This week, a woman tries to balance her desire for a serious relationship with her newfound interest in group sex: 30, single, Philadelphia.
DAY ONE
8 a.m. I wake up and immediately think about how this week marks one year since I left my husband. Up until that point, he was the only person I had ever had sex with. We met when I was 18. Eleven years later, I filed for divorce.
We split not long after I found out he was cheating on me. I was watching the news on his laptop, which was also connected to his phone, when the messages started coming in. It was very clear he was hooking up with a co-worker. My immediate feeling was shock, with an undercurrent of relief.
It wasn’t like things were perfect. I always felt like I had a higher sex drive and a kinky side, but never explored any of it because it seemed pure fantasy. Sex was quarterly and vanilla. Looking back, our lack of sexual chemistry made me feel undesirable and fearful that if I divorced him, my sex life would get even worse.
10 a.m. At work; I’m an event planner for a college in the area. I open up Tinder. I joined it a few months after separating. The hookups began, and before I knew it, I was also on Feeld, the kinky hookup app. It has been a year of self-exploration, both physically and emotionally. I now unicorn for a married couple and have a few friends with benefits and other hookups.
2 p.m. The Couple messaged me to talk about the upcoming orgy they’re hosting and tell me that one of my former hookups, Finance Bro, still plans on coming. I got Finance Bro an invitation to the orgy when we were still seeing each other consistently, but I haven’t talked to him in more than a month. I’m a little hurt that he’s reaching out to them but not me. I’m nervous about seeing him there. There had to be a reason he stopped messaging me, and I feel like I’ll be wondering the whole time if he’s having more fun with the other women there than he did with me.
6 p.m. Talking to my friend about Finance Bro. I actually liked him. He asks thoughtful questions and is nice and really hot! But his actions don’t communicate a similar interest beyond a hookup. I decided this orgy is the last time I’m going to see him. I just hope I don’t lose the Couple in the process! They’ve been in the market for a new guy unicorn, and if Finance Bro becomes it, that will be hard for me.
9 p.m. I’m tired because I actually hooked up with two guys last night! It started with terrific sex with my main FWB, an engineer who DJs. We’ve been seeing each other for almost a year now, and the sex is always mind-blowing. Afterward, I finally met up with the Surgeon, a man from an app I’ve been texting with for a while and also had incredible sex! He’s fun to hang out with and I think there could be dating potential.
DAY TWO
9 a.m. I’ve been texting the Surgeon a lot about the orgy tonight … he loves that I’m going. I also tell him that I’m feeling a little jealous about Finance Bro joining the orgy — I’m an open book and he knows a bit about my past with him — and he reassures me that he couldn’t imagine having more fun with anyone besides me, which was sweet and boosted my self-confidence.
1 p.m. I run a meeting for two big events we have coming up. I actually run several regular meetings, and this one is by far my favorite. I always leave them feeling empowered.
5 p.m. The Surgeon keeps bringing up joining me in group sex in the future, which makes me feel like I’m being used as a means to get into this “lifestyle” world. I tell him that after this orgy I don’t see myself doing too much more, that I’ve learned I prefer one-on-one.
8 p.m. I try to catch up on work for a few conferences that I’m in charge of, but it’s hard to concentrate because the Surgeon won’t stop texting me. I’m texting right back, and we do this until we both fall asleep.
DAY THREE
9 a.m. I wake up to more texts from the Surgeon; I like the attention.
11 a.m. I have brunch with a friend, since we both technically WFH and I can make my own hours on most days. I don’t talk with this friend too much about my sex life. It was refreshing to focus on other things.
2 p.m. The Surgeon is trying to make plans. He’s on call, which means I’ll need to come to his place again. He says he doesn’t want it to seem like he’s not putting in the effort, but he’s playing pager roulette since he can get called away at any time. I said I’ll take my chances.
6 p.m. Heading to his place. It’s all very chill and laid-back; he’s just doing some dishes. I’m like, “You could get paged at any time — let’s get to it!” I do like him, which scares me.
7 p.m. We finally get to having fun. The stress of a pager possibly going off is actually kind of a thrill! He takes charge and I love it. He is dominant yet passionate. One moment he’s holding my wrists down so I’m completely at his mercy, and the next it’s all intimate eye contact and touching. We even have great pillow talk before I head out.
9 p.m. I text with the Surgeon that at some point we actually have to go out and get drinks.
DAY FOUR
10 a.m. The Couple asks if the Surgeon might be interested in group stuff, and I said he certainly is. I’m kind of worried, though, that my wild side is holding me back from being a serious dating prospect.
Noon. Making plans with the Pilot for tomorrow. He’s an incredible FWB and always treats me like a princess. He pays for dinner and is the best ever at oral. Plus he’s so cute!
