Chapter summaries Not Funny Jena Friedman

Sex Pays: Chapter Summary, Themes, and Key Takeaways

⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.

Summary

In this chapter, Jena Friedman explains that early in her comedy career, before she had any real credentials, she took a job as a sex columnist for a men’s fitness magazine. Her only qualification was that the job paid, and she describes the role as her first attempt to both inform and lightly troll male readers. The chapter is structured as a series of reader questions followed by her answers, with her commentary weaving in observations about gender, power, and the absurdity of dating advice.

The first question comes from a man who sees the same woman on the bus every morning and has started altering his commute to run into her. He wants to know how to approach her without seeming like a stalker. Friedman jokes that if he is a stalker, he should keep doing what he’s doing, but for everyone else, she suggests a simple greeting and paying attention to body language. She then spins out a hypothetical where the woman works at Planned Parenthood, and she encourages the reader to make a donation and ask for her number.

Next, a reader asks what the sexiest things are to say to a woman during sex. Friedman advises that context matters, warning against vulgar language unless the woman initiates it, and she jokes that the word “shlong” is a turn-off because it signals too much porn consumption. She suggests starting with something like “you’re beautiful,” though she admits the line gives her “cheese chills.” She then offers a darkly comic alternative about an ex who died in a fire, noting that women are supposedly suckers for ghost stories. She also jokes about scaring a girlfriend with a ski mask, though she later notes in a footnote that this bit was cut.

A friend of a reader reportedly receives a blow job every morning from his girlfriend so he won’t cheat. The reader thinks this is a great idea and asks how to bring it up with his own girlfriend. Friedman responds sharply, saying that healthy relationships shouldn’t involve coercion or manipulation, and she criticizes the friend for trying to manipulate his partner.

A reader who has been canceled on twice—once for work and once because her dad was sick—asks whether he should keep pursuing her. Friedman says it sounds like she’s not interested, but she allows for the possibility that the woman has a demanding job or a genuinely sick father. She advises sending one more short text that expresses how he feels, then leaving it alone if there’s no response. She also notes that worrying about seeming desperate is itself a form of desperation.

A reader asks whether he should accept a Facebook friend request from his ex. Friedman jokes that the ex must have recently gotten divorced and is looking to have sex with old flames without increasing her partner count, which she ties to cultural shaming of women. She then pivots to the real question: why is he still on Facebook?

A man worries that his girlfriend is still friends with an old boyfriend and sees him for dinner. Friedman tells him to worry about everything except this, because even if the girlfriend had feelings for her ex, there’s nothing he could do about it. She suggests the girlfriend probably enjoys the dinners because she was never in love with the ex in the first place, and she warns against controlling behavior.

A reader who used to be successful with women is now striking out and wants to know what he’s doing wrong. Friedman suggests he may have lost his mojo, possibly due to a job loss or an increased awareness of his own mediocrity. She recommends dating a different type of woman, meeting women in unusual places, or even trying men, whom she jokes will fuck anything.

The most serious question involves a man who had sex with a stripper at his own bachelor party and is getting married in a few days. He feels guilty and doesn’t know whether to tell his fiancée. Friedman says the scenario sucks all around, and she advises that if he wants a fun wedding, he should keep quiet and never do it again. If he wants a strong, honest marriage, he should come clean. She then spins out a dark hypothetical where the wedding is called off, he contracts a disease, the stripper ends up pregnant, and he’s left raising a son named Iggy alone, eventually finding peace in fatherhood.

A reader says his girlfriend is great in bed and a great person, but he can’t see himself marrying her. Friedman mocks the idea of a “romantic level,” suggesting that if he needs socially constructed gestures like rose petals, he should break it off for her sake.

A reader asks whether it’s okay to watch porn when his girlfriend said she was fine with it but then got upset when he admitted to masturbating to it. Friedman says every woman is different, but that it’s his body and his choice, and she suggests the real issue is his need for approval.

