This week, a woman has fun with several flings, including a sketchy dad and a preppy banker: 31, single, Austin.
DAY ONE
8 a.m. I got home late last night from a weekend in Houston. I was there to hook up with a guy, Jeff, who I met at a wedding a few weeks ago. The trip didn’t go as planned. He totally flaked on me, claiming to be sick. Like, I was literally at a bar waiting for him, in sexy underwear, and he sent a text saying, “I’m so dizzy; I’m so sick; I need to procure a thermometer.” Who says procure? I was like, “Um, feel better?”
By the way, I’m a recently divorced consultant having a lot of casual sex. Generally I’m loving it, but this situation set me back a bit!
9 a.m. Monday morning. I have work (from home today). Before starting, I blast Olivia Rodrigo and make a breakfast sandwich. Then, the meetings begin. My focus is financial consulting.
1 p.m. I step out to grab lunch from a local food truck and call my best friend to debrief her on Jeff. He was totally my type. Tall with longish hair — artsy and edgy. At the wedding, he tried to convince me to have a threesome with another woman. She wasn’t into it, but I did have sex with him that night. It was good enough that I visited him again. I’m so pissed he flaked!
6 p.m. Dealing with some paperwork for my divorce. The sex was great, but over the last few years, the relationship just stopped being fun. We got married young and being a traditional wife in Texas was not working for me. Like, I was on the board at a country club.
Anyway, we don’t have kids, so the divorce mostly feels like a bad breakup. It’s strange, though. He’s in our big house with our dog, while I’m in a rental in the best part of the city, going out every night and having a good time.
9 p.m. Scrolling Instagram, and I see that Jeff is literally in the hospital. He has pneumonia and, apparently, terrible asthma. I can’t believe it wasn’t a lie. Now I feel really bad. I think back to our night of sex … I was on top the whole time and I do kind of remember him wheezing. I text him that I’m praying for his good health!
DAY TWO
10 a.m. I text a guy, Max, who I dated five years ago, about hanging out tonight. He’s a preppy banker type who is surprisingly good at sex. He says he’s totally free and would love to reconnect.
11 a.m. Spend the morning making decks and presentations.
1 p.m. Sneak away from my computer and work out at the gym I just joined. I feel the urge to flirt, but everyone at the gym is gay. Damn!
3 p.m. Jeff writes me back. He’s home and recovering. I send something flirty back, and we start texting nonstop. He may be sick, but his banter is great.
6 p.m. Max picks me up to take me to drinks, then dinner. We always have a great time together. On our first couple of dates all those years ago he took me to the Caymans. He’s that type of guy.
11 p.m. Night with Max ends with a little makeout session in his car, but I’m not really feeling it. When I’m back, I text another guy, Logan, about coming over, but I fall asleep before he responds. I met Logan at a party while I was still married. We flirted a ton, but I was faithful the whole time I was with my ex.
DAY THREE
9 a.m. Wake up to another text from Jeff. We’ve been texting for like 24 hours. He’s up to date on all my dates. I’m keeping up with his recovery. I’m really starting to like this guy!
1 p.m. Another day of work Zooms. A clients’ stock price is down, so they’re yelling at me. Great.
3 p.m. Jeff sends me a dick pic. It’s his dick in his hand and nearby there’s a remote. I guess for scale? It was unprovoked. I immediately send it to all of my friends.
6 p.m. I go to this charity board meeting. A friend of mine wants to set me up with one of her friends, Jake. He has kids, but that’s okay.
She connects us via text and we decide to meet up tomorrow. I tell him I have dinner with my girlfriends, but we can meet before or after.
DAY FOUR
10 a.m. Have a coffee meeting with a colleague-friend from work. He’s older and loves hearing about my newly single life. I tell him everything. I’m not afraid to be myself!
1 p.m. Jake texts to solidify our plans for tonight. We decide to meet for happy hour before I see my girls.
4 p.m. At home, I shower and put on a pair of sexy underwear.
6 p.m. Jake is a little nerdier than my usual type. We both work in consulting, so it’s nice to bond over work, but I’m not sure about him otherwise. He tells me he has two very young children. One is literally a baby. The math doesn’t really add up. He says he’s been separated for over a year … but the baby is barely a year old? He also tells me about an affair he had while he was married. Overall, it’s messy. I’m thinking, like, maybe don’t lead with all this on a first date?
