A (hopefully fun) question about flirting
September 20, 2023 6:01 AM Subscribe
Many days on my way to work I walk pastthe same attractive man around my age who always smiles and says hello. How do I try to get to know him a little?
On my walk to work in a large US city I am usually tuning out the world with my headphones in. I started noticing a certain man that would smile as we walked passed each other. He's my age (mid-40s) and has a similar "vibe" (social worker type).
I am a shy person but I would love to at least attempt some sort of conversation. Looking for ideas about how to do this what to say, etc. I do always smile at him.
Also, this happens sometimes with other people on the street that I find attractive (they smile at me). I'd loveto meet more people, potentially to date.
Ideas from flirtatious extroverts, or introverts who have also learned this skill (or anyone who has some ideas/experience) welcome!
Would also love some stories/examples about meet-cutes and how they happened
On my walk to work in a large US city I am usually tuning out the world with my headphones in. I started noticing a certain man that would smile as we walked passed each other. He's my age (mid-40s) and has a similar "vibe" (social worker type).
I am a shy person but I would love to at least attempt some sort of conversation. Looking for ideas about how to do this what to say, etc. I do always smile at him.
Also, this happens sometimes with other people on the street that I find attractive (they smile at me). I'd loveto meet more people, potentially to date.
Ideas from flirtatious extroverts, or introverts who have also learned this skill (or anyone who has some ideas/experience) welcome!
Would also love some stories/examples about meet-cutes and how they happened
I would not call myself a flirtatious extrovert but I have successfully gotten to know (or at least talk to) people I routinely pass on the street! I just stopped and said, "I see you almost every day - I feel like I should introduce myself! I'm Kyle." And from then on we had a relationship where instead of just saying hello in passing, we would sometimes stop and have a chat. In my case this never escalated to an actual outside-of-seeing-each-other-on-the-street friendship/relationship, but it was still nice. Weak tie relationships are great!
posted by mskyle at 6:23 AM on September 20, 2023 [24 favorites]
posted by mskyle at 6:23 AM on September 20, 2023 [24 favorites]
This is adorable!
Introvert non-flirt, chiming in here...one strategy might be to wear your headphones and then, when you see him coming, take them out, while smiling with eye contact, and maybe slow down your walk a little. If he's perceptive, hopefully he'll notice that and do the same. From there, it's just a matter "hi!" and then see what happens.
Maybe a joke or light-hearted comment about how no one remembers how to interact with strangers/meet new people. For me, pointing directly at potential awkwardness helps to ease the awkwardness.
Good luck! Let us know how it goes!
posted by gold bridges at 6:23 AM on September 20, 2023 [6 favorites]
Introvert non-flirt, chiming in here...one strategy might be to wear your headphones and then, when you see him coming, take them out, while smiling with eye contact, and maybe slow down your walk a little. If he's perceptive, hopefully he'll notice that and do the same. From there, it's just a matter "hi!" and then see what happens.
Maybe a joke or light-hearted comment about how no one remembers how to interact with strangers/meet new people. For me, pointing directly at potential awkwardness helps to ease the awkwardness.
Good luck! Let us know how it goes!
posted by gold bridges at 6:23 AM on September 20, 2023 [6 favorites]
If all you have done so far is smile and say hello, maybe just add a few words like, "How are you today?" and stop for a second, keeping your body language very open? It sounds like the work is pretty much done for you here.
posted by BibiRose at 6:23 AM on September 20, 2023 [1 favorite]
posted by BibiRose at 6:23 AM on September 20, 2023 [1 favorite]
Since he always says hello, you could just start replying, in addition to the smile.
posted by tomboko at 6:25 AM on September 20, 2023 [1 favorite]
posted by tomboko at 6:25 AM on September 20, 2023 [1 favorite]
I'm a big fan of breaking the ice in that situation. I like the scripts above; I'd probably use a variation of this one: "I see you almost every day - I feel like I should introduce myself! I'm Kyle.""
