This week, a woman fits some dates into a work trip in Aspen, San Francisco, and Los Angeles: 45, single, New York.
DAY ONE
10 a.m. Wake up to a sexy text, which is kind of typical for me. I’m a serial monogamist who’s been in several relationships, each lasting roughly five years. The last one ended seven years ago and I’ve been single since. I’m getting older, and also realized in the last three years that I don’t want children any more, or honestly, even a relationship, so now … I’m just looking for great sexual experiences and adventures.
10:20 a.m. I’m an advertising copywriter, so I work mostly from home and make my own hours. Looking in the mirror as I get ready for the day, I feel more confident than ever, and give fewer fucks about what convention might expect from me.
I’ve had a lot of fun recently, including going to a sex party. I went with someone I briefly dated — we never hooked up but he saw me on Feeld and invited me to this party; he goes to them a lot. It was at an apartment in Bushwick (of course). The theme was “neon” so the outfits were kinda tacky — Eyes Wide Shut it was not. That said, people were really friendly and open and once you kind of got naked and accepted why you were there and got into it, it was a lot of fun. I had sex with two guys that night. There was a basement area with a huge mattress where about 50 people were all fucking, but honestly once you start it’s just like having sex next to someone else having sex. The crowd was very young as well — I was one of the oldest people there and both the guys I hooked up with were in their 20s. I am not complaining, but … I don’t know. At 4 a.m. when people were standing around eating wings in the kitchen naked and drinking the dregs of the BYO booze, it kind of lost its luster for me.
2 p.m. I get a text from F describing in detail what he would do if we were in the same place at the same time. It’s filthy, and I love it. Sadly, he is in L.A. and I am in NYC — we met on Feeld. We exchange photos — his cock, my ass and tits — the usual. It’s a turn-on because when we are engaged in these exchanges it’s “live” — I know he’s jerking off and he knows I am, too. It’s very honest and raw. And he is really hot, which helps.
2:45 p.m. We’ve both orgasmed, and gone on with the day.
4 p.m. Texting with S, who is in an open marriage. We have had a few dates over the past several years after meeting on Tinder, sometimes ending in sex, sometimes not. He’s intelligent and fun and we get on really well. He isn’t in New York either. I tell him I’m heading to San Francisco for work — I have to meet with a client there — and he suggests I drop by his place in Aspen for a couple of days on the way. Fuck it, why not. I change and book some flights.
9 p.m. Laying around texting and swiping with new, fresh people. I don’t talk to any of my exes — I never think about them — apart from the odd text with a woman I had a relationship with years ago.
I’m into “people,” but mainly men. If I had to check a box I’d say I’m heterosexual. That relationship was a first for both of us; I’d say she identifies as heterosexual too (she is now married to a man with a kid). It was a lot of experimentation in what felt like a very safe place for both of us at the time. We were both pretty vulnerable back then — I was rebounding from a bad break-up, she had substance-abuse issues that she later sorted out in AA. It ended very badly — she wanted to move in and live happily ever after, I didn’t, and it was awful. I hurt her and I feel awful about it. We occasionally text about how cute her daughter is, where I am on vacation, but it’s rare. As for communicating with the men of my past, occasionally, I’ll experience a fleeting “if he could see me now” type of sentiment about my most recent ex who was a total asshole.
DAY TWO
10 a.m. I do Peloton today and most mornings.
11 a.m. Scroll through Feeld, Tinder, and Bumble. Read the news. Text friends.
11:30 a.m. I text F, and we have our usual morning exchange. He asks me to show him how wet I am. I oblige. We both come. He gets up and heads into work and I get on with my Zoom calls. We are both writers and it helps since the texts, while pretty one-dimensional, are hot and well-written.
1 p.m. Bored at work, I ask F if he would like to meet in L.A., seeing as I will be “somewhat” nearby while I’m in SF. It’s an easy flight. He agrees, and we make a vague plan. We have never actually met. I am beside myself with excitement and lust. It’s been almost three months we’ve been in touch and I know the chemistry will be insane when we meet. I make myself come, hard, thinking about this — then text him and tell him so.
9 p.m. Out having drinks. I bump into L, someone I never actually slept with but fooled around with a lot for three years. He has a terrible drinking problem. He is a mess, today, as always. He wants to hang out and come back to my place, but I tell him I’m tired and go home alone, leaving him at the bar to eventually make his way home to his long-suffering girlfriend. This takes a lot as, despite everything, I have been besotted with him for years.
DAY THREE
10 a.m. Nothing from F this morning. Focus on work. He is on a big deadline and I have my own shit to get on with!
