• From trying to put gummies in a girl’s butt to offering to torture someone to prove
your love, the Planet Dolan crew re-enacts some more of the best, true stories from our
subreddit about the dumbest things they said when trying to be romantic – I’m Doopie
and today I’ll be your narrator.
10 – SaltOfTheSquid - Nixxiom Nixxiom was something of an awkward kid.
One day he got the courage to ask a girl out, and what do you know, it worked.
They started role-playing through text.
Sexy role-playing.
The conversation ended up getting all spicy.
So In his saucy state he thought of the most romantic thing he could say.
"I'll lick the nipples of your breast."
Somehow this didn’t deter her, neither did the time he tried to shove gummy bears in
her ass.
9 – tinypapercuts - Honeybits Honeybits was chatting with a guy in the hallway
and she was trying to be kinda flirty.
She was not good at flirting.
They both shared an interest in video games, and a Mario Kart tournament was coming up.
So she asked him if he was going to enter, he replied "I'm gonna wreck all of you at
Mario Kart!"
So of course she replied: "Oh yeah you can wreck me any day.”
She was immediately caught off guard by her own mouth and just ran off without saying
anything else.
8 – Iamisabel2000 - Shima Shima was eating mozzarella sticks at a pub
named Humperdinks with this one guy.
For some reason she said "Your stick will spray mozzarella after HUMPerdinking me" She
then bit off a piece of the mozzarella stick and cheese oozed out everywhere.
Pretty sexy, I know.
7 – LunaMoon37’s Boyfriend - Dolan Dolan was just sitting at lunch with his girl
when he suddenly said, "I wish you were a door so I could bang you all day".
She kinda looked at him and was like " what?".
Everyone was staring at him.
The dumb thing is she tried to make him feel better by saying "I'm wearing no socks and
have panties to match."
6 - Pemandala - mkylem So, one day mkylem went to his ex's house
to watch a movie.
The movie was about this crazy man who used to kill and torture people to prove his love
to a woman and she was like: "I don't know if it's creepy or romantic that someone could
actually do that for love.”
Being a rash person he immediately said: "I’d torture someone to prove my love to you"...
and he just saw her face and he knew that he just completely screwed up the moment.
5 - fallior - Emojie Emojie got 2 cool pairs of socks that he knew
his crush would like.
The plan was to put them on her feet, Cinderella-glass-slipper style.
But yeah, it was just awkward and after showing her the socks and offering to slip them on
her tootsies he immediately felt weird about it.
4 - lonelyduck235 - Andiemations Andiemations dumbest thing was probably when
she said "Hey I will put you in my hole."
She followed that up with: "I mean, something like, get your dick in my pussy" He told her
to leave and later blocked her on twitter and stuff.
She learned a lesson from that.
3 - Its-OverBaka - Pandora
Pandora’s began flirting with her and she needed to reply with something so she said:
“You're as pretty as a flower.”
He just stared back at her with a blank look, clearly trying to process what had just been
said.
He said something beautiful in return, so Pandora blurted out: "I CAN'T WAIT UNTIL YOU
MEET MY MOM!"
He ran away and slammed the door behind him.
2 - LeviathanOnEarth - Pringle When Pringle had a crush on his dance partner
from class and so of course he tried to flirt with her.
He thought for a long time of what to say and in his next class he ended up spewing
out: "I LIKE YOUR FACE ITS VERY SOFT AND SQUISHY!"
And it was pretty awkward for a long time after that.
Number one was submitted by me, what was the dumbest thing I’ve ever said while trying
to be romantic?
Huge thanks for the folks over on our Planet Dolan subreddit for submitting their stories.
We have another question for you: “What's the craziest thing you’ve ever seen your
boyfriend do?”
Let us know in the reddit page linked below and you might be featured
in a future countdown.