Once you have broken the ice somehow, then it is more a question of reading the room and assessing if the person is open to either gradually more contact (like chatting a bit more each week) or maybe open to an actual date-type invitation, or if they maybe seem pleasant but not very interested in contact, or you can figure out quickly that they aren't single.
Since you asked for examples, I met my spouse this way. I'd seen her around but we had never spoken, and then we both ended up at an event. I saw her sitting alone so I just walked over and introduced myself, which led to chatting, which led to exchanging contacts, which led to a date.
posted by Dip Flash at 6:50 AM on September 20, 2023 [3 favorites]
Once you have broken the ice somehow, then it is more a question of reading the room and assessing if the person is open to either gradually more contact (like chatting a bit more each week) or maybe open to an actual date-type invitation, or if they maybe seem pleasant but not very interested in contact, or you can figure out quickly that they aren't single.
Since you asked for examples, I met my spouse this way. I'd seen her around but we had never spoken, and then we both ended up at an event. I saw her sitting alone so I just walked over and introduced myself, which led to chatting, which led to exchanging contacts, which led to a date.
posted by Dip Flash at 6:50 AM on September 20, 2023 [3 favorites]
Response by poster: I do say hello!
posted by bearette at 6:56 AM on September 20, 2023 [3 favorites]
posted by bearette at 6:56 AM on September 20, 2023 [3 favorites]
I find the transition to a conversation is so much easier and more natural when there’s something you can comment on—the weather is good! A guy is weird! A dog is there! Really anything. I would never be able to say “I thought I should introduce myself” without a conversation first but I’ve had tons of luck creating a conversation out of One Weird Thing You Both Saw. You could try to manufacture such a situation by carrying, say, a prominently-displayed book or a tote bag with something written on it.
posted by babelfish at 7:02 AM on September 20, 2023 [13 favorites]
posted by babelfish at 7:02 AM on September 20, 2023 [13 favorites]
Seconding escalating “hello!” to “how’s it going?”
For a couple weeks the answer will probably just be filler. “Good, thanks!” Delivery, eyes and tone will tell you more than actual words. Chill at this level for a bit.
But it’s autumn! People start wearing different clothes in autumn. “Oh hey, new hat/scarf/coat? I like the color!”
Just random little things. Let conversation build till you get to the “so, doing anything fun this weekend?” stage.
Be prepared for him to be married, or not attracted to your gender, or otherwise unavailable. Sometimes a no-strings hello in the street with some wistful what-ifs attached is all that’s possible. And that too is perfect in its way.
posted by Pallas Athena at 7:08 AM on September 20, 2023 [15 favorites]
For a couple weeks the answer will probably just be filler. “Good, thanks!” Delivery, eyes and tone will tell you more than actual words. Chill at this level for a bit.
But it’s autumn! People start wearing different clothes in autumn. “Oh hey, new hat/scarf/coat? I like the color!”
Just random little things. Let conversation build till you get to the “so, doing anything fun this weekend?” stage.
Be prepared for him to be married, or not attracted to your gender, or otherwise unavailable. Sometimes a no-strings hello in the street with some wistful what-ifs attached is all that’s possible. And that too is perfect in its way.
posted by Pallas Athena at 7:08 AM on September 20, 2023 [15 favorites]
As an introvert who’s learned the skill somewhat, the key is to say anything. Looking for the right thing to say is overthinking it. You can say any damn idiot thing you want - just greet him and make an observation on something in your environment. The key here is to ignore the words and focus on the type of energy you want to transmit in the interaction. Talk about whatever you want but keep your focus on how attractive he is and what you want to do with him, and it’ll evolve from there.
posted by wheatlets at 7:23 AM on September 20, 2023 [11 favorites]
posted by wheatlets at 7:23 AM on September 20, 2023 [11 favorites]
Fake drop something, and see if he stops to help to pick it up, or at least comments on it. Automatically gives you a deeper conversation than 'hello' if you are really shy and you can have some fun practicing and finding something to drop.
posted by The_Vegetables at 7:27 AM on September 20, 2023 [2 favorites]
posted by The_Vegetables at 7:27 AM on September 20, 2023 [2 favorites]
I love this question! Just wanted to say that this was one of my favorite things about commuting to work by foot/public transportation. You see the same people over and over and there's a certain familiarity that builds between people, even if you might think it's just on your side.
