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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.

#1

Text post describing a painful but hilarious date fail where someone vomited on a ride yet stayed together and got engaged years later.

Crashmaster007 Report

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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.

    sedore93 Report

    #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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    #4

    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

    #5

    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

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    #6

    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.

    Cooper35 Report

    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.

    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.

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

    #7

    Cool Ok Bye

    Reddit post sharing a painful but hilarious date fail about not getting movie tickets together and sitting apart.

    Safe_Regret_8592 Report

    #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.

    Feeling_Voice1053 Report

    #9

    Had To Pay To Give Legal Advice

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

    GoldenBoy407305 Report

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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.

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    “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

    Screenshot of a humorous online comment about a painful but hilarious date fail where he brought his mom.

    CaptainFartHole Report

    #11

    Suggested A Date, Got A Lecture

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

    Leadingman_ Report

    #12

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

    kkeesla Report

    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.

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    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

    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

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    #14

    Happy Ending

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

    Jessie_James Report

    #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

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

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    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.

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    #16

    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

    #17

    Mistakes Were Made

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

    worstfirstdate_ Report

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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.

    reddit.com Report

    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.

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    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

    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.

    Einjeth_ Report

    #20

    Not The Paper

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

    thatstelladoe Report

    #21

    Ohh

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

    safe_work_for_naught 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.

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    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

    #23

    Send Help

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

    TogarSucks Report

    #24

    Probably Works There Now

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

    JonathanMcCall Report

    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.

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    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

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

    nutellatime Report

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    #26

    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

    #27

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

    ethereal_galaxias Report

    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?

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    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

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

    i_heart_kermit Report

    #29

    Reddit user shares a painful but hilarious date fail involving awkward silence and unexpected revelations during lunch.

    BecksSoccer Report

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    #30

    Sorry What?

    Tweet describing a painful but hilarious date fail where someone dipped their hand into a drink and ate a berry.

    Sulflower_Rose Report

    #31

    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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    #32

    Social media post describing a painful but hilarious date fail where hair caught fire from a candle in a kitchen.

    guacaflockaflames Report

    #33

    Reddit user shares a painful but hilarious date fail about a restroom break and a bartender interaction.

    One-Cup-4337 Report

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    #34

    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

    #35

    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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    #36

    "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

    #37

    Oh No

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

    doubledribbl Report

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    #38

    $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

    #39

    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

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    #40

    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

    #41

    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

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    #42

    Tweet showing a painful but hilarious date fail where a blind date complains about her ex the entire dinner.

    ComedySeth1 Report

    #43

    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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    #44

    Tweet screenshot showing a woman sharing a painful but hilarious date fail where she left after her answers were written down.

    suzyeh73 Report

    #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

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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

    #47

    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

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    #48

    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

    #49

    Interesting Question

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

    VeinRichard Report

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    #50

    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

    #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

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    #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

    Screenshot of a painful but hilarious date fail involving moving day, rejection, and a saved WhatsApp conversation.

    reddit.com Report

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    #54

    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

    #55

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

    caveman7392 Report

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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

    #57

    She Got The Ick

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

    fesshole Report

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    #58

    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

    #59

    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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    #60

    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

    #61

    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

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    #62

    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

    #63

    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.

    WriteReflections Report

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    #64

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

    L_750z Report

    #65

    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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    #66

    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

    #67

    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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