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Even though the number of single adults started to decline for the first time in two decades, a lot of people still talk about the struggle of being chronically single. And it’s pretty obvious why. The modern dating scene is a battlefield full of failed talking stages, situationships, endless swiping, ghosting, and even breadcrumbing. Getting to the other side of it without major emotional damage is becoming almost impossible these days.

If the chill-inducing dating terms haven’t convinced you yet that romance has become pretty depressing nowadays, we invite you to take a peek at these conversations people overheard about dating from the ‘Overheard Dating’ Instagram page. They’re guaranteed to make you feel sorry for those who have to endure the search for a partner in these trying times. To find the juicy dating gossip, all you have to do is scroll down.

While you're at it, don't forget to check out a conversation with dating experts Kate Taylor, Jolene Beaton and Celine Ikeler from It's Dating Explained and Paige Dempsey, who kindly agreed to talk with us more about the modern dating scene.

#1

Dating-Funny-Conversations-Overheard

overhearddating Report

Mike F
Community Member
1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

With the theme from Mission Impossible (the old one) playing in the background.

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    #3

    Text post showing a funny conversation about dating and being single at Thanksgiving, highlighting humorous dating talks.

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    Gwen
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Just tell them that due to increased tariffs, they can either get gifts for Christmas, or you can be dating. Because with this economy, they can only choose one.

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    Dating experts describe today's dating scene as back-to-front, messy, but still exciting and full of possibilities.

    "I meet a lot of singles who are very happy to have [intercourse] with someone they met that same day, but who’d die before they sent two texts in a row. Honestly, that’s not how we’re designed to date. Early [intercourse] makes relationships more complicated than they need to be because it’s very hard — for women especially — not to bond with a intimate partner," dating coach Kate Taylor told Bored Panda.

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    "I wrote a whole book on this, called Not Tonight, Mr. Right. We like to think we can have fun, meaningless [intercourse] with anyone who catches our eye, but then we spend the whole of the next day preoccupied with whether or not we’ll hear from them again, even if we didn’t like them, or the [intercourse], that much."

    So the solution seems to be getting to know the person first before diving into bodily pleasures.

    "We try to appear nonchalant and unbothered, which is SO hard when [intercourse] has caused every attachment hormone - like oxytocin and vasopressin—to flood your system with 'Pick me! Love me!' vibes. Postponing [intercourse] makes dating really simple," Taylor explains.

    #4

    Conversation about dating where one person jokes about drinking every time a podcast was mentioned on their date.

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    Nadine Debard
    Community Member
    1 month ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    Girls. This is dangerous to get drunk around people you don't know well. OP should not assume that she'd be fine. Take care and keep safe. Edit: well it's not OP after all, it's whomever OP heard, but the message stays the same.

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    #5

    Conversation snippet about a disappointing date shared in hilarious dating conversations overheard by people.

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    Multa Nocte
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    "I can't believe I shaved my legs for this." ;-)

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    "In short, kind of a mess. But also kind of exciting," says dating coach Paige Dempsey, describing the modern dating scene.

    "People are growing tired of the dating apps and the old ways of dating aren’t working anymore. Women are getting smarter about what they are looking for in a partner and are no longer entertaining mediocrity or trying to ‘fix’ men.

    They pay attention to red flags and exit potential relationships earlier that aren’t aligned with what they want. That means the dating cycles become shorter when you realize that the person isn’t going to be a good fit for you."

    #7

    Text conversation about living with a boyfriend, featuring a humorous take on dating and relationships.

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    sturmwesen
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I hate the nearly empty/empty ice tray with a passion. we have space for about 6..can't you refill before we are down to 2 cubes?

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    #8

    Humorous conversation overheard about dating involving divorce papers at a Starbucks near Harlem 125th street.

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    Earonn -
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Clever move on her part. Do it in public, where others can intervene.

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    But the sister duo and dating experts Jolene Beaton and Celine Ikeler from It's Dating Explained, remain helpful about modern romance.

    "We think the dating landscape today is exciting and full of possibilities. People are investing in themselves more than ever, showing up with greater self-awareness and transparency about who they are and what they want. Across all ages, men and women are embracing confidence in the idea that they can meet someone and build a relationship with real potential to last!"

    #10

    Text conversation about a dog training book helping with effective communication in a relationship, from dating eavesdropper.

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    Mel in Georgia
    Community Member
    Premium
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Reminds me of the Southpark episode where Cesar the dog whisperer trains Cartman to behave ...

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    #11

    Text conversation about not being in the mood for dating and confusion between medication and dating apps in a humorous context.

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    Marina Muller
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Ive been on lexapro… it does k**l the mood for most things.

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    #12

    Text message conversation about dating where one person admits breaking up with their boyfriend after going outside to breathe.

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    We can always have hope, but reality is that a lot of people struggle with finding a compatible partner nowadays, and one of the reasons, according to experts, is the pool of options that is accessible to us.