2 p.m. Our biggest event at work is around the corner! We have an event walk-through this afternoon to make sure we are all set. Thankfully, we’re good to go.
5 p.m. My ex-husband emails me. Apparently he has been getting charged for home insurance even though we sold the house months ago. My name is on the account and he wants me to do something about it. I don’t want to deal with him or any of this. It’s very annoying, and issues like this seem to go unresolved between us more than I would like.
8 p.m. I still haven’t heard back from the Surgeon since we hooked up yesterday. I know his job is crazy, so I’m trying to be patient, but we went from texting a lot to suddenly nothing. This is why I’m afraid of getting emotionally attached to someone! I worry I got caught up in this guy too early.
10 p.m. Feeling super-unwanted and low right now. Maybe the Surgeon acted like the group experience I have was interesting, but has since ruled me out as a serious person because of it. It has happened before, and this is why I hesitate to tell guys when they ask.
DAY FIVE
6 a.m. Despite being one of the top Taylor Swift listeners on Spotify last year, I hardly listen to her anymore. She is my therapy, and for a while I felt like I didn’t need it. This morning, though … back to Taylor. Nothing from the Surgeon.
9 a.m. Try calling the home-insurance company to switch the name to my ex-husband’s account so he can deal with it. I don’t want to fight this battle for him. It’s not my fault he just now realized he’s been getting a monthly charge for a service neither of us use.
2 p.m. Finalizing plans to see the Pilot tonight. It’s my turn to go to his place, and he has dinner reservations set and everything. Even though we are strictly friends with benefits, it’s nice to be taken out. He’s cute and charming, and I have incredible sex with him, but I’d exchange it all just to hear back from the Surgeon. I’m so embarrassed I let my mind and heart wander through this and get my hopes up so quickly. I’ve been on at least 60 dates this year and have developed feelings for only three guys. None of the three have reciprocated the feelings. It makes me scared of dating.
6 p.m. Dinner with the Pilot is of course a good time. He dresses impeccably, is friendly with all the staff there, and we have such great conversations.
7 p.m. We get back to his place and cuddle. So simple but so comforting. I never did this with my ex-husband. After a while we start making out and just linger, kissing and touching each other, taking each other in and savoring every moment. He has the softest lips, touches me sensually, and has these soft moans that just make me melt. I could make out with him forever. We slowly progressed to oral, and when he went down on me, I felt like I could die.
Good God, I wish we had enough in common to date. I could have sex with him every day for the rest of my life and never get tired of it.
It’s so wild how different our lives are. He went to parties with drugs, sex, and alcohol in high school. My idea of a high-school party was pasta nights before a big cross-country race. He was the popular guy and I was the class president.
10 p.m. I’m about to drive home and see I got a text from the DJ. After tonight, I’m feeling a little better about the Surgeon. I have two other hot, intelligent guys hanging with me.
DAY SIX
6 a.m. Still nothing from the Surgeon. I’m feeling a strong urge this morning to download Hinge to start meeting other guys who might be dating potential. However, I know I’d just be doing it for the dopamine hit.
1 p.m. Therapy. My therapist seemed to glaze over stuff with the Surgeon. She knows that I know I’m overthinking this. We were only talking for a month, after all.
4 p.m. Looks like the orgy is canceled. The Couple is pregnant! I text Finance Bro about it. He responds quickly, and I write back quickly, and then get nothing. Good-bye, Finance Bro. I just know that about myself: I don’t do well with inconsistent texting.
5 p.m. Jersey Shore guy enters stage left! I saw him consistently for months, then suddenly that all stopped. Haven’t talked to him in nearly six months. We caught up a bit; he likes hearing about guys I’m fucking and I don’t mind talking about it, especially with him. He’s 100 percent not a dating prospect. He could legitimately be a cast member on Jersey Shore. He’s hot, he’s fun, but he’s not someone to take seriously. Hopefully we’ll set something up soon.
8 p.m. Downloaded Hinge for the dopamine hit. It worked … trying to keep up with all the matches and messages!
DAY SEVEN
9 a.m. Despite swearing off Finance Bro, he texts me and I take the bait. He says he has a girl he thinks he and I might have fun playing with. Apparently she’s wild. The thought of the old hookup (me) joining the new hookup (her) sounds horrible.
I go along with it and say it sounds fun.
1 p.m. No response. It feels so demeaning to me.
6 p.m. I am supposed to get dinner with another doctor tonight, but that ends up getting canceled because of his work stuff. I treat myself to takeout from the vegetarian Chinese place near me.
8:30 a.m. I hear from the Surgeon. It’s a fairly basic text. I write back right away. Now I’m full of anxiety again.
11:45 p.m. He hasn’t texted back. I block his number and feel a surge of relief.
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