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Anyone who is currently dating knows how difficult and confusing the process can be. On the one hand, you’re excited to meet new people! On the other hand, some of those people turn out to be so cringy, creepy, or clingy that you can’t wait to vent about them.

Bored Panda has curated this list of the biggest dating disasters and awkward fails to show you just how bad things can get. Scroll down to check out these people’s stories, but be warned, some of them come with a big side-order of secondhand embarrassment. It’s enough to make you glad that you’re already in a relationship or to swear off dating altogether.

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    #2

    That's Wild

    Tweet about a painful but hilarious date fail where a blind date stayed silent and canceled afterward.

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    Sally Moen
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    She got a replacement by offering a free meal

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    #3

    This Waiter Is My Hero

    Tweet sharing a painful but hilarious date fail where a man juggled two first dates at a restaurant.

    see_kel Report

    What you (think you) know about dating, successful relationships, and ‘perfect’ partners might just be wrong.

    Based on the findings of a study published in the Proceedings of the National Academy of Sciences, your own judgment of your relationship reveals more about its quality and success than your or your significant other’s personality.

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    #5

    The Bro Code Kicked In

    Tweet showing a humorous and painful date fail involving a waiter hiding expensive drinks, illustrating awkward social moments.

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    Abel
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    He was not a waiter. He was a guardian angel!

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    In a nutshell, how appreciative you are of your partner, and how satisfied you feel your partner is with you, are more important than who you both are as individuals.

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    The vital things are the effort you both put in, your commitment, appreciation, satisfaction with your intimate life, perceived satisfaction, and how you handle conflict.

    So, instead of obsessing over whether your significant other checks all or most of your boxes, you should focus on engaging with them.

    #7

    And That's How I Met Your Mother

    Text post about a painful but hilarious date fail where a girl introduces her new date to her ex-roommate.

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    Lotekguy
    Community Member
    Premium
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Well that's a time saver. The ex would have told her all the worst things about you so that it wouldn't have lasted, anyway.

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    #8

    This Is Actually Hilarious

    Screenshot of a social media post describing a painful but hilarious date fail involving a framed photo on a first date.

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    Abel
    Community Member
    4 days ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    You are no match between the love of a person and their pet!

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    “When it comes to a satisfying relationship, the partnership you build is more important than the partner you pick,” the study’s lead author and an assistant professor at Western University in London, Ontario, Samantha Joel, told CNN.

    “It seems to me that the relationship is more than the sum of its parts. It’s that relationship dynamic itself, rather than the individuals who make up the relationship, that seems to be most important for relationship quality.”

    #10

    Suggested A Date, Got A Lecture

    Text message exchange showing a painful but hilarious date fail discussing first date preferences and misunderstandings.

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    The Other Guest
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Any place that a) you can talk without disturbing others and b) has things there that you can talk about, is a great place for a first date. Museum, arboretum, zoo, aquarium, county fair, etc etc. are all good choices.

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    #12

    He Started Crying

    Screenshot of a social media post sharing a painful but hilarious date fail where a date started crying unexpectedly.

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

    Sounds pushy and unbalanced. OP dodged a bullet. I've seen that kind of manipulation before. From the man who r@ped me.

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    Many people try to come across as better than they really are on first dates. It’s natural. Most of us want to leave a positive first impression on the strangers we meet.

    And yet, this means that you might not get to grips with someone’s real character, quirks, and flaws until much later into dating them, because they’re actively trying to hide them.

    #13

    Text post sharing a painful but hilarious date fail involving a disappointing first date at a local brewery.

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    Lotekguy
    Community Member
    Premium
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    You handled it very well, taking care of the interests of both parties.

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    #14

    Happy Ending

    Screenshot of text describing painful but hilarious date fails including awkward encounters and unexpected reactions on dates.

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    HF
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    well, it's much easier when the date is already your wife

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    #15

    At Least You Realized Before It Got Too Far

    Screenshot of a humorous online comment revealing an awkward family-related date fail.

    LKWSpeedwagon Report

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    Luckily, some people are so awful at leaving good first impressions that you can instantly recognize their red flags and problematic behavior patterns.