I remember when I used to see this guy on the same train platform as me because of the timing of our train transfers. We only said hello a few times over the course of 3 years but that was it. Once I switched jobs, my schedule changed and so did my commute times. However one day about a year later, for some reason, I had to take the same trains from my old route, and he was there on the platform! He came over and swatted at me with his newspaper and said, "Long time no see!" I was shocked that he remembered me. We chatted for a bit before my train came.
I switched jobs again and moved, and now I drive to work. It's fine, but I miss having commuter buddies.
posted by extramundane at 7:31 AM on September 20, 2023 [3 favorites]
I remember when I used to see this guy on the same train platform as me because of the timing of our train transfers. We only said hello a few times over the course of 3 years but that was it. Once I switched jobs, my schedule changed and so did my commute times. However one day about a year later, for some reason, I had to take the same trains from my old route, and he was there on the platform! He came over and swatted at me with his newspaper and said, "Long time no see!" I was shocked that he remembered me. We chatted for a bit before my train came.
I switched jobs again and moved, and now I drive to work. It's fine, but I miss having commuter buddies.
posted by extramundane at 7:31 AM on September 20, 2023 [3 favorites]
Fellow sometimes-shy person here, with one tiny note to remember about this.
I absolutely think you should do this, but I would also bear in mind that maybe he's not specifically saying hi just to you, you know? Maybe he is just being friendly. The actor Jesse L. Martin and I were in the same acting studio in college (he was a year ahead of me) and he would do exactly this same thing to me, because he was so used to recognizing me around campus. We never were formally introduced, we just started recognizing each other from passing each other in the hallway so much, and he'd always give me a big smile and a "Hey, how ya doin'?"
That said - that's ironically maybe exactly what you need to be doing too. Just little random small-talk things ("gorgeous day, isn't it?") or a slight joke about how often you see each other ("we see each other so much you probably should at least know my name!") or something. Or if not, you can just keep saying "Hi" and that's it. I mean, Jesse and I never moved beyond that, and I still appreciate it nearly 30 years later.
posted by EmpressCallipygos at 7:33 AM on September 20, 2023 [2 favorites]
I absolutely think you should do this, but I would also bear in mind that maybe he's not specifically saying hi just to you, you know? Maybe he is just being friendly. The actor Jesse L. Martin and I were in the same acting studio in college (he was a year ahead of me) and he would do exactly this same thing to me, because he was so used to recognizing me around campus. We never were formally introduced, we just started recognizing each other from passing each other in the hallway so much, and he'd always give me a big smile and a "Hey, how ya doin'?"
That said - that's ironically maybe exactly what you need to be doing too. Just little random small-talk things ("gorgeous day, isn't it?") or a slight joke about how often you see each other ("we see each other so much you probably should at least know my name!") or something. Or if not, you can just keep saying "Hi" and that's it. I mean, Jesse and I never moved beyond that, and I still appreciate it nearly 30 years later.
posted by EmpressCallipygos at 7:33 AM on September 20, 2023 [2 favorites]
Fake drop something, and see if he stops to help to pick it up, or at least comments on it. Automatically gives you a deeper conversation than 'hello' if you are really shy and you can have some fun practicing and finding something to drop.
Came in here to say this! This is the classic thing!
It also gives you conversational fodder on subsequent days ("Hey, I just wanted to thank you for helping me pick up all those kazoos the other day!"), which will give you a sense of whether he's receptive to further interaction or not.
posted by Blue Jello Elf at 8:10 AM on September 20, 2023
Came in here to say this! This is the classic thing!
