• From corny pick-up lines to asking about boners, the Planet Dolan crew re-enact some
of the best true stories from our subreddit about the dumbest ways we ever tried to start
a conversation. I’m Pringle and today I’ll be your narrator.
Number 10 was submitted by BakaNekoSassou03 Doopie
Doopie has never been good at being sociable but, when she was younger, it was horrible.
She would say things that "normal people" would be ashamed to say. One time when she
was 7, Doopie was at school and wanted to talk with someone. So, she went to a girl
in her class and said, “Hey! Guess whose panties I’m wearing right now.” She said,
“Well, yours?” Doopie said, “No, my mom’s panties!” It was true because all
of her panties were in the washing machine, so she had to borrow some from her mom. Doopie
was so ashamed she said that, even though she was really young.
Number 9 was submitted by EnclaveSergeant Sweetcommando
The dumbest way Sweetcommando ever tried starting a conversation was when he was coming home
from the Marine Corps on a passenger plane. He sat next to a lady during the flight and
decided to strike up a conversation. He said, “I killed a guy in Iraq.” She turned and
looked at him, scared and confused. Then Sweetcommando said, “What? You’re acting like you’ve
just seen a ghost.” The lady replied, “No. It was what you said about killing a guy.”
Lucky for him, the plane was about to land in the United States. As he left the airport,
the lady looked so shocked and scared from what Sweetcommando said that he just walked
away, got in his car, and went home.
Number 8 was submitted by NorahPines Andiemations When she was 12, Andie would ride a really
crowded bus to and from school. She always sat with her two best friends so she wouldn’t
have to sit with a random person. However, her friends were in band and she wasn't. That
meant that sometimes Andie would have to sit with her sister while her friends went to
their band concert. One day, her sister got sick, and it happened to be the day that her
two friends had a band concert. For the first time in her life, Andie had to ride the bus
with someone random. Of course, the cutest boy in the entire 7th grade chose to sit next
to her, and that just made her even more awkward and sweaty than she already was. About five
minutes into the bus ride, she decided to try and start up a conversation. So she cleared
her mind, took a deep breath, and shouted at the top of her lungs, “Hi! I’m Andie!
I’m 12 and own a floofy poofy cat! Wanna get married!” The whole bus stared at her
like she was insane, and the boy next to her started listening to his music on the loudest
setting to calm himself down. She never saw him again, and never told anyone about what
happened.
Number 7 was submitted by NovuAkainu Danger Dolan
When he was 14, Dolan and his family went on a trip across the United States, and one
of their stops was in Oregon. They decided to camp for the night when his mother asked
him and his brother, Zaraganba, to get some wood for a fire. They did, but all in a slightly
uncomfortable silence. Dolan felt like striking up a conversation, but had trouble deciding
on what to talk about. He suddenly asked, “Do you plan on having sex with your girlfriend
when we go home?” Zaraganba immediately stopped collecting wood and said, “We're
not talking about this, and if you ever do again, I'll punch you in the jaw.” He then
resumed picking up wood. For the rest of the night, Dolan and Zaraganba sat in an even
more uncomfortable silence. They didn’t speak to each other until the next day.
Number 6 was submitted by RadiantNarwhal SaltySquid So there was this one girl who SaltySquid
thought would be super fun to spark a friendship with, and was super nervous about starting
a conversation with her. One day, he found her standing alone so he went up to her. In
a dead-serious voice, he said, “I know why you’re not hot. It’s because I’m your
biggest fan.” She just walked away and didn't speak to him for a few days. Later, they started
talking again and now they’re best friends.
Number 5 was submitted by Mote-of-Lobross Tolop
Back when Tolop was in his Goth phase, girls would come up to him without him having to
make any effort. When he outgrew the whole Goth thing, that stopped happening and he
actually had to approach girls himself. Since he was so out of practice, Tolop always ended
up being an awkward goofball. One time when he was at a friend’s party, he ran into
a girl, Spincess, who was playing Final Fantasy III on the host's Super Nintendo. She was
fighting a boss called Ultros, who is a giant purple octopus. Tolop went up to her and said,
“Ah, getting tentacled by Ultros, I see...” Spincess replied, “Um… yeah…” and
just stared at Tolop for a second before he said, “Okay... I'll go over... um... there
now. Bye.”
Number 4 was submitted by syncjacket Spinalpalm Last June, Spinalpalm and a few friends went
to Denver Comic Con. On their third day there, they decided to try out a special event called,
"Sci-Fi Speed Dating." It was just a standard speed dating thing, but everyone was in costume.
One of his friends decided to try it because she was looking to get back into the dating
scene, but didn't know how to start a conversation. Spinalpalm told her to just be herself and
try not to say anything remotely stupid such as, "Do you like milk?" His friend laughed
and said she surely wouldn’t. Once it was his turn to start the Sci-Fi Speed Dating,
fourteen people were there. He then saw the most beautiful woman he had ever seen, PrincessProton.
Once the announcer launched the clock, Spinalpalm had to think of something fast to say. At
that point in time, he hadn’t been dating in a while. He panicked, with time starting
to run out. He just blurted out, “So.... do you like milk?” PrincessProton looked
at him in complete confusion for the remaining twenty seconds. He bowed his head in shame
until the end of the speed date.
Number 3 was submitted by ClearestDiamond Grgak
One time, Grgak wanted to talk to a person next to him in school. Unfortunately, Grgak
couldn't get his attention. So, he thought it would be a good idea to stomp his feet
while screaming, “Raisin bread makes my insides feel weird!” He also screamed, “Potato
bread is yellow because of the sunny sun!” And because he was indoors, his screams and
foot stomps echoed. It certainly got the other person’s attention. Maybe a little too well.
Number 2 was submitted by Jacobawesome74 Hellbent While Hellbent was scrolling through a particular
comedy app one day, he came across a certain comic. It was about a knight sent to slay
a dragon, but it turned out that . He was very confused, yet... ashamed when he looked
down and saw that he was aroused. Hellbent immediately went to a different app and asked
a friend if he ever saw something that gave him a confused boner. His friend was confused
and startled, especially when Hellbent showed him the thing in question. Since then, they
agreed to never speak of it again.
Number 1 – What was the dumbest way I ever tried to start
a conversation?
Huge thanks for the folks over on our Planet Dolan subreddit for submitting their stories.
We have another question for you: “What's the strangest secret you found out by accident?”
Let us know in the reddit page linked below and you might be featured in a future countdown