11 a.m. S texts to finalize arrangements for Aspen. I am excited — this will be fun! Spend the rest of the day planning the work aspect of the trip in SF.
2 p.m. I take photographs around the neighborhood and just walk around the city.
5 p.m. Prepping for dinner. I enjoy cooking and grocery shopping and making food for myself. Both my parents are good cooks and I find the rituals of food preparation comforting and therapeutic. Tonight it’s roasted chicken and salad. Sometimes I make Indian food. Sometimes I make total trash like $2 ramen — it’s not all NYT cooking.
9 p.m. Contentment is something I’ve only really found in my 40s and I’m relishing it. Especially on nights like this.
DAY FOUR
10 a.m. At the airport. F texts to tell me how hard and horny he is but that he is late for a Zoom call — meaning he wants to come quickly. I reply that I’m at the airport. He says he is salivating at the thought of meeting me and I reply “same” because it’s true. But first, Aspen.
4 p.m. Arrive in Aspen. S picks me up and drives me to his place. I don’t think I’d quite understood how successful and wealthy S is. We are the same age. We chat like we’ve known each other for years, not just had a handful of dates. Drinking wine in front of the fire and talking about our lives, childhoods, and outlooks on life is nice. He is in an open marriage, and I don’t want a relationship, so there is no pressure on either side. We have sex in front of the fire. He loves anal, and I do too, so we do that and it’s great and then we just chill and watch TV. It’s incredibly relaxed and I can feel myself really unwinding.
DAY FIVE
10 a.m. We have sex in the morning. It’s really nice.
11 a.m. Try to keep busy today while S works and goes skiing later (I don’t ski!). My mom calls me this morning, while I walk around, and I vaguely catch her up on my life and romantic endeavors. My family lives abroad and I don’t see them much. They’re conventional — everyone is married, they’ve all bought a house, own a car, have kids. I think my mom has given up hope of me “meeting a nice man.” Which is fine with me.
12 p.m. Walking around the town of Aspen, I’m reminded how good I am at traveling alone. Friends, I see all the time in New York. They are pretty much all coupled up and they seem to enjoy my salacious tales.
2 p.m. A phone call with my best friend in New York. We have a thing where we have nicknames for all the various men we are seeing. For example: “One for the Road,” “Paul the Murderer,” etc. Sometimes I think my friends think I am a bit too wild. I think some of them wish I would settle down. Some of them know my last ex from seven years ago absolutely destroyed me so they are kind of protective.
7 p.m. S and I go out for drinks. We share more stories about our lives. It’s fun and light-hearted, then we come back and cook steak on the BBQ.
9 p.m. After dinner we chat over wine and then watch some comedy on TV and go to bed early. We just go to sleep. He’d been skiing during the day, and we had both had a lot of fresh air and a fair bit to drink, so we’re both fine with crashing.
DAY SIX
10 a.m. Leave Aspen. It’s been awesome — S and I tell each other what a great time we’ve had. I kind of just know we won’t communicate for some time now, and that’s fine. Now some intense work — I am ready for it as I’m rested and feeling good.
2 p.m. Once I’ve landed in SF, I quickly check into my hotel and then head to a half-day work conference.
10 p.m. Work is done and I decide to meet D, a guy I just matched with on Feeld, for a drink. We hit it off instantly. Insane chemistry and great conversation.
3 a.m. He’s showing me around SF in the middle of the night. The city feels like it’s ours alone. It’s so fun.
5 a.m. We go back to my hotel and have really good, intuitive sex until the sun comes up.
DAY SEVEN
7 a.m. He goes to sleep while I power through a couple of East Coast work calls.
2 p.m. We don’t really want to leave each other but sometimes it’s good to end these moments when they are at their best. D offers to drive me to the airport. An hour after he leaves he texts to say our night together restored his faith in humanity.
6 p.m. Just like that, I’m arriving at my hotel in L.A. and getting ready to meet F. I haven’t slept but I’m buzzing on adrenaline and super excited. I take a shower, get ready, and head to the hotel bar.
7 p.m. F arrives. I notice that we are both trembling as we say hello. I start rambling about my day — it’s nerves, lack of sleep, white-hot lust and adrenaline. He kisses me, hard. That shuts me up! Twenty minutes later we’re in my hotel room having the most mind-blowingly good sex, possibly, of my entire life. We keep telling each other how good it is and I come over and over. We are sweaty and exhausted, It’s all incredibly heady. At some point we take a break for a beer, then I have him spank the living daylights out of me.
9 p.m. Afterwards, we chit-chat a little and he leaves. A kiss on the lips feels kind of … I don’t know. Nice? Funny? Weird?
Collapse into the bed with a big shit-eating grin on my face. What a week!
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