20 Dudes Whose Attempts With Women Will Make You Cringe Until You’re Sad

When it comes to dating in the digital age, it’s not uncommon for women to receive unsolicited, cringeworthy messages from men.

From cheesy pick-up lines to overly aggressive advances, these messages can make the dating experience feel overwhelming and frustrating. But why do some guys think these tactics will actually work?

Whether you’re a woman who’s tired of receiving unwanted messages or a man who wants to improve your dating game, these screenshots will provide some valuable insight on what (not) to do. Or, it will just make you cringe until you’re sad.


1. “Nice Guys Finish Last”

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2. “Am I The Nice Guy For Staring Down A Guy Talking To My Crush?”

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3. “Saw This On Twitter The Other Day And Thought It Fit—nice Guy Expects To ‘Netflix And Chill’ After Helping Woman Get A Job He Recommended”

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4. “B-But, M’lady, I Thought We Were… Friends?”

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5. “A Woman In My Neighborhood Was Followed By A Man While She Was Jogging And Posted A Safety Warning To Let Others Know. This Guy Pops Up In The Chat”

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6. “I Thought You Were A Good Person”

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7. “Sometimes I Read Stuff Like This And Pray Those People Are Joking”

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8. “I Felt This In My Soul”

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9. “Guy Thinks A Girl Was Begging For Sex When She Was Nice To Him At Lunch”

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10. “Now That’s Some Sadcringe”

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11. “Found On Twitter”

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12. “Even The Wings Were Bad This Time”

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13. “Homie Just Kept Going”

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14. “Redditor Gets A Job To Try To Get Laid With Coworkers”

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15. “Poor Guy”

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16. “O-O Okay Then”

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17. “He’s Just A Nice Guy, Megan”

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18. “Yikes”

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19. “What???”

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20. “Well That’s Not Creepy”

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h/t

Nate Armbruster

Nate Armbruster is a stand-up comedian and writer based in Chicago who is likely writing a joke as you read this. Find him online at natecomedy.com.