Here we are again with another awkward sexual encounter from the U Up? Podcast. These stories written to Jared and Jordana will definitely make yourself feel better about your whole life’s worth of embarrassing moments. Sorry not sorry to those actually experiencing them. Let’s dive in to this week’s letter.
Hi Jared and Jordana,
Happy pre-cuffing season. A few nights ago I went out with a guy who was 10/10 hot, and apparently rich (the dream).
Lol. Pre-cuffing season. For those of you who don’t know, cuffing season is the time between Thanksgiving and Valentine’s Day to “cuff” or tie someone down for the holiday season. Because you know, the holidays and winter make you want someone to cuddle up with, naturally.
I go back to his apartment (studio on the UES), and things unfold as they usually do. I have an alarm set so I can go back home in the morning and get ready for work.
Of course, as one does.
When I go to leave his apartment around 6am, I open the front door, the tenant across the hall also opens the door and calls his name (also Jared lol). Clearly, I am not Jared. After she realizes this she retreats awkwardly back into her unit without saying anything.
Okay, weird. Immediately I’m thinking as the reader that this is another bitch he’s been seeing, but you went out with the guy once, so chill.
A few hours later I text the guy and mention it and he brushes it off. I go to his place again last night, and he says he has to go into the unit across the hall since the other person moved out and he has to take care of some things???
What kind of things?? Idgi.
I thought it was a bit odd that he didn’t say anything about the woman who asked for him the other morning, and now we’re in her apartment, so I asked again. Turns out his family owns the whole building and that was his MOM.
Anyway, please let me know what you’d call this one.
Xoxo, Meeting the family Betch
THAT took a turn. Was not expecting that one. NGL, if I was in that situation I would run. A “Momma’s Boy” is one of the biggest turnoffs to me. This gives me Failure to Launch vibes. I mean, at least this guy doesn’t live at home with his parents. But, the fact that his mother lives down the hall is bad enough for me. I don’t care how hot or how rich he is. Run, sister, run.
To hear Jared and Jordana’s take on this story, listen to U Up? below.
Images: Timur Romanov / Unsplash
