In this week’s story, a newly divorced woman makes plans with a famous reality star, a photographer, a cinematographer, a musician, and a celebrity stylist: 37, single, Los Angeles.
DAY ONE
7 a.m. Wake up early to drive to the Erewhon in Calabasas for an iced coffee before taking care of my friend’s baby, Cassandra, for the day. I’m a film professor in London, but my friend Aurora invited me to spend the summer living with her and her partner in Topanga Canyon in exchange for helping out with child care, so I’m a glorified nanny until the semester starts up again. I’m also processing my recent divorce from my ex-husband, Joe. We were best friends and creative partners and then his mom died last year and he began therapy and just decided he wants a fresh start. He also met another woman — it’s been pretty excruciating!
9 a.m. I get a text from the Photographer, who lives in Wyoming and just got back from an assignment in Tanzania documenting Jane Goodall’s chimps or something like that. We’ve only talked on Raya, but he’s going to be in upstate New York around the same time I’m there for a wedding next week and he’s hoping we can meet in person. Honestly as ridiculous as this app is, it’s been a lifesaver. I’m not looking for anything serious but don’t want to waste time meeting randos, so I appreciate how you have to be verified and semi-interesting to be on it.
12 p.m. Sweet baby Cass is napping and I’m trying to write this screenplay I’m working on but really just making a third iced coffee and reading horoscopes, while texting back several friends in London. (Joe and I had been living there, but now the only thing keeping me is one more semester of teaching.) I’m also texting with the Influencer, a ripped, classic midwestern guy who was a finalist on a dating reality show but now is just … an influencer. He’s the opposite of my type, but he’s so hot.
3 p.m. Solidify my evening plans with a friend who works as a costume designer, and text the Cinematographer I went on a date with last week. He talked a lot about himself, but I was caught off guard by a passionate good-night kiss that drew me in. I tell him I’d like to kiss him again. He responds right away; looks like I’ll have a nightcap with him.
5 p.m. Yoga here in Topanga. Afterward I text the Musician confirming our date tomorrow. He’s handsome, sensitive, and works in advertising but wants to play music full-time; a good combination of practical and sensual. He’s seven years younger than me, but he seems to have good manners. We’ve gone on two dates; what we both thought was just a hookup has seemingly turned into a little more since we genuinely get along.
10 p.m. Meet up with the Cinematographer after my dinner. He arrives at the bar, we have one drink, a little basic chat, and then walk back to my car. Suddenly we are making out like teenagers in the passenger seat and he’s telling me how sexy I am, how much he wants me, etc. After a while, I pull back. He asks if I’m thinking about my soon-to-be ex-husband and I don’t really answer, but the truth is I’m thinking more about the Musician. I decide to head home. This was fine, I guess, but I don’t need any more of it.
DAY TWO
10 a.m. A morning of watching baby Cass.
2 p.m. When Cass’s parents get home, I head to the beach for a bit just to do nothing. Before I know it it’s time to get ready for my date with the Musician. He’s made a plan for us to watch the sunset and then get dinner.
5 p.m. As I get ready to meet him, I know (and he knows) that I will spend the night with him again, so I pack accordingly.
8 p.m. Sunset with him is sweet. We get dinner at a place in Eagle Rock that a college friend founded and where the Musician also knows the head chef. So now we sort of have friends in common, which feels cute, and the tapas are delicious. Afterward we go back to his house and take a long night walk around the neighborhood.
11 p.m. Now he’s playing me guitar and he’s surprisingly good! Eventually I ask him if he wants to kiss me, because he’s not making any moves. He gives me some of his deepest eye contact yet and says, “Yes I do, very much.”
11:30 p.m. We are kissing hard and he’s on top of me, we are fully clothed but it’s so intense — our kissing and holding each other sometimes makes me feel on the brink of tears. We go back to his bed and get naked, we’re fucking and it’s deep and raw (as raw as you can be with a condom) and my nails are in his back and he comes faster than he wanted to and I say “Awww, I love you!” by mistake, but we laugh about it.
DAY THREE
9 a.m I drive home to Topanga early this morning; I think today will be lazy. I write a bit and lie in bed resting. I never sleep that well when I spend the night with a new person.
12:30 p.m I get a text from the Celebrity Stylist. We spent the last month having good, casual, regular sex before he had to go back to New York City for a job; because of his work, he’s legitimately bicoastal. He wants to know if we’re still on for our date on Monday night; I’m planning to see him before I go upstate for this wedding (and to see the Photographer). I confirm yes! I like him, but I know I won’t catch feelings for him. It’s too bad given the sex is pretty incredible.
3 p.m. Day of “me time” is over as I have to watch the baby for an hour or so. She’s in such a good mood, it’s adorable. I love her so much. Make the mistake of checking my phone and see that I’ve got an email from the divorce mediator in London that Joe and I are working with. She’s helping us divide our finances (we’re very entangled from collaborating on several film projects) and I feel a pit in my stomach. I am still in shock that this is happening.
4:30 p.m. Preparing course work for my college students for the upcoming semester and feeling grateful I have something to ground me. My friend Melanie — who’s been staying here in the pool house with all of us this summer after finishing grad school — pokes her head in as I’m wrapping up. It’s time for our collective “family dinner” down the hill at the local pizza place that has bands play on Thursday nights. I get dressed while she complains about her mom and I appreciate the distraction.