    Though this leads to awkward and embarrassing encounters, this is actually a good thing. Why? Because you instantly realize these individuals are worth avoiding. And so, you won’t waste any more of your precious time dating them.

    #16

    Like How Does That Happen

    Tweet discussing a painful but hilarious date fail involving a Tinder date and an awkward wedding dress moment.

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    Phantom Phoenix
    Community Member
    Premium
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Amicable with his ex-wife. Green flag. Don't know the circumstances around getting OP involved on their first date. Can't determine that flag's colour.

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    #17

    Mistakes Were Made

    Social media post showing a painful but hilarious date fail where someone was publicly complained about during the date.

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    WindySwede
    Community Member
    4 days ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    "Accidentally"?

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    #18

    Man Found Exactly What He Wanted. Talking Stage Is Not Necessary

    Tweet about painful but hilarious date fails where a first date involved measuring a ring finger with tape and second date had a tattoo incident.

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    Phantom Phoenix
    Community Member
    Premium
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    You know that everyone who's asked about the tattoo is told that she's his crazy ex girlfriend

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    The Guardian notes that some of the worst things people can do to leave a bad impression on a first date include things like arriving late, canceling the date on short notice, or even not bothering to turn up with no warning.

    Other things that might push your potential partner away are things like looking wildly different from your dating profile photo, complaining a lot, and whining about being exhausted.

    #19

    People Do Weird Things

    Screenshot of a hilarious and painful online dating fail where a girl reveals she eats a book with frayed pages.

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    Galita
    Community Member
    Premium
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    At least you know your library is safe, if the book is not to her taste.

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    #20

    Ohh

    Text post describing a painful but hilarious date fail where a racquetball hit the date twice in the face.

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    Robert T
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I assume you mean with the ball, otherwise that's just rude!

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    #21

    Not The Paper

    Tweet about a first date hiking adventure that turned into a rescue, illustrating painful but hilarious date fails.

    thatstelladoe Report

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    Other alarm-worthy first-date behaviors are things like criticizing your food, insisting on ordering for your date, constantly talking about yourself, whining about your ex-partners, and being overly sarcastic.

    You also won’t leave a good impression on your date if you are too self-deprecating, boast about not being like other people, are not curious about them at all, or agree with absolutely everything they say.

    #22

    Sounds Like He Was Desperate Not To Let An Expensive Trip Go To Waste

    Screenshot of a painful but hilarious date fail where a man nearly proposes on a first date after a broken engagement.

    crazycatlady331 Report

    Lotekguy
    Community Member
    Premium
    4 days ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    The reddest of the red flags would be if the ticket to Aruba was one-way, rather than round trip.

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    #23

    Screenshot of a social media post describing a painful but hilarious date fail where one person talks only about their tractor.

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    Zig Zag Wanderer
    Community Member
    4 days ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    🎶Oi got a brand new combine harvester, an oi'll give you the key... 🎶

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    #24

    Text post showing a funny and painful date fail where someone calls their date by the wrong name.

    i_heart_kermit Report

    Lotekguy
    Community Member
    Premium
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Are you sure? Maybe you got your name wrong. Check a couple of sources of ID.

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    Some relationship red flags indicate that your date might be a truly toxic individual. WebMD warns that some of these toxic personality traits include controlling behavior, causing drama, behaving inconsistently, craving attention, and not being able to be happy for you.

    A good rule of thumb is to avoid people who confuse you with their behavior, make you feel uncomfortable, and who you feel are manipulating you.

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    #26

    Text post from 10 years ago about talking about avocados for an hour, illustrating painful but hilarious date fails.

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    Sara Frazer
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    The username has reminded me that I have a fresh pack of strawberries and a fresh jar of Nutella in the kitchen... it may soon be Nutella time for me... 🍓

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    Which of these posts about dating fails made you wince and cringe the most? What is absolutely the worst date that you’ve ever been on? Have you ever embarrassed yourself on a first date? What are your top relationship red flags?

    On the flip side, what’s the best date you’ve ever had? If you’d like to share some of your experiences, we’ll be waiting to read them in the comments at the bottom of this list.