It also gives you conversational fodder on subsequent days ("Hey, I just wanted to thank you for helping me pick up all those kazoos the other day!"), which will give you a sense of whether he's receptive to further interaction or not.
posted by Blue Jello Elf at 8:10 AM on September 20, 2023
I would lean towards something like "Hey, the roses are blooming in the garden in the direction you're headed; make sure you check them out!" rather than "Let me introduce myself" because it more easily leads to future interactions. (Such as the next day him saying "Thanks for pointing out the roses to me! Did you see the dahlias on Willett Street?" As an introvert, I would also prefer receiving that rather than a formal introduction, because it does not demand as much effort to respond.
posted by metasarah at 8:34 AM on September 20, 2023 [6 favorites]
posted by metasarah at 8:34 AM on September 20, 2023 [6 favorites]
Non-flirty in my case, but I’ve had a lot of luck turning strangers into a first-name basis with a smile and “we’ve got to stop meeting like this.”
posted by Mchelly at 8:37 AM on September 20, 2023
posted by Mchelly at 8:37 AM on September 20, 2023
If it's only on the way in, this doesn't work, but if you see him on the way home, get a couple gift cards to a coffee shop or bar nearby. Tell him your friend had a lot extra for some reason and you are sharing them. Would he like to join you?
Basically any white lie excuse might make it easier for you to ask him for a light coffee date or make it easier for him to accept.
posted by SaltySalticid at 8:48 AM on September 20, 2023 [1 favorite]
Basically any white lie excuse might make it easier for you to ask him for a light coffee date or make it easier for him to accept.
posted by SaltySalticid at 8:48 AM on September 20, 2023 [1 favorite]
Plenty of solid suggestions here, but if you wanted to kick it up a notch, maybe try something unusual on your way to work that makes it so he just has to ask: carry a giant teddy bear bigger than you, be walking 20 small dogs, be dressed normally, but completely soaking wet. Then have a story ready when he asks!
posted by snofoam at 9:24 AM on September 20, 2023
posted by snofoam at 9:24 AM on September 20, 2023
I'm not extroverted or easily flirty, and I'd personally find being on the receiving end of "how are you?" to be daunting - like yeah, you're escalating things a bit, but in a way that dumps the work on the other person.
With the caveat that I'm a bit weird, I'd escalate things a lot more by revealing that you've noticed something about him, because people generally are flattered by that:
has a similar "vibe" (social worker type).
So I'd go with "Hey, if you don't mind I'm wondering if I can test out my intuition on you - any chance you're a social worker?"
If he is, cool, you have something to talk about. If he's not, well, you're going to learn what he does do for work, and then you can talk about that - maybe this will be a dead end, but I'd say it has more of a shot than "how are you?"
posted by coffeecat at 9:28 AM on September 20, 2023 [6 favorites]
With the caveat that I'm a bit weird, I'd escalate things a lot more by revealing that you've noticed something about him, because people generally are flattered by that:
has a similar "vibe" (social worker type).
So I'd go with "Hey, if you don't mind I'm wondering if I can test out my intuition on you - any chance you're a social worker?"
If he is, cool, you have something to talk about. If he's not, well, you're going to learn what he does do for work, and then you can talk about that - maybe this will be a dead end, but I'd say it has more of a shot than "how are you?"
posted by coffeecat at 9:28 AM on September 20, 2023 [6 favorites]
Figure out some very local event - a fundraiser for the foodbank, a book signing, last day of the farmer's market, then make up a pretty flyer, not too special, not fancy, xerox a bunch. On your next walk hand them out to everyone you see. "Hi, I'm volunteering at the foodbank fundraiser (note: actually volunteer if this is your option, be honest of course) hope you can attend! There will be music and snacks!" or "my favorite author has a book signing on Saturday, I'm trying to raise interest for her, hope you can stop by!"
