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Alright, buckle up! We’re diving into a wild collection of funny-but-ouch moments when someone close tried to be funny and... well, missed a bit. Here come 41 stories where jokes stung, compliments backfired, or just plain weird stuff was said. Let's get to it!

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#1

Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

thatonepersoniam , Curated Lifestyle Report

At a party, this girl asked me to fake-date her so some guy would buzz off. We actually had a blast and went on a real date later. After that, she dropped "you're a great fake boyfriend." Ha! Meant as a joke, but ouch - kinda an odd thing to hear after a great date. Years later, we’re married and I call her my "great fake-wife" sometimes for laughs.

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    #2

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    misguided-ghost-365 , Laura Siegal Report

    In middle school, my fave teacher was teaching WWII and casually dropped, "Do you guys know what Jews look like? They have dark hair and big noses, like [my name]." Whoa. That hit like a ton of bricks. I'm not even Jewish and never cared about my nose - until then.

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    #3

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    schmody18 , Sheikh Nayim Hasan Report

    My nephew once guessed I was 36. Um, I was 24. Thanks for making me feel ancient, kid.

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    A little while back, Reddit user u/austerbear asked the AskMen community: “Fellas, what’s something a loved one said to you that was meant to be funny or playful but kinda hurt?” And boy, did the answers flood in! Lots of awkward, hilarious, and head-scratching moments from partners, friends, coworkers, and even kiddos.

    Turns out, humor is tricky. What’s funny to one person might feel like a smack in the heart to another. So grab a snack and dive in with us - you might even spot yourself in these!

    #4

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    BearonVonFluffyToes , Tamara Bellis Report

    Every time someone new meets my wife, they joke she’s way too pretty for me. There’s that cheeky comment about blackmail or that I’d better shape up so she doesn’t leave. Said with smiles, but dude, it’s not exactly a knee-slapper to my confidence.

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    #5

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    BalboBigggins , Andrej Lišakov Report

    My buddies bragged about a theme park having a “Craig free day.” Uh, yeah? I’m Craig. Kinda funny but also, ouch, dude.

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    #6

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    02silverado53 , Scott Blake Report

    People ask what I’m up to and I say construction work. Cue, "What do you REALLY want to do?" or "You’ll find something better." I actually love my job, but it still sometimes feels like I’m getting a pat on the head for aiming low - even from my own mom. Oof.

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    First off, everyone’s comedy radar is different. What cracks one person up might totally flop or sting for another. Cultures, backgrounds, and just plain personal quirks make humor a minefield.

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    Plus, not everyone’s a detective of feelings. Some folks notice every tiny facial twitch, others miss clues even when they’re flashing neon signs. Cue awkward moments.

    #7

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    GarriSenpai , Kaleidico Report

    My close friend was playing matchmaker and said, “If it doesn’t work, it’s cool. You aren’t the most attractive either.” Yikes. Since I was already doubting myself post-breakup, that stung. We ended up hooking up though, so I got some sweet revenge.

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    #8

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    LAKingsDave , Andrej Lišakov Report

    I was gaming with friends and there was another Dave. This girl jokingly called me “evil Dave.” I asked why, got zero answers. Like, what did I *do*? Trying to be a good guy and here comes the evil label. That one stung a bit.

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    #9

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    Shaddow1 , Curated Lifestyle Report

    After I broke up with my ex, my best friend said, “I was hoping it’d work out - you’re kind of un-datable.” Probably a joke, but dang, it hit me deep. Like, thanks for the confidence boost?

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    Blame it on the TikTok era? Some think our emotional radar is getting rusty because we spend so much time texting and scrolling instead of face-to-face chit-chatting. Pixels don’t give off much vibe.

    So, what’s funny can get lost (or hurtful stuff might sneak through), especially when people forget how to read the room. It’s a wild ride!

