Another week, another hookup horror story. This week’s latest awkward sex from U Up? will definitely make you feel better about your own hookups and relationships—yeah, it’s that insane. Let’s dive in.
Hey J and J,
Love the podcast! It makes me feel I have a superpower for understanding the male mind. All my friends totally love all of the unsolicited advice I give them about their love lives now.
I know y’all have gotten a few sleep talking awkward sex moments but this one was way more than talking. I have a once-or-twice-a-year booty call thing with a guy I dated for 2-3 months a couple of years ago. Last night he came over and after hooking up, he fell asleep immediately (Like every guy).
Like. Every. Guy. Lol. No after sex spoon sesh? Not even a kiss goodnight?
I knew from our previous hook ups that he has some really weird sleep habits – twitching, flaying his arms, sleep talking etc – and so I was having a hard time sleeping next to him.
Brennan? Dale? Is that you?
In the middle of the night, he rolled over and was like “I want you to sit on my face right now.” I said “what?” And he said it again and kind of pulled me up on top of him and he started going for it. I was up there for a minute or so but something was just a little weird and I was like what the fuck it’s 4 am I’m going to sleep. So, I … um… dismounted and he immediately did the twitching thing that he does in his sleep.
This may be the funniest part of this whole situation. Not the fact that in his sleep he wants her to sit on his face, but the fact that she didn’t realize it was weird until after the fact.
I thought he had just fallen back asleep really fast. A few mins later he rolled over so that we were spooning and he started talking about how he wanted to have sex with me. He was kind of trying to but not really, so I started to think he was sleep talking. I told him that I wanted to go to sleep (obviously I have moral qualms about having sex with someone who is asleep even if they are asking for it haha) and he rolled back over.
Is it that obvious? I mean you sat on his face a few minutes ago??
Then – for his grand finale- he turns to me and goes “hey I love you and I’m sorry about Saturday.” I looked at him like he was crazy and he grabbed my face and repeated it again: “I LOVE you and I’m so sorry about Saturday!” He 100% does not love me so that was definitely confirmation that he was still asleep. Who knows who he was actually dreaming about!
I love how she calls this the “grand finale.” I find that hilarious. At this point in the night, I would be laughing so hard I would wake him up and tell him about all the weird sh*t he’s put me through that night, then have him call me an Uber home.
I asked him in the morning if he remembered the middle of the night romp and he had no clue what I was talking about so I think he was asleep for the whole thing. Maybe he has sex insomnia which I’m pretty sure I heard once about on Law & Order: SVU? Obviously I didn’t tell him that he told me he loved me because I knew he’d think I was fully insane. I can’t believe he could literally eat me out in his sleep, but the “I love you” thing makes me sure he was out cold.
I WISH this girl asked him questions the next day, or at least told him everything that happened.
Hope this makes y’all laugh! I’d love to know if you think this is even possible!
Also the phrase “wake up sleepy pussy” was involved somehow? 🥴🤢
What would you call this?
The Night Rider? Dream Girl? Night of the Living Head?
I actually laughed out loud to this letter. If someone ever said these things to me in their sleep, I would be concerned and uncomfy…100% a deal-breaker for me.
Find out what Jordana and Jared thinks about this on the latest episode of the U Up? podcast.
Images: Adi Goldstein / Unsplash
Welcome again to this week’s U Up Podcast’s Hookup Horror Story, where making fun of people and laughing at their embarrassing hookups are required. Here’s another listener-submitted awkward sexual encounter for your pleasure. Let’s break it down.
Hey J & J,
Coming in hot with an awkward story and an important question about acceptable, shall we say, TERMINOLOGY in the bedroom.
I’m a single gal in her late 20s, finding myself balls-deep in friends’ weddings lately.
Balls-deep… literally, as we’ll soon see.
Recently I ended up going home after a great wedding and perhaps too many great drinks with guy 5ish years younger than me. All good, no problem there.
Sometimes when you’re single at a wedding, you have to rob the cradle.
But you know when you’re borderline blacked out and then something happens that instantly snaps you into a brief moment of sobriety?
Don’t we all.
Well, we were hooking up and everything was going great however he was talking A LOT. I’m not even sure what he was talking about but I just remember thinking, “wow he is chatty.” It was truly distracting.
That’s the worst. I’m not even sure you can call it “going great” if he was talking the whole time. Kinda kills the mood.
And THEN… he starts enthusiastically repeating over and over, “I wanna make you nut.” I literally laughed out loud the first time he said it. He was not trying to be funny. This was serious. I’ve never heard any dude say NUT in reference to a female orgasm. It was unreal. So, what do you guys think?? Is NUTTING in the lexicon of acceptable dirty talk?
P.s. I nutted
HAHAHA what!!?? I’m actually uncomfortable. I don’t know how she “nutted” after that, because I’d be done.
