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.
Much love,
Pirate girl”
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)
The U Up? podcast is heading out on a 20-city national tour this month, and just announced, U Up? Live is also a headliner at this November’s New York Comedy Festival. Yeah, it’s a big f*cking deal. U Up? Live is on Friday, November 8th at the Town Hall, and general admission and VIP tickets are on sale now. Other headliners for this year’s 16th Annual NYCF include Stephen Colbert, Trevor Noah, and Nicole Byer, and overall, the festival consists of more than 200 amazing acts at over 100 venues across the city. So basically, you’ll have major FOMO if you don’t go, and there’s really no excuse for missing out.
Cohosts Jordana Abraham and Jared Freid always bring the dating expertise on the U Up? podcast, and their live shows are no different. Whether you and your friends are in desperate need of some help in your dating lives, or you just want to have a good time with Jordana and Jared, you definitely need to buy your tickets to U Up? Live ASAP. Thousands of people have already had the amazing experience of playing Red Flag or Deal Breaker live, and you’re next.
Click here to get all the information and buy your tickets to U Up? Live at the New York Comedy Festival, and if you can’t make it to the show in NYC (I said no excuses, but whatever), here’s all the info about the other 20 shows J&J are doing this fall. They’re probably coming to a city near you, so actually like, no excuses.
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)
As much as we all like to think of ourselves as empathetic beings who don’t get enjoyment out of people’s misery, we all love to cringe (and laugh) at a good embarrassing sex story. It’s fun to hear about the horrible things people have been traumatized by in bed, as long as we’re not the ones undergoing the traumatizing. That’s why this crazy story Jared and Jordana chose as the “Awkward Sexual Encounter” of the week that on the U Up? podcast that a fan sent in is so horribly entertaining. And before you come swinging with your “ThIs DeFiNiTeLy DiDn’T hApPeN!!1!1” comments, homegirl sent us a picture of her literal receipt for proof (but more on that later).
The listener wrote, “So yesterday was a major annual parade in my city – everyone day drinks for it and goes out to bars afterwards. After many hours of drinking and a few too many vodka sodas, I met a guy in a bar and we hit it off. My memory of the entire night is fuzzy at best, but we went home together. I woke up the next morning needing to pee and to get some water. As I was peeing, I realized I had gotten my period the day before but had no memory of taking my tampon out. I reached down to feel for the string but couldn’t find it.”
Oh no. Imagine the panicked thoughts running through this poor girl’s head at this point. Sunday scaries at their STRONGEST. Was the tampon totally gone? Did she not realize she had been free bleeding all night? Then she figured out what actually happened, which was even worse.
“Terror began to set in. Upon further investigation, I found the tampon lodged deep in my vagina. I knew that we hadn’t had sex but he had fingered me A LOT. Apparently in the process, he had shoved my tampon so far up that I couldn’t get it out. This is literally the type of horror story you hear about in middle school Sex Ed.
“I got back into bed with him and felt like I needed to tell him in case I died of sepsis on the spot. He was a great sport – clearly had not felt the tampon at any point the night before and felt badly about it but we were able to joke about it. Anyway, after a lot of googling for tips and tricks and a few hours of fishing around, I gave up and went to Urgent Care.”
Can you imagine the horrifying moment of accepting defeat, swallowing any pride you had left, and surrendering your vagina to a medical professional to remove the tampon stuck so far up it? I just shuddered.
II think basically the entire staff was behind the front desk when they asked me what I needed help with. I’m free of the “foreign body” but have to use pads this week because my poor vagina took such a beating.”
To spare this girl of any more embarrassment after having gone through all of this and then sending it to us to share with the whole world, I won’t attach the picture of her urgent care outpatient form. But I will tell you that it actually has the words “The following issue was addressed: foreign body in vagina” on it. Next time you wake up the morning after a hookup and feel bad about not remembering much from the night before, be grateful that you don’t have a tampon wedged so far up your vagina that you have to have a doctor remove it.
