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This Week’s Sex Diary: The Ex-Orthodox Jewish Mom Hooking Up With Four Guys

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Illustration: Marylu Herrera

This week, a divorced mom has sex while her kids are away: 32, single, New York

DAY ONE

7 a.m. Inundated with new matches on the kinky app I prefer as a proud, self-pronounced “divorced whore.” Faceless guys show off their cocks and nothing else, like it’s their entire personality. Maybe it is. Other guys, like A., opt for their glistening chests on beaches. Their bios read, “Witty banter to the front.” Talk is cheap. Do they dare to lick my translucent stretch marks?

I had twins when I was 24. I grew up Yeshivish Jewish, a level up from traditional Orthodoxy, in Lakewood, New Jersey. I no longer identify as a member of the Yeshivish community. I strongly identify as a deeply spiritual Jew with a close connection to God, but … I needed more freedom with sex. In the Yeshivish world, female pleasure is not prioritized. I never imagined I’d be divorced at 30 after 11 years of marriage, but I had to get out of that life bound to a patriarchal loser!

9 a.m. Match with A. just to tell him he’s boring, then I unmatch first. I can’t handle rejection.

10 a.m. N. texts, “Good morning, cheeky girl.” A mere notification from N. could kill me. We’ve been dating for six weeks. He’s different from the other guys I hook up with — special. We do silly dances in the street. I cry every time we have sex because I actually feel an emotional connection.

N. touches, licks, penetrates, and speaks to me profoundly. He’s the opposite of my ex-husband, Dave, who used ChatGPT to write me birthday cards and whose mechanical nature made me feel like I was having sex by myself. When I rode him, with my blonde curls sweaty and wild, Dave would meet me with a monotone “Fuck, your tits are hot.” Hearing that always reminded me of when I was breastfeeding, when Dave would say the twins’ lease on my tits was expiring. How barbaric — the ownership of my tits, like they’re NYC real estate and he’s the CEO of Tishman Speyer. But he is not. And my tits aren’t even my best asset.

10:05 a.m. I respond, “Stop flirting with me, you’re being inappropriate.” N. writes, “Sue me, xo.” I’m a lawyer, by the way, and currently in the office in midtown. N. is a gorgeous, intellectual writer with blue eyes and scruff.

1 p.m. On a call with a client I’m helping pro bono. A bisexual pilot, whom I will never meet because he lives in France, sends me an unsolicited video of his butthole. I ignore him.

4 p.m. Get an iced hazelnut latte from the deli across the street. Four Equals. Regular milk.

5 p.m. Writing an appellate brief. The bisexual pilot texts, “Babe?” Ignore.

5:15 p.m. Match with R. His bio says he’s a six-foot-three 43-year-old molecular biologist looking for earthy, feminist, witchy beauty. Despite having an NFL player’s physique, he’s a dork who’ll appreciate my curly bush. I send him a video singing “Once an Austrian Went Yodeling.” I want him to see how strange, hot, funny, and unique I am. I’m not just going to sing some sexy Sabrina Carpenter song. I must sing the best song from my favorite childhood movie, Wee Sing in Sillyville.

9 p.m. My parents are babysitting. I tell them I’m going to “Tali’s house” for dessert. In the past, that is what I would have been doing — wearing a frumpy skirt and gossiping with Dave and our friends about poor single community members. I felt displaced, pining to be at a queer speakeasy making out with an androgynous person who smelled like Abercrombie cologne. Now that I am a poor single community member, I’m going to meet R.

9:30 p.m. R. picks me up over his shoulder and carefully puts me down on his bed like I’m a sleeping newborn being placed in a bassinet. He undresses me, then sits in front of my vagina for hours, massaging my clit while telling me how beautiful I am. I come again and again.

11:30 p.m. R. asks about my religion given that I grew up so observant. Ugh, why? I tell him I love bagels, then sing him the aleph-bet while flailing around his room, the same way I used to perform as a 9-year-old for my parents.

DAY TWO

6:30 a.m. The twins request Mickey Mouse pancakes. Cooking violates Shabbat, but God and I have an understanding. I have done everything bad, yet I still feel God dancing in my bones.