Can women “nut” (god, just typing that is making me cringe). Listen to Jared and Jordana discuss on the latest episode of U Up?
What do you think? Does this track? Or is it a no? Let us know in the comments!
Image: Maddi Bazzocco / Unsplash
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
Another week. Another hookup horror story. Hookup culture, for all of its pitfalls, makes up for it by providing hilarious meet-not-cutes like no other cultural phenomenon can. This is especially true for collegiate hookup culture. Something about the sultry mix of frat-level hubris and a sh*t ton of alcohol makes for a cocktail rich in awkward encounters and cringey moments. U Up’s latest awkward sexual encounter is a testament to this, and we broke it down for you.
Dear J&J, Thanks for doing the Lord’s work, I’ve shared the podcast with all my friends and am bringing a huge crowd to your live show in Dallas. A few months ago I had a hilarious sexual experience and thought I should share. I had been hooking up on and off with this guy throughout college—just sex, as I knew he was slightly unhinged.
I’m sorry, unhinged?? I understand making an exception in the name of getting laid. He talks too much? Step up the tongue action. He has a lazy eye? Keep your eyes shut. But if your list of potential “exceptions” includes f*cking the occasional psychopath, I think it’s time to reevaluate your hookup standards.
My senior year I lived in the sorority house and had it on the bucket list to sneak a guy in. I invited him over and he showed up very drunk while I was sober. We start hooking up and I asked if he had a condom and he said no so I told him we couldn’t have sex.
Stay safe, kiddos.
He started freaking out and screaming “f*ck f*ck f*ck” so loud i was worried he was going to wake the house mother.
If the house mother is only a feature in your awkward hookup, and not the main event, you know you’ve got one hell of a story. Greek life is one of those strange institutions that manages to supply you with lots of booze and raunch during your university days, while also making you feel like a high schooler, only with a Mom who is extremely strict and culturally stuck in the 1940s.
To calm him down I told him we could hook up another night this week. He then told me that he was going to “f*ck me until the cows come home” and make me “come so hard he would kill me” he then kept repeating that, saying “I’m gonna kill you Sunday” “I’m gonna kill you Sunday.”
Alright, this guy must be Bachelor-level hot. Nothing makes the entitlement of frat guys clearer when it comes to sex like extremely weird dirty talk and low-key murder threats. Either this guy is a lit major who got a little overzealous with the word play, or lines like this have worked in the past. If it is the former, he clearly needs to work on his transitions, as cows and homicide don’t exactly pair well together. If it is the latter, it is time for us betches to band together and makes sure this behavior does not go rewarded in the future.
He then asked me if we could do “crazy kinky shit” even if we couldn’t have sex and asked me repeatedly to have anal, which we’ve never done.
You do not mention cows in one sentence, then f*cking me in the ass in the next. No. Absolutely not.
I drove him home after that so that I could get him out of the house before he caused more of a scene. In the car, he started trying to finger me while driving and said “i could totally make you crash this car right now” and when I pushed him away he started screaming “f*ck f*ck f*ck” and banging his head against my dashboard so hard I thought he might deploy the airbags.
Well, at the very least he’s consistent. That said, he really needs to reevaluate his standards if crashing a car is somehow a sexual victory. If his affinity for weird pickup lines doesn’t keep him from getting laid in the future, hopefully the massive bruise on his head after BANGING IT ON THE WINDOW (?!?!) will.
I finally got him out of the car and had a story for the ages. Let me know what you would call this!
While part of me (most of me) thinks you should really elevate your standards (aka stop f*cking Crazy Chad), the other part of me is grateful for your service. If this girl is willing to satisfy the sexual cravings of the world’s crazies, I’d say she’s the one doing the Lord’s work here.
How do you feel about banging the occasional crazy? Hear Jared and Jordana’s thoughts on the U Up? podcast below.
If you love laughing at other people’s embarrassing stories and misery, you’ve come to the right place. Jared and Jordana blessed us with another listener-submitted awkward sexual encounter story on the U Up? podcast, so we of course have to break it down for you.
“Hi Jared & Jordana! Background info: I recently moved home after a career change and my new-at-the-time boyfriend also moved home after he got out of the military. Both of our mothers are teachers, so it’s rare that either of us get any ~sexy time~ in the summer since someone is always home.”
This situation is already awkward because it feels like these two have reverted back to a high school relationship. Good for them for making it work under the circumstances. I’d feel on edge knowing my mom (or his!) could walk in at any moment and put me in such an uncomfortable situation that I would have to change my identity and move away.
“I was driving home from work one night when he booty called me, so I drove to his house and told my family that I was stuck at work. We got hot & heavy REAL fast, and ended up having sex on his living room floor (the rug burn was worth it).”