DAY FOUR
11 a.m. Day off from watching Cass and I use the morning to write. The screenplay feels like it’s about two-thirds of the way there.
5 p.m. Drive to the yoga studio for a session but the class is full so I wind down the canyons to the beach and walk in the waves a bit to clear my head.
7 p.m. Grab dinner with girlfriends at an Italian place in the Musician’s neighborhood. I message him afterward that I’m around and for a bit we go back and forth; he’s at dinner with a buddy but in the end I’m tired and don’t feel like waiting for him to wrap it up.
9 p.m. I drive home a little bummed and lonely (worried I like him already and relieved I’m going to New York for a week to escape the feelings).
9:30 p.m. I cry in the car thinking about my ex and how no relationship I ever have again will be so pure, and almost naïve, as what we had.
11 p.m. The Cinematographer texts: He wants me to put him in my mouth. I don’t respond.
DAY FIVE
8 a.m. Wake up to a text from the Influencer, canceling our sunset-swim date tonight, which would have been our first meeting: He’s hungover from doing psychedelics yesterday. This stings at first, and then it feels liberating. I need a night alone.
1 p.m. I decide to swim naked in the pool here as Aurora and the family have gone to Napa for the weekend.
2 p.m. I take a few “erotic” photos of myself and stow them away in a new album I call “Portland.” I met a very beautiful man there a few months ago at an environmental conference I went to for fun; he was the first person I slept with after Joe. I send him occasional photos to remind him of me, which he loves. He’s my most special one, but I’m waiting on that, the timing isn’t right for either of us …
3 p.m. Screenshot the text exchange with the Influencer and send it to Aurora after she inquires about how the date is going. She responds “sooo LAAAAA!” Somehow I feel like I’ll never hear from this guy again. Ugh.
8 p.m. Write more of the screenplay and drink mint tea in bed thinking about some combination of the Musician and Portland guy. The moon outside looks full and I hear the cooing cicadas and a cacophony of wild-animal sounds from the canyons and I feel a deep sense of peace.
DAY SIX
10 a.m. Pack and shower — taking a red-eye tonight.
1 p.m. Get some messages from Joe about practical apartment issues and feel sobs coming on — will this ever get easier?
3 p.m. Text the Musician a photo of my legs on the beach from earlier in the week and tell him I’ll message him when I’m back from the city.
7 p.m. I decide to lean into my heart and text Joe a simple message that I’ve expressed to him a million times before in person but somehow want to put in writing now that it’s been several months since we’ve really talked: Hi Joe. Thinking of you always, I hope your exhibition went well. I love you — even up until the moment of signing the papers; I will always want to make it work with you, just say the word. But otherwise of course I will proceed accordingly with divorce plans …
DAY SEVEN
8 a.m. Arrive at my hotel from the red-eye. They have a room all ready for me even though it’s early, which is sweet. I’m on the LES and love the sweaty summer energy swirling around me. Joe and I had our first dates here after we met at a gallery event and I’m trying to hold onto the beautiful memories of our love as I walk the streets with my headphones on, even though they are painful.
10 a.m. The Celebrity Stylist texts to ask if we are still on. I’ll respond soon but need to nap first …
10:30 a.m. Wake up after 30 minutes and there’s new messages from him. (It’s two photos: one with his mouth and a thermometer of 100 degrees, then one with a COVID test showing a positive stripe.) “I’m so bummed! I’ve been looking forward to fucking you in Chelsea for weeks now.” I’m surprised how little I mind him canceling!
11 a.m. Hop on Raya and send texts to a few guys, all based in the city. They all respond, but I decide to make a date with the first one, who’s a civil-rights lawyer. It’s pretty clear from my message of “only in town for one night” what will happen. Just as he and I make plans, I match with a famous musician in Brooklyn who asks me what I’m up to later. Now this could be interesting. I am going to keep talking to both and see how the night plays out.
2 p.m. I spend the afternoon shopping for dresses to wear to the wedding and rehearsal dinner. The shop girls are friendly and chatty and want to know my story, so I share that this will be the first wedding I’m going to stag after being married for eight years. They cheer me on and tell me I look like a million bucks, which helps somehow.
5 p.m. Visit my friend Annie in Brooklyn to meet her new little baby, who is just the cutest, and tell her I’ve made the recent decision to freeze my eggs. She’s supportive but also remembers that Joe and I never wanted kids. Something about this breakup and baby Cass has made me reevaluate everything and now, who knows? I might want the option.
9 p.m. The chats with the Brooklyn guy fizzled so I’m heading to meet the Civil-Rights Lawyer for a drink. When I arrive he’s already there waiting for me, and is gorgeous in person. We talk for a few hours with intense eye contact and lots of leg touching. After a game of pool we walk back to my hotel. We make out on the street and he asks if he can come up. We get to my room and immediately undress. He goes down on me while I lie on the bed and then puts on a condom and takes me from behind. I come so quickly. After he finishes we lie holding each other and panting. We talk a little bit and then he leaves — phew. I need to be alone, realizing that Joe has not responded to my message from yesterday.
11 p.m. I turn out my light thinking about Portland man and then remember that in the morning I need to message the Photographer about how I’m looking forward to meeting him upstate. Maybe we’ll go for a walk in the woods … you never know, I’m always open to meeting the next love of my life!
Want to submit a sex diary? Email sexdiaries@nymag.com and tell us a little about yourself (and read our submission terms here.)