    #10

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    anon , Andrej Lišakov Report

    I’m super sensitive about my weight. When my wife once joked about it, I nearly lost it. I told her, “You’re supposed to have my back! If you make jokes about this, I don’t know if I can deal anymore.” Some things just hit home harder from the people you love.

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    #11

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    downloadmymerch , Getty Images Report

    My buddies and I have a ton of playful trash talk going on. During a mountain trip, someone said, “I’m not sure I can handle a whole weekend with you.” We laughed it off but yeah, those words kinda stung each time I thought about them later. Snowball fights and all, but still.

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    #12

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    Smoking_Fire , Pablo Merchán Montes Report

    Got hit with the compliment, “You’re not THAT ugly.” Yeah... thanks? Not exactly a confidence booster but hey, I guess it was meant as kinda funny.

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    Why do some people nail the joke while others look like dad at the dance? Probably a sprinkle of natural wit, a pinch of risk-taking, and a dash of knowing your audience.

    Some comedians even swear by the “laugh at yourself first” trick. If you can joke about your own quirks, no one can throw shade at you (or they’ll just join in).

    #13

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    quokka29 , Getty Images Report

    A close friend teasing me about being mixed ethnicity, like “you’re half this or half that.” Ouch. I’m dealing with trauma about it. It’s the kind of thing that feels small but hits below the belt.

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    #14

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    RyGuyMcDaddy , Getty Images Report

    My metabolism’s so high I've been trying everything to gain weight and I’m still underweight. My family keeps joking I’m “too skinny” like I have some eating disorder. Every holiday it gets louder. I tell myself I’m used to it, but yeah, it still stings.

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    #15

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    numbah12345 , Priscilla Du Preez 🇨🇦 Report

    I asked my girlfriend why she wanted to be with me. She said it was because she’s afraid of change. Yeah, that hit a little weird in my chest.

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    Anyway, whether this list teaches you emotional smarts or just gives you a chuckle, it’s a fun ride through real human moments. So, read on, laugh a little, and maybe share your own “oops I didn’t mean that” stories below!

    #16

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    edibleroach , kues1 Report

    One of my (former) best friends kinda recoiled, said “UGH! GROSS!” when someone asked if we were dating. Oof, talk about a burn from someone close.

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    #17

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    putnamto , Lia Choi Report

    My dad, after a few drinks, said, "Even though I know you’re never going to amount to anything, I will always love you." I’m 32 now, still in a crap job, living in his crummy house. Thanks for the pep talk, Dad.

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    #18

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    WriteSomethingGood , Vadim Sherbakov Report

    My girlfriend keeps reminding me I dropped out of University. She works at a school and claims I’m proof you don’t need a degree to make it. I’m all for that, but dude, could you not bring it up every time?

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    #19

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    ASHarper0325 , Jakub Kapusnak Report

    Friends have been calling me “Egg” for years because of my head shape. I’m mostly okay with it now, but when depression hit hard, that nickname wasn’t exactly comforting.

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    #20

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    anon , OurWhisky Foundation Report

    My real laugh sounds like the Batman theme - ”Na Na Na Na Na Na Na Na.” People always point out my weird laugh and then I try to shut it down for the night. Not cool, man.

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    #21

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    CodeBlue0817 , Getty Images Report

    Anything about my teeth stings. I couldn’t afford braces growing up. No amount of jokes about my smile ever made it easier to shake off.

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    #22

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    mitcheg3k , Nappy Report

    My brother once joked, "Good luck being painfully average - with your average-looking wife, dead-end job, and a mortgage for life." If only he knew that my biggest fear is being unremarkable. That comment echoes in my head every single day.

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    #23

    shoetshirt23 Report

    I had an epileptic seizure and my girlfriend joked she’d leave me now. Joke or not, that one punched a hole in my heart.

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    #24

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    Talbotsunbeamer , Getty Images Report

    I’ve had tooth troubles for years. At a family gathering with Chinese food, I reached for a rib and heard, “You don’t want to bite into that, not with your bad teeth.” That was 14 years ago, and I still wince. Good news: my teeth are fixed now!