    #28

    That's Actually Kind Of Cute

    Tweet about a painful but hilarious date fail where the date forgot what their partner looked like in the restaurant.

    _Cx2_ Report

    #29

    I Was So Embarrassed

    Tweet from a woman describing a painful but hilarious date fail where the man fell asleep on a restaurant patio sofa.

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    Abel
    Community Member
    4 days ago

    This comment has been deleted.

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    #32

    When They Say Men Are Blunt

    Tweet showing a painful but hilarious date fail where a man mistakenly thought his date was her sister.

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    #33

    Oh No

    Social media post describing a painful but hilarious date fail where spit accidentally lands on a date’s black shirt.

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    azubi
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    "Now we exchanged fluids anyway, do you think we might..."

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    #35

    $5 Uber Request For First Date

    Text message conversation showing a confusing and painful but hilarious date fail with mixed signals and cancellation.

    richpinta Report

    Michael Largey
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I've got a prior commitment that I'll make as soon as we hang up.

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    #36

    I'm "Trying" To Date And I Encounter This Constantly. Why Is It Such A Big Deal That I Choose Not To Drink Alcohol?

    Text conversation showing a hilarious and painful date fail about drinking preferences and awkward first meeting ideas.

    DarthSadie Report

    Zig Zag Wanderer
    Community Member
    4 days ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    I can never understand people who can't understand people who don't drink. I mean, I don't do crack, but nobody finds it weird. What's with the need for people to drink? (I drink, but don't care if others don't)

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    #38

    It Was A Gas Station Near Her So She Could Easily Walk Home

    Screenshot of a tweet describing a painful but hilarious date fail involving an accidental text from a date calling someone ugly.

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    Michael Largey
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    One time spending money on a lottery was a guaranteed win.

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    #39

    A Real One

    Tweet showing a date fail where someone got arrested after giving a waitress a side eye, illustrating painful but hilarious date fails.

    HugItOutAlready Report

    Lotekguy
    Community Member
    Premium
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    What a lucky break. It saved you the trouble of having to drive her home.

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    #40

    Super Disrespectful And Flakey

    Screenshot of a painful but hilarious date fail tweet about showing up 3 hours late claiming to be a pageant queen.

    MNCVKG Report

    Sally Moen
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    What were you doing waiting for them? Why?

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    #41

    "Here For A Good Time Not Long Time"

    Tweet showing a painful but hilarious date fail about ice skating and Tinder profile photo update.

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    Ace
    Community Member
    Premium
    3 days ago

    This comment is hidden. Click here to view.

    And?

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    #42

    Reddit user shares a painful but hilarious date fail of being stood up after a dance 30 years ago.

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    #43

    I Asked If She Would Split The $350 Sushi Dinner She Wanted For The First Date

    Text message conversation showing a harsh and hilarious date fail involving rude and blunt rejection.

    Boring_Mango1098 Report

    Richard Smith
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Wow, best of luck to the "successful man" who gets cleaned out by her.

    #45

    She Really Didn't Want To Go On That Date

    Tweet about a painful but hilarious date fail involving a burned-down restaurant and a missed second date.

    DrdreGator Report

    Lotekguy
    Community Member
    Premium
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    If she committed arson to avoid the date, that's about the worst rejection I've heard of.

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    #46

    That's Just Heartless

    Screenshot of a humorous tweet describing a painful but hilarious date fail involving babysitting and leftover food.

    Larellj Report

    Abel
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I had to google what a "baby daddy" means, and now I am sad...

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    #48

    At Least He Tried To Be Funny

    Tweet describing a funny and painful date fail involving a man using two straws to pretend to be a mammoth on a coffee date.

    sehahaj Report

    #49

    Safe To Say The Date Will Not Happen

    Text message conversation showing a painful but hilarious date fail with awkward excuses and misunderstandings.

    VladislavThePoker_ Report

    Sally Moen
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I'm gonna say that to my boss next time they ask me for anything, should be fun

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    #50

    A Surprise Double Date

    Tweet showing a painful but hilarious date fail where someone showed up five months pregnant on a first date.