Be very non chalant, you are not desperate.
1. by giving a flyer to everyone he will see you are not targeting him, takes the pressure off
2. if he is interested in you he will show up
3. I have suggested small events so he can spot you
4. I wouldn't give up on this if he doesn't come to the first invitation, I would try at least twice
posted by cda at 9:30 AM on September 20, 2023
Be very non chalant, you are not desperate.
1. by giving a flyer to everyone he will see you are not targeting him, takes the pressure off
2. if he is interested in you he will show up
3. I have suggested small events so he can spot you
4. I wouldn't give up on this if he doesn't come to the first invitation, I would try at least twice
posted by cda at 9:30 AM on September 20, 2023
Big smile, slow down, gesture to yourself and tell him your name. Be ready to stop and chat.
But just the name with the gesture, at first. Don't pad it out with nervous chatter.
posted by fingersandtoes at 9:41 AM on September 20, 2023 [1 favorite]
But just the name with the gesture, at first. Don't pad it out with nervous chatter.
posted by fingersandtoes at 9:41 AM on September 20, 2023 [1 favorite]
1. by giving a flyer to everyone he will see you are not targeting him, takes the pressure off
God no. Remember your Mitch Hedburg: Handing me a flyer is saying 'here, you throw this away'. They try this in Las Vegas with hot people, scantily dressed people, interestingly dressed people - it doesn't work. The majority of people still dodge like a cannonball is coming their way.
posted by The_Vegetables at 9:52 AM on September 20, 2023 [11 favorites]
God no. Remember your Mitch Hedburg: Handing me a flyer is saying 'here, you throw this away'. They try this in Las Vegas with hot people, scantily dressed people, interestingly dressed people - it doesn't work. The majority of people still dodge like a cannonball is coming their way.
posted by The_Vegetables at 9:52 AM on September 20, 2023 [11 favorites]
Hand him your phone number.
posted by summerstorm at 10:02 AM on September 20, 2023 [2 favorites]
posted by summerstorm at 10:02 AM on September 20, 2023 [2 favorites]
Totally fine and cool to start a chat on your next encounter. But the best way to really break this walking greeting with someone like this, I've found, is if you bump into them elsewhere in the city, or if you can slightly alter your schedule so you see them on a different part of the normal route. Then it's like youre old friends bumping into each other. It's funny how seeing the same person elsewhere creates a natural friendly opening, so often. However I would absolutely not go to any lengths or real effort or anything complicated to manipulate this.
Also: as a woman I actually would not feel safe to give my phone number to a random stranger, nor invite them out for coffee. He is still a random stranger even though he has a nice smile. It's easy to feel like you know someone when you smile at each other in the street but you only know your fantasy of him. Take it slow. You have zero way of knowing his relationship status nor his creepiness status at this point.
posted by rainy day girl at 10:26 AM on September 20, 2023 [1 favorite]
Also: as a woman I actually would not feel safe to give my phone number to a random stranger, nor invite them out for coffee. He is still a random stranger even though he has a nice smile. It's easy to feel like you know someone when you smile at each other in the street but you only know your fantasy of him. Take it slow. You have zero way of knowing his relationship status nor his creepiness status at this point.
posted by rainy day girl at 10:26 AM on September 20, 2023 [1 favorite]
Next time you see him, cheerily say "Good morning!" or "Good afternoon!" first, with a big smile. Raise your eyebrows as you do this.