7:30 p.m. We go into his car to make out. While we’re kissing, I notice the kids’ car seats in the back. It kind of turns me off. I hastily order an Uber to head to my dinner.
10 p.m. Great dinner with my girls. We decide to go dancing at this old-school club in the area. I text Jake that he can come if he brings me a phone charger. So he shows up an hour later with a phone charger and some acid. Okay!
11:30 p.m. Jake is dancing with my friends and we’re all doing a little acid. It’s super fun. I decide I’m attracted to him, but maybe it’s just the acid.
1 a.m. I head home, but Jake and I text until I fall asleep.
DAY FIVE
10 a.m. Jake has been texting me all morning. He sends me a good-morning video while driving. I write back, “Don’t use your phone while driving!” Also, you can see a 3-year-old in the back and hear a baby crying! Ugh, it’s the worst video on the planet. I send it to all of my friends.
1 p.m. My friends are dying at the chaotic video. Jake is fun but seems to be a mess. Like noooo. Just no.
5 p.m. Meet up with my brother and our mutual friends for happy hour. Jake is really pushing for me to come over later.
10 p.m. Jake texts, “Please come over … I’ll make you a fire and a drink and we can talk about your divorce.” My friends are tired of hearing about my divorce, so I’m tempted.
11 p.m. I Uber to Jake’s. His place screams “divorced dad.” It’s a sad furnished rental with zero female energy. And the fire he’s going to light me? It’s one of those portable stove things, not a beautiful fireplace. It’s so depressing I drink a whole bottle of wine.
1 a.m. We go upstairs. I’m wearing the hot underwear. He’s loving it. We’re about to have sex when I hear the baby crying. It kind of kills the mood, but then the baby stops and falls asleep. We have sex, it’s not bad, and we fall asleep.
DAY SIX
8 a.m. I wake up because Jake’s toddler is in the room tugging him awake. We head downstairs. Jake needs to feed the kids. He asks me to hold the baby. I’m annoyed. Like, I have to go home! I have things going on! I shouldn’t be looking after your kids!
9 a.m. Back at my place. Jake is already texting me. I’m not that responsive. He says he’s flying to Vegas later today. Nothing about any of this is sexy.
12 p.m. Jake is still texting. Men are so annoying. I decide to take the night off from them and go to the movies by myself later. I need a quiet night with no drinking.
4 p.m. Jake sends a picture of his feet in a pedicure bath in Vegas. I’m like, gross. I can tell he’s offended by my attitude, and that we won’t be seeing each other again. That’s totally fine.
5 p.m. On the way to the movies, I stop at my favorite bar for a martini. I sit alone and have a drink. I can’t help myself and text Logan. He swings on over.
6 p.m. We’re having fun. I decide to skip the movie. He says he’s seeing someone but it’s nothing serious.
8 p.m. We end up getting drunk and heading to his place to have sex. It’s not bad. Not very impressive in the equipment department, but I kind of enjoy myself!
10 p.m. On my way out, I tell him that I’m going to a cookie swap in the morning. He’s super weird about it. I have no idea why.
11 p.m. I call one of my friends on the ride home and mention the cookie-swap awkwardness. She explains that Logan has a serious girlfriend who will definitely be at the cookie swap tomorrow. Apparently they’ve been together for months. WTF!
DAY SEVEN
10 a.m. At the cookie swap. I keep to myself. I don’t want the drama. I’m not even curious which one the girlfriend is.
12 p.m. Driving home, thinking about all the men I’ve been with since my divorce. They’re all fun and distraction. I’m enjoying myself, but it’s also kind of tiring!
3 p.m. Damn, I’m tired. I’ve been going out a lot. I decide to order Thai food tonight and watch a movie at home.
6 p.m. While eating my Thai, I randomly get a text from a guy who I’ve worked on a couple projects with in the past. He lives in San Francisco. We always had intense chemistry, and we start texting a ton. It turns out he’s also single, which he wasn’t in the past. I can’t believe my luck. We’re texting and flirting, and before long there’s a flight from Austin to SF in my inbox.
8 p.m. I feel floaty for the rest of the evening. I have this crazy feeling that I’m about to fall in love with this man. I can’t stop smiling.
10 p.m. Pack for San Francisco, and head to bed.
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