• From unnecessary pick-up line explanations to fumbling compliments, the Planet Dolan
crew re-enact some of the best true stories from our subreddit about the dumbest things
we’ve said when trying to be romantic.
I’m Hellbent and today I’ll be your narrator.
Number 10 was submitted by TheRealGTStryder Zaraganba
There was a girl Zaraganba liked when he was in 4th grade.
One day, he decided that he was going to tell her how he felt about her.
When he walked up to her, instead of asking, “Want to go on a road trip in an RV, then
maybe go somewhere alone,” he accidentally asked, “Want to ride on my big dick… and
go somewhere alone?”
They stood there in silence, but then started laughing their asses off when Zaraganba explained
what he meant to say.
They ended up going on that road trip.
Number 9 was submitted by Grimflintlock SaltySquid
SaltySquid and his girlfriend were being flirtatious.
She said something, and he tried to think of something to say in return.
Eventually, he mustered up the courage to say what was on his mind, which was, “I
gotta tell ya something crazy, so lube up that eyehole love, ‘cause I’m gonna fuck
your mind.
Er, I mean…!”
She gave him a confused look and said she didn’t understand.
SaltySquid said, “Goddamn it, I messed it all up!”
She laughed and said that she understood.
To this day, they continue to laugh about it, though it doesn’t make it any less embarrassing.
Number 8 was submitted by Ok_memes Tolop
Tolop was a shy kid growing up, and would sit by himself at lunch.
One day, out of nowhere, a girl, Spincess, sat down next to him and asked, “Is this
seat taken?”
Tolop started panicking, so being the shy and dumb kid he was, he tried to flirt by
saying something like the “Did you fall from heaven?”
line.
After fumbling around with it in his head, he ended up saying, “When flies get fruit
from hell.”
Spincess looked at him, dumbfounded.
She walked away and didn’t talk to him for a year, but two years later she became his
girlfriend.
Number 7 was submitted by punkie120 Spinalpalm
When he was in 6th grade, Spinalpalm had a crush on a girl, PrincessProton, who was in
his class.
At that time, he didn’t know what a lesbian was so he asked his big brother, who then
said, “you.”
The next day, Spinalpalm asked her out.
Instead of saying, “Do you want to go out with me,” he said, “Do you want to go
out with a lesbian?”
As he asked her, he pointed to himself.
Everyone laughed, but it ended up working out – she said ‘yes’ and they’ve been
together ever since.
Number 6 was submitted by KiwiCatMustKillWCute Cidius
In 4th grade, Cid had a crush on a girl.
One day, at recess, he handed her a drawing he did of her as a princess, which she thought
was very impressive.
He said nervously, “I think you’re the princess of this town.”
Then, he corrected himself by saying, “Even though this is a democratic country.
I guess you could be the President, but only boys can do that.”
Then, he covered his mouth and blushed.
He apologized, but his crush just laughed.
They ended up dating during fifth and sixth grade, but the relationship ended when she
had to move away.
Number 5 was submitted by Charlotte3128 Doopie
Doopie once had a crush on a boy for three years, and was always really shy when talking
with him.
She would fumble her words and end up saying something awkward.
The day before Christmas break, they were playing a 7th versus 8th grade volleyball
game.
While headed toward the stairwell after the game, Doopie saw that her crush was walking
behind her.
She decided to praise him on what a good job he did during the game.
Instead of saying, “Hey, you did pretty well in the volleyball game,” Doopie ended
up saying, “Hey, you, uh, fuck, you did good in the gay me!”
Trying to correct herself, she said, “Shit, that’s not what I meant.
I tried to say that you did game in the good, and have a nice time in breaking Christmas.”
A lot of people would joke that he was gay, too, so it was extremely awkward.
Number 4 was submitted by KatKAtSMAT MKyleM
When MKyleM was in 8th grade, he had a huge crush on a girl in his class.
Since it was nearing the end of the school year, he decided to confess his feelings for
her.
He tried to say, “I love you like bees love honey.”
Instead, what came out was, “I love you like strippers love money.”
His crush stood there, shocked.
Everyone in the cafeteria laughed while MKyleM just stood there.
He ran into the bathroom, with his friends following him.
After graduation, he found out that she had been dating a high schooler.
Number 3 was submitted by DRG_Lancer Pringle
Not too long ago, Pringle and his girlfriend were watching anime.
He felt like trying to be romantic, so seeing how they liked anime he tried to make a reference
from something out of Berserk.
Pringle leaned over to his girlfriend’s ear and said, “My love for you is like a
truck.
BERSERKER!”
They sat there for a bit in silence, since what he had just said sounded very dumb.
Then, Pringle had the fantastic idea to finish his line by saying, “Do you want to be making
out?
Fuck Berserker!”
She busted out laughing and called him stupid for thinking that would work.
Well, it just so happens that it DID work…
Number 2 was submitted by RainOnMars Melissa
When she was in 5th grade, Melissa fumbled a lot with her words.
One time, when she was chatting with her friends, her crush, Nixxiom, walked up to her and asked
if he could have her cheese stick.
Melissa mumbled, “Yeah, I love you too.
Er, I meant yeah, you can have my please frick… wait, no, no, no.
I meant, can you kiss my mouth…
mother frick!”
When Nixxiom asked what she had just said, Melissa mixed up her words even more and said,
“Yes, you can kiss my mouth hole!”
Her friends stared at her for the longest time, but Nixxiom sat down and kissed her.
It was the best screw up Melissa ever made.
Number 1 – What was the dumbest thing I’ve ever said while trying
to be romantic?