I’m sorry, when is rug burn ever worth it? Just do it on the bed like normal people. Maybe I’m just jealous of the youthful vitality that would possess someone to think having sex on the floor is a good idea (can you say knee pain?), or maybe I’m a buzzkill. However boring I may be, I know for a fact that at the end of the day the person who has sex on their bed will be able to then sleep in said bed with much more peace and comfort sans rug burns and bruised knee caps.
“He decided he wanted to cum in my mouth, but wasn’t fast enough; most of the jizz ended up on my face.”
This sentence is just a lot to take in. I feel like this is the kind of sentence my freshman English professor would pick apart mercilessly make us study for an entire class. If you separate it into different lines it could literally be a Rupi Kaur poem. Wow.
“At first this wasn’t an issue, just towel off, right? Wrong. His cum got in one of my eyes, and it immediately turned bloodshot because I wear contacts. I ran to the bathroom to take my contact lens out and flush my eye with water, but it only got worse and started burning.”
This is just the worst. There is no bigger feeling of defeat than when you’ve done something to f*ck up your delicate little eyeball and literally nothing you do to try to fix it makes it feel better. And then the pain is so bad that you start crying and your poor eye starts doing even more work.
“I ended up driving home while holding a wet paper towel over the eye and told my family something got in my eye at work.”
This poor girl can’t catch a break. Her boyfriend gets cum in her eye and then she can’t even go home and bitch about it to whoever will listen. She just has to suffer in silence. What a strong woman. I have so much respect for her, but I do not envy her.
“Anyway, would love to hear what name you give this! I’ll hopefully be seeing you at your Philly show.
What would you call this situation? Would you forgive your boyfriend for this very unfortunate slip-up? Honestly, at least it wasn’t any of their parents walking in on them. To hear what Jared and Jordana thought, listen to U Up? below.
Images: HBO; Tenor (2)
If you enjoyed the story of the girl who lost her tampon in her vagina as told by Jared and Jordana on the U Up? podcast, you’re in luck because here we are again with another awkward sexual encounter to make you feel better about the embarrassing sh*t you gotten yourself into this past weekend. This week, we tell the tale of a girl who found a tick on her hookup in the middle of the deed.
“Hey J&J! I’ve been seeing a girl from the south and she recently took a trip up to visit me in New Jersey,” she writes.
I wonder what a southern belle’s first impression of New Jersey, the so-called armpit of the United States, was. When I hear “girl from the south” I automatically think of a very blonde, very tan, very proper girl who says things like “y’all” and “Roll Tide.” I just realized I’m describing our latest Bachelorette, but that’s neither here nor there. Anyway, this girl must be really into this person if she jumped at the opportunity to travel to the land of Snooki and Teresa Giudice.
“We spent the afternoon in a botanical garden, having a picnic and rolling around in the grass and such—becoming one with nature, so to speak.”
I didn’t know botanical gardens even had areas private enough to lend themselves to such “rolling around,” but kudos to them for making it work.
“Later that night we were hooking up and as I whipped out our brand new sex toy to penetrate her (P.S. I’m a girl) I felt a bump on her hip. I look down and find a tick attached to her.”
I wonder if it took any amount of time or contemplation for her to determine whether this bump was just a mole or an actual bug burrowed into this girl’s skin. Imagine it was just a mole and she made a big deal out of inspecting this bump? That might have been an even worse story than this one.
“She began freaking out as ticks aren’t something you encounter much in the south.”
Uhh, yeah, no sh*t she was freaking out. Being scared of a tick isn’t really a cultural difference that exists between northerners and southerners. Maybe she’s seen a season or two of Real Housewives of Beverly Hills and knows that a tick can give you Lyme disease. It would’ve been weirder if she didn’t freak out. I, for one, do not trust anyone who wouldn’t scream at the sight of a bug sticking out of their skin.
“I ran naked to wake up my roommate in medical school to assess the situation but she was no help.”
What kind of relationship do these roommates have that she feels okay running into her room and waking her up while she’s unclothed? Can you imagine being deep into a blissful slumber when your roommate flings your door open and runs up to your bed stark naked while screaming about a tick? I’d be moving out the next day.
“After some googling we discovered since the tick was only on for a few hours so she’s probably fine, but I most definitely scared her off dear sweet NJ. Hope this gets a laugh!”
As if New Jersey didn’t have a negative enough connotation for the southern girl to begin with, she now associates it with the time she got a tick and narrowly avoided contracting Lyme disease. I feel sorry for the girl who brought her there and wish her the best of luck in continuing that relationship.
What would you do if you brought your hookup to the place where they’d get a tick? Or worse, what would you do if you were the one that got the tick? I feel like I’d honestly be too traumatized to ever speak to the other person again. But I am pretty dramatic and have a crippling fear of bugs, so idk.
To hear Jared and Jordana’s take on this story, listen to U Up? below.
Images: Hector Gomez / Unsplash; Tenor (2); Giphy (2)