9 a.m. R. texts, “I love your Star of David tattoo more than your armpit.” This warms my heart, but I don’t want to get too deep, so I respond, “lol, ily!” I do love that he is attracted to my Jewishness. It’s a huge part of my identity. But I don’t see a future with a non-Jewish man. I’ve broken away from the Yeshivish world — not the Jewish world. I also have this kink for rejecting people, being mysterious, and enjoying them being obsessed with me.

11 a.m. The bisexual pilot sends another video of his butthole. My butthole features a deflated hemorrhoid from my pregnancy, can you believe this?

3:30 p.m. At a museum patrolling the twins. N. texts, “You are truly wonderful,” followed by a GIF of the green Teletubby running in a field of flowers. I respond, “I long for you,” and instantly regret my choice. What if he stops liking me because I’m too much?

9 p.m. Masturbate to a casting-couch porno. A dude with a veiny hand instructs a blonde to open up so he can inspect her vagina. Despite my inexperience with women, I feel queer because I love a cute vagina just as much as a big veiny hand.

10 p.m. Eat a slice of cold pizza. Wish for N. to hold me saying, “That’s my baby,” as I fall asleep.

DAY THREE

9 a.m. Take the twins for breakfast. Daydream about N. feeding them cinnamon-raisin bagels with cream cheese and calling them “sweet little birds.”

“Night Fever,” by the Bee Gees, is playing. The twins dance. In seventh grade, I masturbated to John Travolta circa Saturday Night Fever. I came so intensely to his scenes with women in vintage red cars, mentally replacing them with scenes of me having sex with my yeshiva’s rabbis in vintage red cars.

1 p.m. At a rock-climbing place with the twins. M., some finance buffoon, texts, “I haven’t stopped thinking about your mouth chewing that Sumo orange at Friedman’s.” The last text I sent to M was two weeks ago, thanking him for feeding me that Sumo orange. Blocked.

4 p.m. Haven’t heard from N. Even though it’s only been 24 hours, I believe I’m being ghosted. It’s too early to know. Ghosting is crazy. You communicate that you miss them dearly, they don’t answer, and only after time has passed do you realize you’re completely irrelevant. I make up an elaborate fantasy about where N. is: the Mandarin Oriental with another woman, having better sex than he has with me, an inexperienced loser with a lame vagina.

10 p.m. Lying awake in my bed, which smells like lo mein because I’m filthy. Judging N. for his horrendous actions in the story I manufactured. How dare he get a couples massage with that skinny woman who’s nothing like me!

DAY FOUR

7:27 a.m. A text from F., some engineer I matched with who I think is lying about his hairline: “Confirming our first date tomorrow? I thought about you yesterday.” Ugh, this dog loves me too much already.

Noon. N. tells me he’s downtown for a meeting. I’m not being ghosted! I suggest we kiss on the sidewalk before. He says he’d love to “suck face.” I’m wet.

1 p.m. Charge toward N. like a cheetah. He picks me up, spins me around, and kisses me warmly. We’re figure skaters who are in love. We must go to the twins’ next birthday party dressed as figure skaters and make everyone uncomfortable, especially my ex’s mom.

5 p.m. With K., a 26-year-old stationery designer from London whom I met on the app, for an early dinner. Not much beneath his surface, but he’s hot, so after I meet my girlfriends for dinner at eight, I’ll meet up with him to have sex.

8 p.m. Dinner with the Yeshivish girls at Abaita. One of these girls told my ex that if her husband treated her the way he treated me, she would run him over with her Prius. Good.

8:30 p.m. The girls tell me I’m talking too loudly about my sex life. We shift to talking shit about people.

10:30 p.m. I have sex with K. on the fourth floor of the Maritime Hotel, which looks like a cruise ship. His penis is four inches and smells horrible. I cannot wait to get out of here!

Midnight. What are the twins dreaming of? I cry myself to sleep thinking of the days I spoon-fed them homemade chicken soup.

