29 Awkward Attempts to Be Funny That Went Hilariously Wrong

Turns out, people with dead moms aren’t the best audience for yo mama jokes
29 Awkward Attempts to Be Funny That Went Hilariously Wrong
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If you’re someone who loves to quote movies to your friends, be aware that movie quotes aren’t one size fits all. While quotes like “You can’t handle the truth” and “You talkin’ to me?” are relatively benign and unlikely to offend anyone, there are some that are much more precarious. Take this line from Dodgeball in which Vince Vaughn tells a group of Girl Scouts, “You’re adopted. Your parents don’t even love you.” While hilariously mean in the context of the movie, it’s not a quote you can just pull out anywhere.

One Redditor learned this the hard way when they said that line to a friend’s cousin at a family party. As it turns out, the cousin was adopted, and the joke teller was mortified and remembered it for years afterwards. 

Those are exactly the kinds of stories featured in this Reddit thread about times someone tried to make a joke that ended unbearably awkwardly.

Satyrane 8y ago A girl had what looked like a little spot of bean dip on her upper lip, and I jokingly said that she kinda looked like Hitler. She started crying. Turns out it was a permanent scar that happened recently. Another time I saw a girl crying at a party, and I just said Hey, it's okay. Guys are dicks. It was kinda my go-to before this when I saw crying girls at parties, and it usually cheered them up. Turns out her boyfriend just died in a car crash. So anyway, that's why I never talk to
el-toro-loco 8y ago I was at a party, and a girl behind me was talking with a mouthful of food. | couldn't understand her so I said, I could have sworn I just heard one of the adults from Charlie Brown. A few people laughed, and I didn't think much about it. Later on, the host of the party told me that she has a speech impediment.
cecebeme 8y ago This guy I work with showed us a picture of a buff shirtless dude on a motorcycle and said, this is what | want to be one day. So I said wow it's going to take you a long time to turn yourself into a motorcycle and he gave me the most evil look. It was around other coworkers as well and only a few people laughed about it. It was so awkward with how offensive he took the joke.
GroseJoy2theWorld 8y ago My newest boss at the time had accidentally brushed my butt with her hand and said sorry I didn't mean to. I didn't have my work-filter on so I naturally teased her a little with a wink and a sure. She got really flustered and uncomfortable. I don't think it had anything to do with me but a week later she quit.
mallardman57 8y ago It was early in the season and my coach didn't really know everyone's name and background. Us kids knew each other pretty well, however. We began practice and he noticed our motivation was low and we kinda moped through the drills even the fun ones. Half way through practice he finally said, come on guys what's wrong? You all look like your mothers just died. Well turns out a week ago ones of our teammate's mother had died of cancer leaving her devastated family behind. So yeah, that was pretty awkward.
. 8y ago When we were young kids whenever we asked my mom what was cooking for dinner she'd reply your underwear lol. So one day my stepdad is standing in the doorway, distracted by something on tv, and my sister asks what smells so good? And he quickly replies your underwear trying to be funny. Не still hasn't lived that one down.
drivingriley 8y ago This happened to me yesterday. My younger cousin had spent the majority of our beach vacation playing video games in the game room of the house we rented. The house was enormous and it was easy to get turned around with several floors and bedrooms we had about 20 people staying in the house. After several days of pestering him to come out and enjoy the beach/family I had it in my mind to open up the game room door quickly and yell boo! Well...I did...and it wasn't the game room. It was my mom's friend struggling
8y ago We were at a church wedding where the minister felt the need to tell what he thought was an amusing story during his sermon. Не talked about a wedding where everyone else was ready to go except for the groom, who didn't show up. Turns out that he was found on the course with his one true love: golf! The bride was furious and interrupted his sermon to say that she felt his so-called humor was inappropriate and to please get on with the ceremony.
Fatcatattack94 8y ago I was at a suicide awareness function where there was a local band playing music. The lead singer almost dropped his guitar and said.. oh my guitar just tried to commit suicide.. yeah..... not many people laughed.......
cervo07 . 8y ago Guy at school told me a ya mumma joke. | told him my mum was dead. My mum was not dead. It was an hilarious joke. The guy thought I was for real, told his mum and that evening his mum calls my house to offer condolences. My mum answers.
