This week, a woman texting an old standby and reconnecting with an older man she met on vacation: 30, single, Brooklyn.
DAY ONE
10 a.m. While starting my day, I receive a random email from J, an older guy I met in England a few months pre-COVID. Back then, I was in a relationship and he was married. He has since divorced and spent the summer settling back in New York. I’m a life coach but also offer private yoga lessons for high-paying clientele. He wants to have a private yoga/healing session with me.
After a little bit of thought, I ask J if he wants to swing by my apartment later tonight to see what’s going on with him; I tell him it will be no charge. He quickly says yes. I kind of forgot what he looks like, so I do some IG stalking and see he is even hotter than I remember!
3 p.m. Wrapping up emails from a co-working space and planning to go home soon and hit the gym, then tidy up my apartment.
6 p.m. J arrives and it’s fun to connect. When we first met, I was on vacation with my ex, A. We happened to run into J one day; he and my ex were childhood friends who lost touch. The chemistry between J and me was obvious, and my ex accused me of flirting. We had a minor fight, but I figured I would never see J again, so I wasn’t really concerned.
My ex was a poor fit for me beyond the bedroom. We experimented with BDSM and tried out tantra. The sex alone was not enough to keep me fulfilled; when I eventually started to text other men, a few months after that vacation, I knew it was time to call it quits. We run into each other at concerts and hang from time to time, but I have no interest in engaging further.
7 p.m. J arrives at my place. He has some physical pain I lack the knowledge to help with, so I refer him to a friend. We wrap up and he mentions grabbing a bite to eat. I look up a nearby spot I have been meaning to try. I am enthralled to learn more about him. I’ve never slept with a bisexual man — or someone who’s been married before.
9 p.m. Once we sit down at a restaurant, I’m ready for some wine. It’s apparent that we are both foodies and accidentally order half the menu. He explains what brought him back to the States: a tumultuous relationship with his soul mate that ended with her sending him back home after six years in London. They’re divorced and see other people, but are still entangled to an extent. He tells me about his time in England and the sexcapades with his ex-wife, bringing other men to bed and sending her to sex clubs so he could hear all the sultry details. I am so intrigued. He talks about sex in such a comfortable, non-creepy way.
11 p.m. I don’t tell him this, but I am ever so happy to ethically release him as a client so I can see how this plays out. We hug good night.
DAY TWO
12 p.m. I work from home today, so after a while I take a walk to meet my best friend and pick up her 6-year-old daughter. We met in London years ago because work used to send me there a lot. We roam around Park Slope and go to Barnes & Noble.
6 p.m. Out with some girlfriends for happy hour. I get tipsy and start drunk-texting, looking to hook up. Suddenly, J is top of my list. He doesn’t respond, so I go through my contacts. I don’t hear back from anyone worthwhile, so I text G, who I’ve known since high school; we hooked up one summer when we were still virgins. We reconnected a few years ago and it was fun, but now I only call him if I am really bored. He is the worst fuck buddy I have ever had; he constantly stands me up.
9 p.m. G sends an Uber to get me. He is a doctor and likes to brag by sending me screenshots of his pay stubs. When I get there, we sip some whiskey and before I know it, we are rolling around on his carpet. It’s obvious he has been hitting the gym and I am digging his firmer body. While this is far from romantic, it’s still fun.
We have a good rhythm and it’s rare I feel a guy pulsate inside me; it’s an incredible turn-on. We fuck twice and eventually pass out.
DAY THREE
10 a.m. We wake up and start chatting. He reveals some conservative viewpoints that strongly contradict my own beliefs. I find myself getting nauseous, unsure if I drank too much or am truly sickened by his existence. I’m ready to take my Uber ride of shame home.
3 p.m. J texts and suggests a drink at the new rooftop hotel bar that just opened downtown. I tell him I’m a Yelp Elite and love reviewing new spots.
6 p.m. I meet him at the bar and he offers to grab drinks. I appreciate the gesture. I’m 30 and he’s pushing 50, so I enjoy the part of this that feels scandalous.
The bar is crowded and he’s gone for a while. I ignore the texts from G, who is hoping to have an encore. I delete his number and get the feeling a mature, worldly guy like J could be a fun conquest. I turn my head, glad to see him headed back with two martinis in hand.
8:30 p.m. I have fun maintaining an innocent flirtation. He is tall, dark, and handsome and seems warm, considerate, and interesting. I love the butterflies I am feeling right now; it has been a long time!