To hear more from Jared and Jordana on this unfortunate story, listen to U Up? below.
Images: Kinga Cichewicz / Unsplash; Tenor (2); Giphy (2)
Giving the perfect speech at a wedding is like making a joke on Twitter in 2019: it’s difficult to think of something that reads as funny and original to everyone AND doesn’t offend anyone at all. You have to balance joking with being sentimental, make sure what you’re saying fits the whole couple and not just the partner you’re closest with, and please the bride/groom while pleasing the entire crowd as well. Your friend may think the story about the bride blacking out on spring break in Cancun sophomore year is hysterical, but the bride’s grandmother probably won’t. On top of all of this, a room full of both strangers and familiar (but not necessarily friendly) faces is listening to you. On the latest episode of the U Up? podcast, Jared and Jordana broke down the dos and don’ts of giving a great wedding speech that will make everyone ask YOU for help writing their speeches for the next wedding.
1. Don’t Speak As A Group
As a bridesmaid or groomsman, having others up there by your side seems like it would make the speaking process way easier and more comfortable, which would in turn makes for a more effortless-sounding speech. But it actually ends up making everything sound way less cohesive and even more awkward. Jared points out, “Every time you switch people, you lose momentum. We don’t even get used to the tone of the speech because it changes seven times.” A few drinks in, people won’t be able to keep up with the changes. Just as they all get warmed up to the person speaking, you move onto someone new and they’re left to readjust all over again. Your part will just blend in with the crowd. You don’t want your best friend’s annoying college roommate to taint the entire speech because of how terrible her part is, or worse, dull the effect of your part. Step off, Emily, she’s been my best friend since KINDERGARTEN.
2. Don’t Make It Too Personal
It feels nice to give the bride/groom a speech that is very specific to them and include inside jokes that make you feel special, but when you’re speaking in front of a whole audience, you need to keep them in mind. Whoever’s listening wants to feel like they’re in on the joke too, or else they won’t think it’s funny. Avoid the “had to be there” stories and stick to making references about the bride/groom’s personality that everyone in the room will understand and identify with, because that will get a reaction from the most people. If the bride is notoriously obsessed with her dog, write about the time she brought Fluffy to brunch and you guys got kicked out because she peed on the floor. (The dog, not the bride.)
3. Don’t Be Too Self-Important
It obviously makes sense for you to introduce yourself when starting your speech, but people don’t need to know every detail about who you are, how you met the bride/groom, what you do for a living, how far you traveled to get there, and what you ate for dinner last night. Everyone’s there to celebrate the couple getting married, not the weirdo who cares way too much about everyone knowing exactly who she is. Chill, dude. I know you want every groomsman to know you’re single, but there’s this thing called introducing yourself (which you can do later). Get the speech moving and keep the focus on the people the wedding is actually for.
4. Tell That “One Great Story” You’ve Told A Thousand Times
Everyone thinks it’s better to be original than repeat a story you’ve already told, especially because people get called out for telling the same story over and over again and you want to do something unique for this special occasion, but there’s obviously a reason you associate this one story with the person so strongly and have continued to tell it time and time again. Since you already know it backwards and forwards, you are able to determine what parts work people think are funny and build on those instead of using material that may or may not land.
5. Don’t Use Generic Jokes You Found By Googling “Wedding Speech Jokes”
As Jared pointed out, everyone has heard the line “Thank you for making me your best man, I hope I can be the best man at your next wedding, too” before, Not only is it not funny, it’s sooo cringeworthy. Whoever thought joking about how long the relationship will last at a couple’s literal WEDDING was a good idea? Using that line is a good way to make everyone feel uncomfortable and judge you. Just don’t be that guy.
6. Bring It Back To The Couple
No matter what you say, you always want to find a way to tie it back to how perfect the bride and groom are for each other. However funny or incredible your speech is, it’s not going to hit home with everyone unless it somehow connects both people getting married. How great the couple is together is something that every wedding guest can get behind (at least I would hope). Save the love fest for just your best friend until her birthday, when you know everyone is there for her and only her.
