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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

    He Started Crying

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

    Joyful-Sea-Lion Report

    Ray Ceeya (RayCeeYa)
    Community Member
    2 hours 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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    #3

    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
    2 hours 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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    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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    #4

    This Waiter Is My Hero

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

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    #5

    Not The Paper

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

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    #6

    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
    16 minutes ago Created by potrace 1.15, written by Peter Selinger 2001-2017

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

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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

    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
    1 hour 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.

    #8

    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
    3 hours 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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    “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.”

    #11

    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
    2 hours 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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    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.

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    #14

    Had To Pay To Give Legal Advice

    Tweet showing a painful but hilarious date fail involving unexpected family law questions throughout the date.

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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

    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
    1 hour 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.

    #17

    Happy Ending

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

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    #18

    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
    1 hour 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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    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

    Who Only Eats One Slice?

    Screenshot of a humorous social media post describing painful but hilarious date fails involving awkward outfits and rude behavior.

    etothepowerof3 Report

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

    You're a house? What exactly does that mean?

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    #20

    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
    1 hour 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.

    #21

    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.

    euphorixa 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

    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

    #23

    At Least You Realized Before It Got Too Far

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

    LKWSpeedwagon Report

    #24

    The Bro Code Kicked In

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

    masaun_k Report

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

    Imagine her getting matched with the guy who cannot imagine dating a non-drinker, and then realizing how much money you save by dating a non-drinker

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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.

    #25

    A Surprise Double Date

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

    stashafful Report

    Phantom Phoenix
    Community Member
    Premium
    2 hours 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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    #26

    That's Just Heartless

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

    Larellj Report

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

    O-kay? If you were done eating, and she DID ask

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    #27

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

    djse Report

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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

    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
    2 hours 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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    #29

    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

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

    Could be me. I have face-blindness.

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    #30

    Like How Does That Happen

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

    clur_sands Report

    Phantom Phoenix
    Community Member
    Premium
    2 hours 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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    #31

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

    ethereal_galaxias Report

    Zig Zag Wanderer
    Community Member
    2 hours 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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    #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.

    BeccaDelphia Report

    #33

    That's Wild

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

    sedore93 Report

    Sally Moen
    Community Member
    41 minutes 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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    #34

    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
    1 hour 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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    #35

    "Here For A Good Time Not Long Time"

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

    Drunk_by_10am Report

    #36

    Mistakes Were Made

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

    worstfirstdate_ Report

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

    "Accidentally"?

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    #38

    Send Help

    Screenshot of a social media post describing a painful but hilarious date fail involving a roommate joining the date unexpectedly.

    TogarSucks Report

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    #42

    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

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    #43

    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
    39 minutes ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    What were you doing waiting for them? Why?

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    #44

    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
    57 minutes 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.

    #45

    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.

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    #46

    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
    48 minutes ago Created by potrace 1.15, written by Peter Selinger 2001-2017

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

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    #47

    Suggested A Date, Got A Lecture

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

    Leadingman_ Report

    #48

    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

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    #51

    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.

    Paynen_Sahrow Report

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

    Try not letting who someone else is dictate who you are. The decent thing to do would be to calmly communicate your disappointment and drive her back to her home

    #52

    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
    50 minutes 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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    #53

    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

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    #54

    Probably Works There Now

    Screenshot of a Twitter post describing a painful but hilarious date fail involving a Walmart candy shopping incident.

    JonathanMcCall Report

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    #55

    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

    Chat GPT
    Community Member
    2 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Tbh I'd laugh so hard. What's wrong with him. I'll take him

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    #57

    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

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    #58

    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
    41 minutes 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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    #59

    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
    2 hours 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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    #60

    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

    #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

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    #62

    Oh My

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

    reddit.com Report

    OktopuS
    Community Member
    2 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    That last sentence is quite the punchline...

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    #63

    Only Three Haircuts

    Text post describing a painful but hilarious date fail involving mocked drink choices and leaving early after 20 minutes.

    aykshually_elsewhere Report

    #64

    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

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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.

    ShineiNozen Report

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    #67

    $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