Other questions cover flavored condoms (she says no), oral sex that involves gagging and tears (she suggests asking if the person is comfortable), and whether to be honest about sexual history (she advises never being honest, and instead saying no one has counted until her).

A reader loves morning sex but his girlfriend doesn’t, and she sometimes gives in as a “mercy fuck.” Friedman is blunt: never coerce women into sexual activity, and if she’s not awake and consenting, it’s not morning sex, it’s assault. She suggests working harder to get her in the mood, or becoming nocturnal to match her schedule.

A reader isn’t into period sex, and Friedman tells him to get into it, calling it an age-old ritual that increases relationship satisfaction and longevity, with a dark joke about faking a murder-suicide.

A reader wants to try a threesome with two women and asks how to bring it up. Friedman admits she’s never had one, but she suggests ground rules: make sure the third person is consenting and legal, and make sure she’s pro-choice in case a condom breaks. She also questions why he assumes he’s enough for his girlfriend, suggesting the fantasy might be hers.

A reader accidentally shared intimate details about his girlfriend with a friend, and it got back to her. Friedman asks what he told, jokes about queefing, but then says that if it was serious, he betrayed her trust and that’s hard to come back from. She suggests buying roses, hiring a mariachi band, or taking her on a tropical vacation on Election Day so she doesn’t vote.

A reader wants to buy his girlfriend sexy underwear. Friedman says it’s a potential minefield, joking about wrong sizes and obscure STDs, and she suggests considering her tastes. She notes that she doesn’t wear lingerie because it’s an uncomfortable relic of patriarchal oppression, and she suggests an Amazon gift card instead.

A reader’s girlfriend is so loud during sex that the neighbors left a note. Friedman congratulates him for oversharing, then suggests telling her to keep it down, moving somewhere remote, or muffling her with a pillow without suffocating her.

A reader struggles with sex against a wall, which he sees in movies. Friedman explains that Hollywood is an illusion, that there’s probably a chair or a PA involved, and that most real women aren’t ninety pounds. She suggests weight training or hiring someone stronger.

A reader asks how to flirt without seeming aggressive. Friedman says women respond to appearance first, and humor works if you’re not attractive, unless she’s also a comedian. She jokes about telling a woman she looks under twenty-one and asking for her ID to find out if she’s an organ donor.

A reader wants to spice up his sex life with a hotel room. Friedman says it’s not sleazy, but she suggests a motel with bedbugs and gas station prosecco. She then applauds him for making an effort, and jokes about stealing a car and fleeing to Tijuana.

A reader thinks his girlfriend is reading his texts and emails. Friedman says it sounds like he doesn’t trust her, and she suggests a fun test: text a friend something specific about his girlfriend, like a cookie recipe or a pinky-up-the-butt reference, and see if she responds.

The final question comes from a man who ran into an old girlfriend and wants to rekindle the relationship. Friedman responds as if the letter is from Kevin, a real ex of hers. She thanks him for admitting he was wrong, says she looks great, and tells him she’s in a healthier relationship with herself. She jokes that she might acquiesce out of boredom or because he was the only guy who let her peg him, but she warns that she would remind him every day that she doesn’t need him. She ends by asking if he can pick up her mom from the airport.

Key Events

  • Friedman reveals she worked as a sex columnist for a men’s fitness magazine with no qualifications, purely for the pay.

  • She answers a series of reader questions on topics ranging from approaching a crush on the bus to whether to tell a fiancée about a bachelor-party infidelity.

  • She uses the bachelor-party question to spin out a dark hypothetical about a future son named Iggy, which becomes a recurring character in her imagination.

  • The final question triggers a personal response, as Friedman addresses the letter to “Kevin,” a real ex, and uses the platform to process her own feelings about the breakup.

  • She repeatedly emphasizes consent, warning against coercion in sexual situations, including morning sex and daily blow jobs.

Character Development

  • Jena Friedman: This chapter shows Friedman in an early-career role where she is still figuring out her voice. She is pragmatic about taking the job for money, but she uses the platform to push back against toxic masculinity and to advocate for consent. Her responses are a mix of genuine advice, absurdist humor, and social commentary. The final letter to Kevin reveals a more personal side, showing that her comedy is often rooted in real experiences and that she uses humor to process pain.