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    Phantom Phoenix
    Community Member
    Premium
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Are pregnant single women not permitted to enjoy some company?

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    #51

    Crazy Thing Is All Week We Were Vibing So Good On The Phone I Was So Excited For This Date

    Tweet from Tebello sharing a painful but hilarious date fail about someone showing up barefoot on a date.

    matyoloqueen Report

    #52

    She Will Always Love Him

    Tweet from Worst First Date about a painful but hilarious date fail involving karaoke and an ex dedication.

    worstfirstdate_ Report

    #53

    Interesting Question

    Tweet showing a painful but hilarious date fail where one person awkwardly asks about liking when guys throw up.

    VeinRichard Report

    Lotekguy
    Community Member
    Premium
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Just think how thrilled they'll be if they ever get a yes.

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    #55

    Screenshot of a painful but hilarious date fail where a girl discusses future plans on the first date, causing awkwardness.

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    OktopuS
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    It wouldn't surprise me if his mom had some involvement in that.

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    #56

    She Sounds Fun

    Screenshot of a social media post describing a painful but hilarious date fail involving a drunk date peeing beside a car.

    Bens_head_space Report

    Kristiina Männiste
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I actually had to interrupt a making out session, to run for the bushes in a restaurants parking lot.... (the restaurant was closed by then). Not drunk (dont drink alcohol) but when Im nervous, I keep sipping water. The waiter had to bring at least 2 extra jugs. And yeah... On my way back back to the car I noticed the "No peeing", "Video surveillance" signs....

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    #57

    I Would Of Face Palmed So Hard

    Tweet showing a funny date fail where one person confused Red Lobster for Outback Steakhouse, a painful but hilarious date fail.

    jimmyfallon Report

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

    "Throw another shrimp on the barbie." "Sir, this is Red Lobster, and stop calling me Barbie."

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    #58

    She Got The Ick

    Tweet about a painful but hilarious date fail involving earwax mishap during a first meal together.

    fesshole Report

    DaisyGirl
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    🤢🤮🤢🤮 how does this even happen?!?!

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    #59

    Oh My

    Text post describing a painful but hilarious date fail where a girl shares an awkward personal detail early in the date.

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    Captive
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Sounds like hidden cam to film the reaction

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    #60

    It's Something I Haven't Thought About In Years So Was Fun To Remember And Share

    Screenshot of a social media post describing a painful but hilarious date fail involving fainting at a Bette Midler show.

    zenny517 Report

    #61

    He Didn’t Market Himself Very Well. Did He?

    Tweet about a painful but hilarious date fail where a marketing executive was late and made awkward remarks.

    fesshole Report

    Ace
    Community Member
    Premium
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Isn't that from the Austin Powers movie? I could imagine an American trying (but failing) to make a joke and mimic Mike Myers' British accent could end up sounding like that.

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    #63

    Screenshot of a painful but hilarious date fail story about a language barrier causing awkward communication.

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    Richard Smith
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    That's unfortunate but understandable. Even with modern translation software/hardware language barriers are still very difficult.

    #64

    Ouch

    Text post describing a painful but hilarious date fail with a broken car A/C leading to awkward sweaty moments and an uncomfortable goodbye.

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    WhyamIhere?
    Community Member
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Aww man, nothing seemed too bad here except for the humidity and poor timing

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    #65

    She Definitely Needed That Foot Rub

    Screenshot of a tweet describing a painful but hilarious date fail involving a foot rub with a bad smell.

    Paynen_Sahrow Report

    Ace
    Community Member
    Premium
    3 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Why would you make such an offer? And c'mon, someone who's wearing boots for at least the length of a movie, you're not gonna get shower-fresh feet, are you?

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    #66

    I Just Messed Up Big Time

    Text post about a painful but hilarious date fail involving a mix-up with event tickets and a six-hour car ride.

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    #67

    Needless To Say, There Was No Second Date

    Screenshot of a social media post describing a painful but hilarious date fail involving spilled hard cider and a long walk home.

    aykshually_elsewhere Report

    DaisyGirl
    Community Member
    4 days ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Dont get not taking a taxi - that was just plain silly

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