15 Terrible Ways To Ask Someone Out, According To The People Who Were Asked

List Rules
Vote up the worst ways to ask someone out that would end in rejection.

Dating can be pretty chaotic. But before you even get to that first date, you have to get past the difficult part: asking someone out. These Redditors have kindly shared the worst ways to ask someone out so you don't repeat their awkward stories. If you're looking to avoid rejection, then keep reading to learn how not to ask someone out.


  • 1
    44 VOTES

    "You Wouldn't Date A Man Like Me... Right?"

    From Redditor u/Cheshire0226:

    I was in my early 20’s working in retail at a customer service desk. I was helping a customer when the sales manager randomly comes up to look over my shoulder to see what I’m doing. I just ignore him and he tries to jump into my conversation with the customer. I don’t remember exactly how it came up, but right in front of the customer he said “you wouldn’t date a man like me”. I was floored. I quickly finished with my customer and then confronted him in the managers bridge. Btw, he was married and I was living with my boyfriend. I told him that if he was unhappy in his marriage he needed to deal with that before hitting on other women. He said he wasn’t unhappy and his wife didn’t need to know. Yeah, I should have reported his creepy *ss after that.

  • 2
    39 VOTES

    "We Just Met In A Foreign Country. Want To Come On A Remote Hike?"

    From Redditor u/itselevenoclock:

    I had just moved to Spain from the US two weeks before, didn't know anyone. Found an English-used bookshop, and was perusing the shelves when another American walks in. He starts chatting with me and literally fist bumps me 10 times in our 3-minute conversation. Says we should hang out sometime, and I say sure thinking this is a "we're both American and don't know anyone in this country" type thing. When someone fist bumps me, I assume we are in "bro"/friendly territory.

    Turns out he wanted to go on a date, which I didn't realize until he asked me out 3 nights in a row. Unfortunately for him, I didn't have wifi in my apartment yet so I only checked my phone for 30 minutes a day when I stopped in a cafe for wifi. Then he got mad when I wouldn't travel with him to a remote park over an hour away from my apartment. We did not go on a date.

  • 3
    34 VOTES

    "I Couldn't Decide If I Like You Or Your Friend, But You're Single So..."

    From Redditor u/himynameisbetty:

    “I couldn’t decide if I liked you or your friend more, because you were always together. But I finally figured out I like you, and not just because you’re single. Will you be my girlfriend?”

  • 4
    33 VOTES

    "I Heard Your Sister Passed. Want To Get A Drink?"

    From Redditor u/oldpeoplelovebeige:

    My sibling passed and a guy I knew found out about it, he took a shirtless photo on Snapchat and captioned something along the lines of “I’m sorry to hear your sister passed, come over for some drinks and we can talk about it if you want.”

    I got him to come over with the liquor and kicked him out immediately after he put the drinks in the fridge.

  • 5
    33 VOTES

    "If You Don't Want To Date Me, Can I At Least Sell You Something?"

    From Redditor u/Princessneon:

    A man stepped in front of me as I ran to catch the trolley I took home from work and asked for my number. When I said no he tried to sell me weed.

  • 6
    27 VOTES

    "Surprise! This Is Actually A Date!"

    From Redditor u/bovienj:

    "Wanna go to a movie as friends?"

    At the movie theatre: "Guess what?! It's actually a date! Hahahaha!"