  • Kevin: Though he never appears directly, Kevin is the ex-boyfriend addressed in the final question. Friedman’s response paints him as apathetic and dismissive, and she credits his rejection with helping her discover inner strength. He functions as a symbol of the relationships she has left behind.

  • Iggy: Iggy is the fictional son in Friedman’s hypothetical about the bachelor-party infidelity. He represents the unexpected consequences of a single bad decision, and in the hypothetical, he becomes the source of meaning and peace in the man’s life.

Themes, Symbols, or Motifs

  • Consent and coercion: Friedman repeatedly returns to the importance of consent. She criticizes the friend who receives daily blow jobs as a form of manipulation, and she is blunt that morning sex without an awake and willing partner is assault.

  • Economics of comedy: The chapter opens with Friedman explaining that she took the job because it paid, and she jokes about being paid per word. This frames her comedy as a survival strategy, not just an artistic pursuit.

  • Gender double standards: Friedman points out that women are shamed for having multiple sexual partners, while men are not. She also critiques the idea that women need to be “romantic” in socially constructed ways.

  • Humor as social commentary: Friedman uses absurd hypotheticals—like the Planned Parenthood donation, the ski mask prank, and the Tijuana prison escape—to make serious points about dating, consent, and gender dynamics.

  • Hollywood vs. reality in sex: She contrasts movie sex, like sex against a wall, with the physical reality, noting that Hollywood is an illusion and that most women aren’t ninety pounds.

  • Relationship trust and betrayal: The questions about sharing intimate details, reading texts, and the bachelor-party infidelity all circle around trust and the consequences of betrayal.

  • Honesty vs. deception: Friedman gives contradictory advice on honesty, telling the bachelor-party groom to lie if he wants a fun wedding, but also telling the man with a sexual history to never be honest. This reflects the messy reality of relationships.

Why This Chapter Matters

This chapter is significant because it shows Friedman’s early development as a comedic voice. She is not yet the political satirist she would become, but she is already using humor to challenge gender norms and to advocate for consent. The chapter also reveals her willingness to be personal, as seen in the final letter to Kevin, which suggests that her comedy is often autobiographical. The structure of the Q&A format allows her to experiment with different tones, from absurdist to sincere, and it demonstrates her ability to find comedy in uncomfortable situations.

Study Questions and Answers

1. How does Friedman use the Q&A format to deliver social commentary?

Friedman uses the format to respond to real questions with a mix of genuine advice and absurd hypotheticals. For example, she answers the question about approaching a woman on the bus by spinning out a scenario involving a Planned Parenthood donation, which allows her to comment on reproductive rights while still addressing the reader’s concern. Similarly, she uses the bachelor-party question to imagine a worst-case scenario that touches on disease, single parenthood, and social safety nets. The format lets her be both helpful and subversive, and it allows her to critique gender norms without being preachy.

2. What is the role of consent in this chapter, and how does Friedman address it?

Consent is a recurring theme. Friedman is critical of the friend who receives daily blow jobs, calling it coercion and manipulation. She is even more direct about morning sex, stating that if a woman is not awake and consenting, it’s not morning sex, it’s assault. She also advises the man whose girlfriend is gagging during oral sex to ask if she’s comfortable. Her approach is to use humor to make the point memorable, but she is unambiguous about the underlying principle.

3. How does the final letter to Kevin reveal a more personal side of Friedman?

The final question, about rekindling a relationship with an ex, triggers a response that is clearly personal. Friedman addresses the letter to Kevin, thanks him for admitting he was wrong, and tells him she looks great. She says she’s in a healthier relationship with herself and that his rejection helped her discover inner strength. She also jokes about pegging and about reminding him every day that she doesn’t need him. This response shows that her comedy is often rooted in real experiences, and it suggests that she uses humor to process pain and to assert her independence.

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