DAY FIVE

9 a.m. NYSC to work out. Make eye contact with a buff trainer for the duration of my run. He’s ugly, but I’m enjoying this game. I hope he feels rejected when I walk past him later. I don’t know why I’m so mean, but I am, and I won’t work on this in therapy because I need to work on my other bad qualities.

Noon. Send F., the engineer I think is lying about his hairline, a picture of my sweaty body hunched over a stretching table from this morning. Caption it with the clown emoji. He responds, “Jesus Christ, you’re so fuckin’ hot.” I can feel my attraction for him dissipating because he is obsessed with me. I respond, “Jesus is mid lol see you l8r.”

4 p.m. N. smokes pot on FaceTime wearing a black T-shirt that says something in French — I don’t know what, I’m not very cultured. He knows I’m actively dating, but I’d happily stop when I’m tired of being a whore. I would love to be in a relationship with N. and maybe feel his embrace for the rest of my life.

8 p.m. F. parallel parks his Mercedes right in front of my building. One of his wheels is on the sidewalk. I call him a “bad kitty” and randomly say “meow” as we walk to a bar down the block. I hope he’s embarrassed and obsessed with me.

8:30 p.m. F. finger-blasts me in the bar bathroom.

10:30 p.m. F. finger-blasts me in the back seat of his slanted Mercedes.

10:45 p.m. F. fucks me in the back seat of his slanted Mercedes.

11:30 p.m. Falling asleep naked. Feeling shitty that I used F. for sex knowing he’s really into me.

DAY SIX

10 a.m. While working out, I match with more guys. They all initiate conversation by complimenting my big blue eyes. They are trite. I sext them all anyway. I see that buff trainer staring at me. I hope he can tell I’m cheating on him.

Noon. Meeting my female colleagues for lunch near the courthouse. They’re all smarter than me, but I have a great personality. I have many talents. Ugh, it is very hard to have such a huge ego but such low self-esteem.

12:05 p.m. I tell N. about my day and he says, “I am so proud of you, honey,” like we’re married. I picture our first dance to a song he chose. I know my feelings for him are big when I think about how selfless I am with him compared with how cunty I am with others.

4:45 p.m. I send N. a hilarious Reel of a man having a sarcastic conversation with AI where the AI doesn’t get it, but N. ignores me. Fuck my life.

8 p.m. While wearing a face mask, I sext three of the guys I matched with. Not a single one mentions what they’d like to do with my clit, so I unmatch. Clit is life. Bye-bye!

1 a.m. Cry myself to sleep thinking back to the day the twins were born. The most beautiful creatures that I tandem breastfed for two years.

DAY SEVEN

7 a.m. F., Mercedes fucker, texts me, “I can’t stop thinking about you.” Being overly wanted feels insufferable.

10 a.m. Haven’t heard from N. I’m sure he’s ghosting me. Make up a new story that he’s back at the Mandarin Oriental eating the ass of an ex he told me was his “sexual awakening.” This is obviously unfair because N. is my sexual awakening. There will always be an uneven power thing between us, which makes me feel like I need the upper hand in something else — maybe that everyone wants to be around me all the time and he can’t say the same. I need therapy for the way I turn relationship dynamics into competitions, but I can’t deal with that right now because, again, I’m in therapy for other bad qualities.

1 p.m. Call with a client who shared a lot about their personal life. The call makes me appreciate the human component of my work even though I sometimes want to move to the mountains and be a dog walker and writer and not talk to anyone.

5 p.m. R., a stranger with 30,000 Instagram followers, FaceTimes me while I’m at the office. In the frame, his cock appears to be the same size as the bookcase in front of him (Kafka and a plant. Brooklyn, obviously). “Show me your tits, princess,” he says in a British accent. Like the colossal slut that I am, I tear off the gray collared sweater I deliberately chose this morning to look professional and flash my pierced nipples at him. My armpits smell like they’ve had a day. He grunts, “You’re a hot little whore.” I laugh like a hyena and hang up on him.

8:15 p.m. Masturbate to the thought of N. and I having missionary sex and my friend watching us and touching herself.

11 p.m. Cry myself to sleep. Despite my obsession with freedom, I miss the twins when they’re not here and wish to hold them, smell them, and sleep with them in my arms.

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