• 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.
