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All About Lily Chou-Chou:

  • Enjo Kosai: Hoshino eventually blackmails Tsuda into becoming this under his 'payroll'. Later she sees nothing wrong with her 'job' as it pays well. At one point she even stole her client's wallet.

Anime & Manga:

  • Hell Girl has a lot of these, at least in the beginning of the series. And they receive their comeuppance. Boy, do they ever.
    • The worst of them is Aya Kuroda from the anime's very first episode. She not only bullies her rival Mayumi Hashimoto, but she frames her for embezzlement, forces her into Compensated Dating to earn the money back, and blackmails her with photos of her "illegal/immoral behavior" Seeing her get Dragged Off to Hell is quite satisfying, even if Mayumi must also suffer the same fate when she dies.

Video Games:

  • In one of the Yandere Simulator videos, Musume Ronshaku throws slurs at Kokona for being engaged in Compensated Dating to earn money and help her father with his debt, despite being more of a slut than her and wearing a shorter school skirt. She also mocks Kokona for her large chest, despite not being particularly small-chested, either. In fact, she has the third largest chest (1.5) after Kokona and Mai Waifu (2) and Saki Miyu (1.7) out of all the currently implemented characters.

Yamada-kun and the Seven Witches

  • Cultural Translation: When rattling off rumors about what Yamada did in his first year that caused him to be suspended a second time, the chairperson mentions that one of the rumors was that he forced a girl into Compensated Dating. In the English translation, it is changed to Yamada threatening a girl into prostitution, probably because fewer Western readers would know what compensated dating is. The implication is also prostitution in the original Japanese edition, given that Shiraishi is shown in an Imagine Spot sitting half-naked on a bed while Yamada counts money.
    Unclear whether correct (10) 

Hell Teacher Nube:

  • Enjo Kosai:
    • Nube accuses Izuna of this. He's not far off.
    • And if she could get away with it, Miki would dive in headfirst. Then her sugar daddy turned out to be a god...

I Think We'll Be Okay:

  • Compensated Dating: After being demanded to pay debt to a loan shark, Kosuke becomes so desperate for money that she signs up to go on a compensated group date for 76,000 yen. (Almost $720 in US dollars.) Kosuke herself notes that while going on paid dates might not be bad in and of itself, she does acknowledge that pure and innocent dinner dates aren't what everyone thinks of when they think of compensated dating.

Majokko Tsukune-chan:

  • Enjo Kosai: When Mr. Mayor gives Tsukune her New Year’s money, Tony jokes “So that’s the going rate for enjo kosai these days?” Mr. Mayor protests that it's Not What It Looks Like.

Megatokyo

  • Enjo Kosai: Is seen engaging in this a couple times.
    Largo: What are the m4d skillz that make you who you are??? What are you good at?!?
    Junko: I AM GOOD AT TAKING ADVANTAGE OF OLDER MEN AND GETTING MONEY FROM THEM!!!

MSF High Forum

  • Attention everyone! She's here, she's nice, she's friendly...she's a rotten kind of cute, give it up, for the ZOMBIE ENJO KOSAI. Inspired by the song Zombie Prostitute, by Voltaire.

Narrative Structure:

School Days:

Sekirei:

  • Compensated Dating: Shown going on one with Takami, in order to make up for the time he took off to protect Kusano. !!!Sensual Phrase
  • Compensated Dating: Sakuya is a rare male example, and in fact this is how he got hooked up with Ayako in the past.

Yandere Simulator - Other Characters:

  • Bitch in Sheep's Clothing: The ones who were removed at any rate. While Yan-chan can gossip with nearly every NPC student, this group immediately claimed disgust upon hearing that test-rival Kokona engages in Compensated Dating, and would exile her to sit on the roof by herself. Even Saki, Kokona's best friend, stopped talking to her. These were the same girls Kokona made a snack for earlier in the week. While Mei, Yuna, and Koharu only acted this way if they found out about the Compensated Dating, Yui… was a different case.
    Non-Japanese use; seems misuse ( 4 entries) 

AKB48:

The Old Dark House (1932)

  • Compensated Dating: Gladys tells Roger that while Sir William pays her to hang out with him, Sir William "doesn't expect anything. You know what I mean by 'anything', don't you?"

Skip Beat!:

  • Enjo Kosai: Qin works by role playing Replacement Goldfish with men, so they could discourage a persistent ex-girlfriend and reconnect with a man's daughter.

The Sopranos S 6 E 18 Kennedy And Heidi:

  • Compensated Dating: Sonya got involved with Chris and Tony, among others, and also works as a stripper to put herself through college.
    Two correct sounding examples under different names of the trope ( 2 entries) 

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