    "Dating apps give everyone a much bigger dating pool to fish from. But they can also make us less keen to commit, because we feel we’re always only one swipe away from finding someone 100x better," Taylor says.

    "I don’t feel humans are wired for that amount of choice. We’re designed to find a nice partner from a social group of around 150 people. This feeling of choice makes us more likely to ghost, breadcrumb, or micro cheat."

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    #14

    Text excerpt from a humorous dating conversation accidentally eavesdropped on, revealing unexpected self-discovery.

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    Andrew Keir
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    It's a spectrum, not a binary decision. Being "a little bit gay" is fine.

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    #15

    Guy at a cafe on the phone expressing frustration about dating and wanting to be in love despite challenges.

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    Mel in Georgia
    Community Member
    Premium
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    If BP posts are any indication, this is very, very true.

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    Another reason why many folks are chronically single may be because our lifestyles have drastically changed and it has yet to be reflected in the dating world.

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    "For most of history, women needed a partner to provide for them. Now, women are able to provide for themselves in a way that was never available before. So women are looking for a true ‘partner’, not just a ‘husband’, and sometimes those two outcomes can be different," Dempsey explains.

    "We’re also coming off the tail end of a pandemic. Life changed. People got comfortable working from home and being at home. Finding a partner starts with putting yourself out there, and that can be uncomfortable," she notes.

    "Getting to know a whole new person is a cycle that used to happen more organically – for example, through work, school or activities – and now it takes a real effort to get to know someone and people are tired of starting over and over again."

    #16

    Text of a humorous dating conversation about making professional contacts instead of finding a boyfriend on dating apps.

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    Nadine Debard
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Lawyer, doctor? What app is this? Asking for a friend.

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    #17

    Text of a humorous conversation about dating where one person breaks up, saying they've already met someone better.

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    Noel Muller
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    It's weird how these posts really give a sense of the differences between NY, LA, and SF

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    Experts also noticed that people don't give enough of a chance to people, a mistake that is made by many.

    "Many singles dismiss potential matches after just one meeting instead of going on a second date, where true compatibility often begins to show," Beaton and Ikeler say.

    "Dating online, they’ll often set really strict dealbreakers about things that don't matter — like height, education, or eye colour. Lasting relationships are built on shared interests, mutual goals, kindness, honesty, and trust - not whether or not your partner can change a lightbulb without a ladder," Taylor adds.

    "So set one or two dealbreakers (I’d suggest location and age) but be willing to meet as many people as possible, even if they’re not your 'type.' Most people end up with a partner who’s very different from the sort of person they imagined settling down with, but who makes them the happiest they’ve ever been."

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    #19

    Text message about dating struggles in Los Angeles, highlighting humorous conversation about dating and relationships.

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    Ray Ceeya (RayCeeYa)
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    WOW! That is so oddly specific that I think I may have met that woman before!

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    #20

    Text about dating on Hinge app, joking about getting groceries while on unsuccessful dating trips at the farmers market.

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    DowntownStevieB
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    And, you can likely ditch them and say you just got "separated"

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    To make it easier to find lasting relationships, Taylor suggests making an effort to meet new people online and in real life.

    "Dating apps are great for introducing you to new people, but don’t overlook the people who are around you every day. The more you practise chatting to new people, the easier it'll get," she says.

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    "Also, delay physical intimacy as long as you can, but definitely until you’re officially dating. Having intimate relationships before you know what someone is really looking for is the best way to avoid getting emotionally committed to a situationship."

    #23

    Text post sharing a funny conversation about dating and social media success from people accidentally eavesdropped on.

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    #24

    Text post showing a humorous dating conversation about honesty and being a work in progress on a first date.

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    Andrew Keir
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Twenty-thee years later she gets an unexpected letter - "You are cordially invited to the funeral of ****** ..."

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    Meanwhile, Beaton and Ikeler advise finding a support group of single friends.

    "Get out there and have some fun with them. Everyone needs a good wingman. Get your mindset right so that you are in a good place and have the capacity to meet people. And then put some intention into your search.

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    And unfortunately, we hate to say it, but it may not happen naturally, you have to be proactive these days."

    #25

    Funny conversation about a situationship and IKEA furniture, showcasing hilarious dating moments overheard by people.

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    Nadine Debard
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Oh gosh. I hope he charges her for his services when she dumps him as soon as she doesn't need him anymore.

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    #26

    Text conversation about dating anxieties involving a rural boyfriend's hometown with no Whole Foods mentioned.

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    Ray Ceeya (RayCeeYa)
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I was born in a "Rural" town. it was four hours to a McDonalds. That's the Rural mountains of Eastern Oregon.

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    #27

    Manager asking employee to remove Bumble dates from work calendar in a funny conversation about dating overheard at work.

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    Andrew Keir
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    "But they *are* my work calendar ! "

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    Lastly, Dempsey encourages the singles out there not to give up.

