Found on r/AskReddit. Thanks to those who gave permission to use their comments!
1. “I have to call my mum, she asked me to call her after I got my first impression of you.” – XyzzyPop
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2. “My ex is over there, quick, act like we’re interested in each other!” – eternityinspace
3. So are we gonna fuck? Cuz I got a WoW raid later – pull_my_finger_AGAIN
4. I masturbate to your Facebook photos. – r_antrobus
5. Hope you don’t mind if my mother joins us. – RichWPX
6. Nothing. Don’t say anything. – ipconfider
7. “I think your skin will do nicely.” – wesmaster45

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8. I went on a first date with a girl to an Italian restaurant. On the drive over, there were a few Mexican workers standing on the side of the street. We get to the restaurant and all she wants to talk about are those Mexicans and how much she hates Mexicans. Well, I don’t know how well she looked at me, but I am Mexican. – TheProphecyIsNigh
10. I was once on a date with a guy, we were on his rooftop drinking wine and he looks around and turns to me and says, “Ya know, I could totally rape you on this roof if I wanted to.” – jedi_slut
11. “Yes, those are my parents at the next table. Great people. We go everywhere together.” – partial_to_dreamers
12. “We need to leave – my ex just walked in and technically I’m not allowed within 200 feet.” – MrBillyLotion
13. “I don’t know how I feel about abortions. Don’t get me wrong, I love the idea of killing unwanted babies, it’s just the idea of letting women make a decision that doesn’t sit well with me.” – MrCleanMagicReach
14. “Pleased to meet you, with meat to please you.” – TheAgreeableCow
15. “I love you.” – yours_duly
16. “I wonder if you’re as tight as your mom is.” – Hellaman
17. “I don’t think that was just a fart.” – PragmaticWetBlanket
18. Well, seeing as this recently happened to me I’ve got an answer. So I asked her out and she said yes quite enthusiastically. The first thing, the first words that come out of her mouth are “I’m not looking for a relationship.” Definitely killed the mood. – Tjler
19. “Wow, are you going to wear that? It makes you look really fat.” – somnodoc
20. “I knew I should’ve worn my other fedora.” – gabriot
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21. “Are you from Ireland? Because my cock is Dublin.” – Circleclicker