14 Dark Humor Jokes About Dating

14 Taylor Tomlinson’s Self-Fulfilling Prophecy

Tomlinson has had trouble trusting her dates ever since one of her partners cheated on her multiple times in college. After speaking with her therapist though, she made a discovery about herself that might explain things (possible witchcraft aside).

13 Sam Morril Is a Boyfriend/Therapist

“I was talking to my therapist and he goes, ‘You tend to pursue damaged people and try to help them.’ I was like, ‘You too.’”

12 Robot Chicken’s Video Dating

Finding someone is hard, especially if you’re looking through videos of would-be partners. It gets especially weird if the dating video is from The Ring.

11 Jen Kirkman’s Horniness After Divorce

After she separated from her husband, Kirkman went into detail about the two dates she went on immediately afterward. The amount of horniness she felt took her to some sad places.

10 ‘Saturday Night Live’ Presents Her to You

Getting set up by a person’s parents is awkward enough but having all of your date’s potential flaws expressed through a song is a nightmare.

9 Aparna Narcherla Picks Her Date Spots

“I try to pick a bar where if I go missing, people will be like, ‘At least she had a good time before she left.’ At least four stars.”

8 ‘The Simpsons’ Dating Auction

A charity auction of Springfield’s most eligible existing bachelors goes about as well as expected.

7 Carly Aquilino is Done

6 Iliza Shlesinger Has Advice for Young Men

As an “elder Millennial” that’s married with kids, Shlesinger has some advice for young guys trying to initiate sex. Mostly just don’t make it seem like you’re holding a woman hostage while you’re naked.

5 Donald Glover Knows Why There Are No ‘Crazy Man Stories’

“I realized every man in this room has a crazy woman story. Why don’t women have crazy men stories? I don’t really hear them. Then I realized, oh, if you have a crazy boyfriend, you’re gonna die.”

4 Nicole Byer on Tinder

“I matched with this guy named Nick. His first message to me was ‘Puerto Rican, Black, or Mexican, let’s talk about it.’ So I said, ‘Are you asking what I am? I’m real Black.’ He said, ‘That was my inference, could have gone either way though.’ I said, ‘Cool, what are you — white, white trash, privileged white or rapey white?’”

*Audience applauds*

“Thank you for clapping. I also clapped alone in my room when I wrote it.”

3 Emily Heller Wants to Be Single Forever

“I just really like to say I want to be single forever in front of my married friends because they hate that. There’s always one that will condescend to me about it and be like, ‘Come on, single forever? You don’t know that. You can’t know you’re gonna want something forever.’ And I’m like, ‘That is an amazing point. That would be stupid of me to know I want something forever in my 20s. The only thing I can think of that might be stupider would be spending $50,000 to say it in front of everyone I know.’”

2 ‘Family Guy’s 37-Year-Old Woman on a Blind Date

1 Key and Peele’s First Date

One way to judge a date is seeing how they treat waiters and service staff. Key & Peele displays how bad it can really get and how ominous it could be.