Sad_Panda_22 8y ago Didn't witness it-l caused it. Walked out of middle school one day and over to two friends who were waiting for the buses to arrive. They both were standing there not talking, which was odd for the two usually overtalkative teenage girls. Me, trying to lighten up the mood, asked, Jeeze, who died? Turns out the one girl's grandfather had passed away. The look on both of their faces as soon as the words left my mouth will forever be seared into my brain.
titanruler77 . 8y ago Pronounced cake in a weird way meaning to be harmless in class (very bored) and said cock really loudly
biggiefoxie . 8y ago Told on a different thread. | had a friend who'd been kidnapped and tortured by an ex boyfriend. He'd sliced up her arms, legs and stomach pretty bad. But she'd gotten over it for the most part, as much as one would expect. Still, when I jokingly yelled BITCH I WILL CUT YOU at her at a party... She was not amused. | immediately realized what I'd done and apologized profusely.
godmodedio 8y ago My friend (before we were properly friends) looked rather down at a party. Naturally | told her she looked like her dog had died. Turns out it did.
saintraywood . 8y ago I met a German guy who said he was raised in Lancaster. I joked, You know, you've got the handsome looks of a German. You have a jaw like a Nazi propaganda poster. Karl was not amused... nor were his friends
AsaEx . 8y ago A few days ago my boss told me I could go home early because we were slow that day. I said something along the lines of okay, as long as this didn't happen again. The next day he calls a meeting and everyone's hours are cut back.
Paula-Abdul-Jabbar . 8y ago I worked McDonald's drive-thru back in high school. Had that Let Me Love You song stuck in my head, when a customer pulled up. I answered the headset by saying Welcome to McDonald's, how may I love you?
nolliefakie 8y ago One time I was at dinner with my family and my cousin, we were all having a good talk about television shows. My dad brought up the show Pawn Stars and we had a good chat about the show and how the acting is all fake. So my cousin decided to bring up another show. Не accidentally slurred his words and this is his exact sentence you think Pawn Stars is bad, have you ever watched hardcore porn?!... pawn , hardcore pawn, I mean pawn. Was awkward but we all just kinda pretended we didn't hear it
SidewaysGinger 8y ago I witnessed this situation because it I did it. One of the first times I met my wife's parents before we were even dating they were telling her about a tumor her aunt was diagnosed with and I blurt out It's not a toomah in my best Arnold voice. My family would have laughed. Her family just stared at me like what the fuck is wrong with you.
photonrain 8y ago Years ago when I was about 18 a female friend and I are driving around town in a car and see a hitcher so pick him up. Almost immediately he says who wants to hear a joke about an abortion? Dead silence, her and I had just finished talking about her guilt from recent abortion. It is pretty obvious what has happened and the hitcher feels bad. Не says Geez, sorry, it is like when you make a joke about someones mom and they're dead. Dead silence. Both her parents died a couple of years early. Can
Jammertal17 . 8y ago I was running a 3k during track in high school. This one guy passed me, and I said good job. Не didn't respond. It seemed like he had wireless earbuds in, so I said something to the effect of, if you can hear me. I realize after the race that they were hearing aids and I felt like an ass :/
everythingispiders . 8y ago Years ago I made a your mom joke to a friend I hadn't known for very long. Yup, her response was my mom is dead.
+ 8y ago I was at a wedding and a guy at my table was bald and had no eye brows. Having competed in swim competitions I thought that maybe he was a hardcore swimmer and asked him joively if that's why he shaved his eye brows. Не had cancer. Open mouth, insert foot.
JulienBrightside . 8y ago It-support work colleague was on the phone with someone and the computer was taking its time. She asked him to tell her a joke to pass the time. Не went with a dead baby joke. She was Head Doc of the Maternity ward. She didn't find it funny.
8y ago I went up to the head chef at the restaurant I part-time at like yo that new waitress has a fat ol ass. Не said what's that? And I got weird. So I said who's the new waitress? And he said my daughters godmother. :|
. 8y ago I proclaimed Nation wide is on your side when I thought it was relevant. Nobody laughed. Or commented. We just moved on.
62Lego_Bricks . 8y ago When I was younger I used to use that you're adopted and your parents don't even love you from Dodgeball as a joke argument. Went to my best friend's large family event, said it to one of his cousins, she was adopted. Oh god that was a shitty awkward feeling for 10 yr old me
mostheadliest 8y ago When I was 16 I got into a head on collision with a school acquaintances dad. I was completely at fault. For years after that our running joke was that I was trying to kill his dad. I ran into him at a bar after years of not seeing him and joked tell your dad to watch his back. He's a dead man when I see him! Turns out he had attended his dad's funeral earlier that day.
OctoSash 8y ago I've only tried to use yo mama jokingly twice in my entire life. Both times, the person's mother had died unbeknownst to me.

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