    "You’re not too old. You’re not too whatever you think is holding you back from finding a relationship. You have to understand that a lot of people aren’t going to be the right fit for you – and that is okay. You want to be clear on what you’re looking for so you stand out and call in the right people. Don’t be afraid to be yourself, so you can find someone who is looking for someone like you," she concludes.

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    #29

    Text post showing a humorous conversation about a breakup, part of hilarious dating conversations accidentally eavesdropped.

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    Mel in Georgia
    Community Member
    Premium
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    It's the (lack of) thought that counts?

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    #30

    Conversation about dating where one person wants a man not dating nine other people.

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    Kris
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    A man who is not looking for a mom 😂

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    #31

    Screenshot of a humorous dating conversation tweet about cultural respect and podcast invitations, part of funny dating eavesdrops.

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    My O My
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    How awfully true this is for far too many people

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    #33

    Text conversation about dating mentioning age and Gen X emojis in a humorous overheard conversation about dating.

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    Mike F
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    D@mmit! My wheelchair emoji won't post.

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    #34

    Text conversation humorously describing adopting a rescue as a dating-related awkward, newly rich 30-something with poor social skills.

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    Miki
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    "newly rich". I think I know what she likes about him.

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    #35

    Conversation about dating commitment and Instagram post shared, highlighting funny dating moments accidentally overheard.

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    Mel in Georgia
    Community Member
    Premium
    1 month ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    My old-fashioned dad had a serious talk with me before I moved in with my long-distance BF (now long-time husband) about how it might ruin my "reputation" if it didn't work out. I literally laughed in his face.

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    #36

    Text of a humorous conversation overheard about dating, featuring a playful tip involving calling Con Ed for firemen as a way to cure loneliness.

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    My O My
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Question: what kind of firemen? Like the Australian calender ones? - asking for a friend

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    #39

    Couple in a humorous dating conversation where boyfriend says he has a headache and blames girlfriend.

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    Chris the Bobcat
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I just take some Tylenol. I'm already autistic, so I'm immune to the side effects.

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    #40

    Text conversation about dating with a humorous twist overheard in a funny dating conversation snippet.

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    #41

    Hilarious conversation about dating where boyfriend offers a hug and girlfriend threatens to pour alfredo sauce.

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    Adam Zad
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Then I'll suffer from Impasta Syndrome.

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    #42

    Hilarious conversations about dating with a funny exchange about prayer and losing a boyfriend.

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    Kim Steffen
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    It almost sounds like a Henny Youngman joke. (Cue squeaky violin).

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    #43

    Text conversation humor about dating with a person saying they love all three of their boyfriends.

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    Kris
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I find it exhausting to relate to one person. Imagine having to relate to three! I need my alone time

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    #44

    Text post with a funny conversation about dating, mentioning a breakup over calling something a me-me.

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    Andrew Keir
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    What on earth was he talking about? Or maybe I just don't want to know ...

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    #48

    Funny dating conversation about vague job titles and unexpected replies shared on a popular eavesdropping social media account.

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    Michael Largey
    Community Member
    1 month ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    Not someone I'd grow founder of with time.

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    #49

    Text of a funny dating conversation mentioning 54 Bumble matches and 6 promising ones, relating to dating humor.

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    #50

    Text showing a humorous conversation overheard about dating, mentioning an open relationship situation.

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    Mike F
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Sorry, above my paygrade. How about some seedless grapes?

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    #51

    Conversation snippet about dating with a guy warning about falling in love and a girl complimenting his confidence.

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    Adam Zad
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I've never heard that. Of course, I'm 6'9" tall when I'm wearing my six-inch, spike-heel, thigh boots.

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    #52

    Text post about a Bumble dating profile humorously saying good taste in alcohol but poor taste in men.

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    Owen
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Depends on the beard. Neatly trimmed? Might be good, that shows attention to detail. Hobo beard? Just keep walking. Neck beard? Maybe run away. Moustache only? An obvious warning sign.

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    #53

    Text screenshot of a girl telling friends about her boyfriend in a hilarious conversation overheard about dating.

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    Tonyah Mcanelly
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    But we will be seeing Coldplay tonight . LOL

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    #54

    A humorous conversation about dating where one person describes their ideal type as tall and having anxiety.

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    LinkTheHylian
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    D**n. So close. I've got the anxiety part down pat.

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    #55

    Text of a funny dating conversation about trust and funds, part of hilarious conversations overheard about dating.

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    #56

    Text exchange showing a funny conversation about manifesting and visualizing friends breaking up in dating talks.

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    Miki
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    This person must be Polish :D there are jokes about that type of thinking we do.

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    #57

    Text conversation about love and dating, capturing a humorous and relatable moment in modern dating culture.

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    #60

    First date conversation quote about pretending to pay and googling net worth from funny dating conversations.

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    Andrew Keir
    Community Member
    1 month ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Hint to OP - AI is notoriously bad at numbers

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