7. Don’t Overstay Your Welcome
Even an impeccable speech has a time limit. Everyone can only pay attention for so long, and especially if there are more people up after you, you have to be quick. Get in, say what you gotta say, and then GTFO of there. Short didn’t become associated with sweet for nothing!
For more of Jared and Jordana’s expert opinions on how to give the best wedding speech, listen to U Up? below.
Images: Alasdair Elmes / Unsplash; Giphy (2); Tenor (5)
It feels like there is never a correct answer for what you should do when you don’t like your friend’s significant other. You don’t want to meddle in matters that don’t really concern you or ruin the way they view someone they actually like a lot, but you also feel responsible for looking out for them if you genuinely feel like they’re getting involved with a piece of sh*t. So how are you supposed to know which approach to take? Luckily for you, Jared and Jordana broke down their tips for how to go about this sort of tricky situation in the latest episode of the U Up? Podcast. Here are some tips for what to do, and what not to do, when you’re not a fan of the person your friend is dating.
1. Consider Whether You Don’t Like Them In General Or As A Partner
How serious is the level of dislike? Is it just that you don’t vibe with the way they consistently tell knock-knock jokes, or does your friend really value a good sense of humor and self-awareness and you’re not sure if this is the person for them? There’s a difference. If you genuinely think your friend’s judgement has been clouded on who they’ve decided to associate with and feel like the person isn’t a match for your friend’s personality and preferences, then it might be worth bringing something up. But if the person just rubs you the wrong way personally and isn’t a total asshole, it’d probably be selfish of you to say anything.
2. Tell Them From The Start Or Don’t Tell Them At All
It’s way easier to voice your unfavorable opinions when the relationship is still very new and they haven’t caught very strong feelings yet. Jordana thinks it’s better to just say it “when there are no stakes, and if your friend doesn’t care, it’s fine.” This way, you get it off your chest quickly and you don’t have to worry about your friend asking why you didn’t tell them sooner. If they still date the person after you speak your mind, then you just accept it and move on.
3. Only Present Facts, Not Vague Opinions
If you do decide to take the plunge and tell your friend, it’s more effective (and makes you look like less of an asshole) if you have specific incidents to back up your claim. Instead of just expressing general dislike that could come across as unwarranted, Jordana thinks it’s better to say “This thing happened. I felt a little weird about it.” For instance, instead of just claiming the person seems unnecessarily aggressive, describe how you didn’t like the time they lost their sh*t when your friend packed SPF 50 instead of SPF 30 on the day you all went to the beach. Basically, bring the receipts.
4. Only Give Advice When It’s Asked For
Jared thinks it’s best to hold off on giving unwarranted opinions about your friend’s serious significant other at all, and wait until your friend comes to you asking specifically for your thoughts. In an instance where he knew his friends weren’t too fond of his girlfriend at the time, he asked them, “What do you think?” They then asked him, “Well what do you think?” which let him know there was something wrong but also allowed him to talk about how he was feeling and explore his own thoughts. Being sensitive to and aware of your friend’s own mindset is what someone who truly cares would do.
5. Go With The Flow Of Changing Social Circles
If your friend is not someone you’re so close with that not seeing them as frequently would be a huge loss, then it might make sense to drift apart if you really can’t stand the person they’re dating. Jared said, “Your social circle changes when you become a couple. You’re gonna lose some friends, you’re gonna gain some friends. That’s gonna happen.” That’s definitely not to say you should just ditch your best friend since kindergarten because her boyfriend has a cheese mustache, but if this is a peripheral friend, maybe their sh*tty S.O. isn’t the hill to die on. Change can be difficult to face, but it’s okay to give way to the changing tides of interpersonal relationships.
To hear more from Jared and Jordana, listen to the U Up? episode below.
Images: Aranxa Esteve / Unsplash; Tenor (5)