10 p.m. He offers to show me his new luxury apartment in Dumbo. I coyly turn him down because I need to be up early. As soon as the words come out of my mouth, I feel slightly regretful and suddenly notice he has ridiculously plump lips. I think this is the right move for tonight.
DAY FOUR
7 a.m. I haven’t heard from A in months, so I’m surprised when he texts asking if I want to go to a Bad Religion show. I wonder if he heard J moved back. We are still concert buddies from time to time, but he reaches out more than I would like considering he recently got married. During an ugly fight once, he accused me of “wanting to sleep with everybody.” I have started to wonder if that’s true.
2 p.m. I have a few life-coaching clients to handle, back-to-back.
5 p.m. Zooming has totally exhausted me. I eat some leftover takeout and plop myself on the couch.
5:45 p.m. J texts to say he happens to be driving past my house; do I want to meet up? The timing couldn’t be better. I am so ready to get out! I had no time to research, so I suggest a nearby cocktail bar, an old Italian social club he hasn’t been to since he’s been back.
9 p.m. After two cocktails, I know I will be in bad shape and mention I should grab a car home. Despite being out of his way, he offers me the ride and I’m happy to spend a few more minutes with him. We pull up to my place and before I know it, we are making out and I am enjoying every second of sucking on his luscious lips. He knows just the right way to catch my tongue so that it sends tingles all the way down my body. As we make out in that Uber, all I can imagine is him sliding his hands down my pants.
I feel the blood rushing and don’t want him to know how easily I can orgasm. Sometimes it makes me feel embarrassed, like a teenage boy who prematurely ejaculates. Of course, I am grateful for multiple orgasms. We pull apart and both look at each other with that awkward “I kind of want to eat you up right now, but I’m going to play it cool” look. I give him my best puppy eyes, take a deep breath, and let him know I should get going. As I key into my building I glance back; he didn’t drive away without that final wave.
9:15 p.m. I can barely make it up the elevator to my apartment. I go right into bed and touch myself.
DAY FIVE
10 a.m. I wake up in a much better mood than I have in a while. The potential of hooking up with J has my mind racing.
3:30 p.m. Work is dragging and now I’m antsy. Virtual sessions have been boring, but I have yet to secure a place for in-person sessions since many of my clients still prefer meeting online.
6 p.m. I had movie plans with a friend who is notoriously unreliable and cancels at the last minute. I tell J I have tickets to the latest Marvel film. His ex is a filmmaker, so he is very knowledgeable about movies and up on celebrity lifestyles. I feel self-conscious about my lowbrow movie taste, but figure everyone likes an action flick.
7 p.m. We grab Shake Shack and meet up with a Swedish model friend I met at a party a few months ago. She brought hash (not to be confused with weed), which I have never tried. We get so high I barely understand the premise of the film but enjoy it nonetheless.
9:30 p.m. I am off tomorrow, so when J mentions his place again, I accept. His apartment has a sick view and is full of things I am afraid to touch. I ask if we can smoke some hash so I can ease some nerves. When we come in from the balcony, it feels like seconds before our hands are all over each other. Before I know it we are on our sides 69ing; he tells me it’s his favorite position. It turns out he has also played around with some tantra so we make it last a while. We both orgasm and slowly fall asleep.
DAY SEVEN
8 a.m. We wake up relaxed and ready to go again. He takes such care with every part of my body, and seeing his lips around my nipples is enough to get me off. I can be shy in bed with a stranger, but he automatically puts me at ease. I ask if I can sit on his face (a question I luckily have yet to hear “no” to). It is my favorite position. As a petite woman, I have always felt a sense of control in the bedroom when I can come on a man’s face.
9 a.m. We are still going. I’m psyched it’s the weekend and we can take as much time as we need.
12 p.m. We head to brunch and as usual, conversation flows easily. He talks a lot about his ex and how the sex was very emotionally intense, but he has no regrets. Turns out he doesn’t date men much these days and is very clear about not wanting to be held down by anybody as he starts his newly single life. As excited as I am by our little dalliance, this is a relief. I was a serial monogamist for years and want to get my coaching business established before seriously dating again.
2:30 p.m. I am home and exhausted.
8 p.m. I remember what he said about bringing home men to have sex with him and his ex-wife, and wonder if he would ever want to do that with me. That’s always been a fantasy of mine. I try not to get too excited and strategize finagling that into the next conversation! A woman can dream …
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