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    #25

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    anon , Getty Images Report

    She joked, “You wouldn’t get it because you’re an immigrant.” I knew it was a joke, but I’ve always struggled with my identity. That phrase felt like a slap across all my efforts to fit in.

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    #26

    Somedudewithahotdog Report

    I’ve always sang and played guitar. People say I have a good voice, but my ex drunkenly told me I was a bad singer. That punched my confidence and still creeps into my head whenever I sing - even alone. Thanks, ex.

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    #27

    bluelemon0219 Report

    Almost 30 years ago, my husband told me I had big ears. I still think about it whenever I pull my hair back. That stuck way longer than it should have.

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    #28

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    FleurDeFuck , Gabriel Ponton Report

    My then-partner was laying out their grand plans to change the world, then dropped: "And then there’s you. You just want to be loved." Felt like the definition of me was just being the lonely half of a couple, easily brushed aside. Blast my existential crisis later.
    But hey, not everyone has earth-shattering dreams. Sometimes wanting to be happy and loved is enough.

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    #29

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    mamamiax94 , Mélanie THESE Report

    Female here. I told my fiancé he looked like Woody from Toy Story. Saw the sting but now he calls himself my Woody for life - guess I didn’t hurt him too bad?

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    #30

    nunezhurtad Report

    Got called a little girl for showing my soft side. Sensitivity doesn’t get much respect sometimes!

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    #31

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    TheKhun , Minh Ngọc Report

    I’ve learned to live with my nose but every time someone pokes fun at it, I feel a big “oof” inside. It’s like they poke a bruise I didn’t know was still tender.

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    #32

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    anon , Getty Images Report

    Growing up, my mom kept saying she never wanted to make with me the mistakes she made with my brothers. Said it daily for years. Asked her to stop but she never did. Felt like a constant reminder I was a mistake.
    She had bipolar disorder and rehabbed many times. Family stuff gets complicated.

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    #33

    SirWhanksalot Report

    A friend once joked, “I think you’re going bald soon.” Now it’s stuck in my head and I think about it all the time.

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    #34

    ThatDudeUpThere Report

    My sister once said, “Whoever thought that dude would be the breadwinner out of us?” That was over a decade ago. Well, still the least successful out of us three! Zing!

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    #35

    Dredgeon Report

    My big dream is to be a racecar driver, even though I doubt myself a lot. So when people joke about my driving, it hurts - I’m reminded of my own insecurities.

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    #36

    srgbski Report

    In private, she raves about my size and skill in bed. With her friends? Little jabs and remarks. At first, I thought she just didn’t want her girlfriends hitting on me, but that wore off and now it’s just painful.

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    #37

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    Firehawk157 , Mike Erskine Report

    My teen son roasted me around a campfire at a family friends' place. They’ve known him forever and he’s usually shy. Proud he opened up, but ouch - he called out my real flaws as a dad and person. Definitely hit differently hearing it out loud from the kid I’m trying not to be like.

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    #38

    LMtOSU Report

    My ex drunkenly said my roommate/good friend was very attractive. Normally, I wouldn’t care, but the fact she never complimented me hurt all night.

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    #39

    Wait, They Actually Said That?! 41 ‘Jokes’ From Loved Ones That Totally Missed The Mark

    Bigmace_1021 , Towfiqu barbhuiya Report

    I’m 19 and super skinny (~110 lbs). Almost everyone I meet tries to pinch my wrist and see how tiny I am. I'm not hurt but yeah, it gets old fast.

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    #40

    Hawgster Report

    Got told, “Oh you’re a virgin, I have a lot I can teach you.” Yeah, thanks for the subtle humiliation.

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    #41

    IcariusFallen Report

    I was talking to this girl seriously. One day she texted she was bored and I said, “Aw, you missed me?” She replied, "I missed your c**k; after all, I’m just with you for really good sex." Ouch. Being just a sexual object hurts, especially with someone you care about.

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