• From inappropriate sandwich innuendo,
to totally ruining a game of spin the bottle,
the Planet Dolan crew re-enact some of the
best true stories from our subreddit: the
dumbest things you’ve said while trying
to be romantic – I’m Danger Dolans Mysterious
Brother and today I’ll be your narrator
10 - Swally0322 Nixxiom
Nixxiom once went out on a date with a girl
his friend Hellbent hooked him up with and
he was really nervous because he didn't usually
go on many dates. During the meal she says
to him "I'm having a really nice time tonight"
and Nixxiom didn't know what to say, so he
thought back to when his friends were talking
about pickup lines and for some reason he
said "You know I feel like you work at subway
because I bet you could handle my footlong".
She got up, walked out, and he hasn’t seen
her since.
9 - why_am_im_so_bored Pandora
When Pandora was younger, she was really keen
on a guy at school. One day she said to him
"Hey babe I bet you know how to 'fix my computer'".
He did, and came over to her house and looked
at her computer. There was obviously nothing
wrong with it, and what she really meant was
"Hey babe come over to my house so we can
kiss". She then tried to kiss him and he literally
climbed out of her window and told her he
could never like her. In a panic, she replied:
"But we go together better than shit and piss!".
Unsurprisingly, he never talked to her again
after that.
8 - Pinapplepunch GhostToast
When GhostToast was in 5th grade he was nervously
sitting next to his girlfriend in a grass
field. In a moment of panic, he said to her
‘Do you uh.. want to eat grass? He then
proceeded to eat some grass from the ground.
She stared blankly at him and got up and walked
away. The next day he saw her in class and
was so embarrassed he nearly peed his pants.
7 - TheHappyHopper Dolan
When Dolan was younger he tried to ask out
this girl at school when suddenly Hellbent
came running down the hall and yelled, “DUDE
YOU HAVE A MASSIVE ERECTION SEE LOOK AT YOUR
CROTCH”, this led him to walk away, silently
embarrassed, with everyone (including the
girl) laughing.
6 - KFORS Melissa
Melissa was once on a date with a guy and
decided to play a bit of pokemon go while
they walked home. When they got to her front
door she invited him in for some cold water
as it was a hot summer night and they had
just walked a mile. She nervously blurted,
"So do you want to come inside, drink some
water, maybe let me get a Pikachu?" Get it?
(peek at you) He just kind of stared at her
and said "No, I'm good thanks" She was hoping
a bad pun would loosen the mood, but she was
wrong. At least she didn't say something about
“Sqwirtling”.
5 - EveTheCursedGirl Snewpee and Doopie
Snewpee was attempting to be romantic with
her friend Doopie, giving her subtle hints
that she had a crush on her. But Doopie thought
she was joking around. Weeks later at a party,
Doopie showed up in a red dress and Snewpee
was in a tuxedo. She had brought Doopie flowers,
kneeled down on one knee and asked her to
be her girlfriend. She laughed, took the flowers,
and said 'You’re so sweet but I’m seeing
someone else.' She was shut down in front
of everyone. Doopie got off her knee, went
back home and cried as she ate the box of
chocolates she was supposed to give to her.
4 - InvisibleGuardian369 Slapped Ham
On the last day of school holidays, Slapped
Ham found a pretty flower that he wanted to
give to his crush on the first day of school.
He practiced what he was going to say to her:
"7 billion smiles and yours is my favorite"
then hand her the flower. But when he saw
her the next day he ran up to her really excited
saying "TAKE THE THING! TAKE IT!" She laughed
and when he explained what he had planned
she smiled and told him that it was beautiful
and what he actually said was funny and adorable.
3 - BluetheWartortle Pringle
When Pringle was a kid, he had a crush on
a girl in his class. One day, his friend Sweet
Commando told him to flirt with her so he
could win her heart. As Pringle walked over
to his crush he exclaimed: "Hey girl, you
look majestic like a horse." Apparently he
said that because he thought horses were the
most majestic animal in the world. She replied,
"Did you just say my face looks like a horse?"
After that, he froze in awkwardness, regretting
his decision immediately.
2 - SovereignofSabers Hellbent
When Hellbent was a kid, a girl wanted to
play spin the bottle with him. He didn’t
like her that much, but for some reason he
decided to tag along. She told him that they
were playing "super" spin the bottle, meaning
that each person had to say something romantic
when the bottle landed on them, and then kiss.
She spun it and it landed on Hellbent. He
didn't even know what "romantic" meant, but
she got up close to him and whispered, "What
do you think about me?" Without thinking,
he blurted out, "your head looks like a turnip,
and you smell like puberty-obesity." She looked
like she wanted to cry, but for some reason
she still kissed him on the cheek. He told
her that her lips were drier than lizard lips
and she ran out of the bathroom crying.
Number 1 – What’s something dumb you’ve
said while trying to be romantic?
I had my first girlfriend when I was about
10 or 11. It was weird, and I didn’t know
what I was doing. I must have liked her though
because one day I found a ring and I planned
on giving it to her as a present. We went
on a field trip to the local pool and I didn’t
talk to her much because I wanted to talk
without anyone else there. So, while we lined
up for the bus back to school, she wanted
to know if I still loved her, which she communicated
by passing messages through like 5 of her
friends. I said yes but they weren’t convinced.
After being pestered by them for AGES, I just
said no because it’s private and I really
hated talking to her friends about it. And
that’s how I accidentally dumped my first
girlfriend.
Huge thanks for the folks over on our Planet
Dolan subreddit for submitting their stories.
We have another question for you: “What’s
the weirdest conversation you’ve had with
a stranger?” Let us know in the reddit page
linked below and you might be featured in
a future countdown
