). Board/video games provide plenty of banter opportunity; movies/music/plays give a shared piece to discuss and place in the context of broader likes/dislikes.

As far as the religious upbringing, I can't speak to that specifically, but perhaps you will find the concept of enthusiastic consent to be useful. It probably isn't possible to ask if she's enjoying every minute of the date, but if these women are friends you ought to be able to tell. Enjoy being around someone who is enjoying being around you.

And asking for permission before physical touch can totally be done in a sexy manner. Getting a positive reply is not only pretty great itself but might help you satisfy your wish to do right by the women in your life. (Perhaps replace "no touch before marriage" with "It is ok to touch someone if and how that someone says explicitly that they want to be touched!")
posted by nat at 3:36 PM on September 8, 2016 [1 favorite]

A lot of more-than-friendly interest can be conveyed by an escalating conversation involving eyes only. Holding gaze a beat longer than usual, looking at them when laughing, etc. This is bi-directional- if she's going along with this, if she's not immediately snapping her eyes away but is lingering as well, that's a reasonably good sign.

(if she really blatantly rolls her eyes as she looks away from you, oh my God just drop it please. She's not interested. Do not pursue.)

The first step isn't touch, it's proximity. People have circles of personal space, and there's a level of physical proximity that is closer than the one we maintain naturally between not-super-close friends. Drift carefully into that space and see the reaction.

Generally: the sign you're looking for is a matching move from her. You shift a little closer to her, and she matches this by shifting a little closer to you (it's a body language mirroring she wouldn't necessarily be consciously aware of). If she instead readjusts away to maintain the previous distance, do not re-close the distance, let it go.

Start with touch to safe zones of the body. A light touch to the hand is fairly safe, whereas arms, shoulders are an escalation thereof. Upper back. You can also match her - if she let your legs come into contact with hers, you don't need to flinch away. Just don't push.

Back off immediately if, for example, she flinches, freezes, or her body language shifts towards "escape routes" - eyes darting to sides, body angling away. Also not a good thing: openly fiddles with phone, clutches bag close to body, or openly seeking a distraction, bringing another person into conversation, etc.

And when I say back off I mean actually physically move back so there's a safe amount of space between you.


But at some point the simplest thing is to just use words. To say, "I think you're cool, I'd like to spend time with you, would you be interested in meeting up xyz". If she demurs because of scheduling conflict it could be a soft no or an actual scheduling conflict, so I'd just say "alright, well let me know if there's another time that works better" and let it drop completely.
posted by Cozybee at 9:09 PM on September 8, 2016 [1 favorite]

Where I'm getting tripped up is in how to indicate romantic interest in people who I have established a connection with. Like, I know how to make friends, and I can ask someone I'm friends with on a date. What I don't know is where to go from there.

Thanks for clarifying! I think of "flirting" as something entirely different (fun, casual, not necessarily an expression of actual romantic interest).

I think this advice from Paul J. Wilczynski is pretty good. Excerpt:
1. With rare exceptions, women are not offended if you make a pass at them, as long as it's done with some amount of taste. In fact, after a fairly short period of time (mileage may vary), women draw an important conclusion if you don't make a pass. And that conclusion is that you're not terribly interested in being more than a friend. Let me explain that I consider 'make a pass' to be a very broad term ... it can be something as non-threatening as putting your hand on her arm briefly and telling her that you think she looks especially nice tonight.
In short, something that indicates you're interested--you're making the first move--but that's subtle enough that if she's not interested, you won't be terribly embarrassed. A kiss on the cheek at the end of the evening is another possibility.
posted by russilwvong at 9:55 PM on September 8, 2016 [1 favorite]

Flirting is only effective when it is (i) respectful; (ii) open-ended, so if I sense that a guy is hitting on me with the expectation of me acting a certain way in return... I shuffle away ASAP.

I think you should watch some romantic comedies! Those things are highly popular with the ladies and performed by some super charming actors who are literally pro at flirting. And it might be more helpful to watch demos than read written manuals for a practical skill like this.

Here are some lists! Or you could watch some clips on youtube I guess, if you don't enjoy watching through romantic comedies:
Rotten Tomatoes guide to Romantic Comedies
Top 100 Grossing Romantic Comedy films.

Maybe figure out what style of flirting you prefer, and then go out and practise? You can do it! Good luck!
posted by Crookshanks_Meow at 12:16 PM on September 9, 2016

2nding every thing Cozybee said.

Also, it sounds like you might benefit from some exposure to non-sexual touching with members of the opposite sex in a scenario where there is no expectation of taking things further. Partner dancing is excellent for this kind of thing. You'll be able to get used to both proximity and touching in ways that are safe and consensual, so that when you are in front of someone you like you have some skills to call upon.

An added bonus is that partner dancing can really enhance those 'mirroring' skills that are so important when shifting from proximity to touching. It will improve your ability to pick up small non-verbal cues that will help with making both you and your date more comfortable with the pacing and direction of what's happening.
posted by ananci at 10:43 AM on September 10, 2016

Flirting between strangers happens when both parties silently acknowledge a spontaneous and / or serendipitous connection. That connection can be physical, intellectual, circumstantial or any other -al. You can increase the probability of this happening. How? Be genuine and friendly towards everybody without expecting anything in return. When you do that, the people you are meant to mutually flirt with will appear.
posted by jasondigitized at 1:28 PM on September 10, 2016 [1 favorite]

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