If he has his headphones in and has to stop to say, "Sorry, what did you say?" then that's your opportunity to introduce yourself.
posted by bluedaisy at 11:25 AM on September 20, 2023 [1 favorite]
If he has his headphones in and has to stop to say, "Sorry, what did you say?" then that's your opportunity to introduce yourself.
posted by bluedaisy at 11:25 AM on September 20, 2023 [1 favorite]
You can also say something like, "I really appreciate you saying hello in the morning. It's a highlight of my walk to work."
posted by bluedaisy at 11:27 AM on September 20, 2023 [2 favorites]
posted by bluedaisy at 11:27 AM on September 20, 2023 [2 favorites]
As an introverted man, a thing that worked with me was when the other person said “Hey, we see each other every day, seems like we introduce ourselves or something., don’t you think?”
posted by rodlymight at 11:45 AM on September 20, 2023
posted by rodlymight at 11:45 AM on September 20, 2023
In psychology, he would be defined as a "familiar stranger": someone who you see regularly in your day-to-day life, you recognize each other, but are not actually acquainted. Apparently, we are more likely to actually talk to the familiar stranger when we encounter them outside of the usual context. See if you can change your route to run into him at a different place, or circle back so that you're walking in the same direction as he does for a bit - it will increase the chances that you will have more of a conversation.
posted by 5_13_23_42_69_666 at 12:26 PM on September 20, 2023 [1 favorite]
posted by 5_13_23_42_69_666 at 12:26 PM on September 20, 2023 [1 favorite]
From watching a friend who could chat up anyone, create a shared situation or comment on a shared situation. The fake drop is but one example. But basically you’re looking for opportunities to take it from you vs me (strangers) to us vs. the situation (which brings us a touch closer). Not sure of your surroundings but using the weather may also be an option. If you pass by a news stand at the same time you can point to a headline and make a joke. I hope that helps stir some ideas.
posted by St. Peepsburg at 4:13 PM on September 20, 2023 [3 favorites]
posted by St. Peepsburg at 4:13 PM on September 20, 2023 [3 favorites]
You already have a shared situation, though! It's your walk to work! That's your in!
I feel like most folks posting on this thread are making this way too complicated.
posted by mskyle at 7:23 AM on September 21, 2023 [3 favorites]
I feel like most folks posting on this thread are making this way too complicated.
posted by mskyle at 7:23 AM on September 21, 2023 [3 favorites]
You already have a shared situation, though! It's your walk to work! That's your in!
For a shy person that's just not much of an 'in' as people can literally pass people for many years and never pass beyond the 'hi' stage. I think Jane Jacobs called this the 'sidewalk ballet', and is too common to be useful, unless you are extroverted. But if you are, then anything is an 'in'. That's why creating a shared situation, involving action, opens up specific things to talk about, lessening anxiety, and will hopefully help guide another person to first take an action, which also reduces anxiety, and possibly conforms to gender roles.
posted by The_Vegetables at 9:41 AM on September 21, 2023
For a shy person that's just not much of an 'in' as people can literally pass people for many years and never pass beyond the 'hi' stage. I think Jane Jacobs called this the 'sidewalk ballet', and is too common to be useful, unless you are extroverted. But if you are, then anything is an 'in'. That's why creating a shared situation, involving action, opens up specific things to talk about, lessening anxiety, and will hopefully help guide another person to first take an action, which also reduces anxiety, and possibly conforms to gender roles.
posted by The_Vegetables at 9:41 AM on September 21, 2023
If your big US city is anything like mine, I have found that bitter complaining bonds us as a people! After "Hello," go, "This subway line sucks, amirite?" Next thing you know you'll both be tawking just fine!
posted by Wylie Kyoto at 9:48 AM on September 21, 2023
posted by Wylie Kyoto at 9:48 AM on September 21, 2023
Is there a coffee shop you both walk by? As you pass him, you could say something like, “At XYZ Cafe back there I had the cheese danish. So good! If you like cheese danishes, you gotta try it.”
It wouldn’t put pressure on him to have a conversation, and it gives him an opening if he wants to have one ever.
posted by pickles_have_souls at 5:23 PM on September 23, 2023
It wouldn’t put pressure on him to have a conversation, and it gives him an opening if he wants to have one ever.
posted by pickles_have_souls at 5:23 PM on September 23, 2023
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posted by rhymedirective at 6:22 AM on September 20, 2023 [25 favorites]