Regrets. We all have them, and unfortunately no one is immune. Not even celebrities (which should make us feel at least a bit better). Anyway, we are going to recount some regrets of the rich and famous right here for you. These are the 15 Biggest Sexual Regret Stories from Celebrities. And if you ever thought that your first time was awkward or that you really messed things up in bed, then you have got to read these stories! They are pure embarrassment gold.
For instance, we have not one but two Jonas brothers on our list. We won’t reveal anything right here, but let’s just say that you should make sure to pre-select any music you want to play during sex. We also have musical icons such as Britney Spears, Cher, and Kanye West. We know what you’re thinking: Kanye West actually regrets something? You’ll just have to see what we mean. There are also stories from Simon Cowell, Ansel Elgort, Armie Hammer, and more! Read on and don’t weep, because everyone goes through some embarrassing moments. Even under the sheets.
It is always nice to get a dose of reality from the rich and the famous. They may look high and mighty and as if they have everything together, but they too have their stumbles and falls. And if they are Shia LaBeouf, they have huge splats! We hope that you enjoy our list and infuse some humor and lightheartedness into your day. Just remember to learn from these celeb snafus.
15. Simon Cowell
We will start off our list with a wacky sexual regret that makes us scratch our heads. Apparently a couple offered Simon Cowell 100,000 quid to watch and critique their sexual activities in the bedroom. He turned them down, only to say afterwards that he wishes he hadn’t. Um, what? Okay, we understand that it was for a lot of money, but Simon Cowell is already really rich, is he really going to notice the extra 100,000? Not to mention that he kind of built his reputation on being a really mean and scowling judge, is that really the guy you want judging you in the bedroom? Call us crazy, but the thought of him sitting there in a black t-shirt just grosses us out.
14. Britney Spears
For all the amazing things that Britney Spears has accomplished, there is no doubting that she has had her fair share of troubles. Yet she still earns the love of her fans, perhaps more now than ever, thanks to her comeback. Anyway, back in the day, Brit married this dude named Kevin Federline. Maybe you remember him? So, she and K-Fed ended up making Britney and Kevin: Chaotic, a weird sex tape celebrity fiasco that was a complete flop. Not to mention awkward. And slightly disturbing. We totally feel you, Britney. All is forgiven because everyone makes mistakes, but how do you not regret something like that? The important thing is that she has since moved on and is now living the good life with her fantastic sons.
13. Kanye West
Kanye West just seems like the kind of guy who would not really have any regrets. We aren’t even sure if the dude has a conscience. But anyway, he did reveal that he regrets not showing off Kim Kardashian’s nude figure in more of his music videos. Well now, does that even count as a legit regret? Whatever. It’s not like Kanye is going to come out and say how he used to suck in bed. Kanye shouldn’t be too worried if he is concerned though, because even without putting her in the videos, everyone knows what Kim looks like naked. After all, her butt broke the Internet. People also know that she is the lovely wife of Kanye. So we aren’t quite sure what the rapper is whining about, but are we ever?
Cher is a senior citizen by now (69!), so we guess that she can air out all of her dirty laundry. Perhaps one of the more shocking things that she revealed about her sexual past was that she actually regrets not staying in an affair longer with Marlon Brando. We must say, this may be the first time we have heard someone not regret getting into an affair. Oh, Cher. The diva also said that she regrets turning down romantic advances from Elvis Presley. The King himself! Of course we can understand that regret! Good thing Cher believes in love after love.
11. Armie Hammer
Armand Douglas Hammer’s biggest sexual regret is downright frightening! He was getting it on with a former girlfriend when she reportedly pulled out a knife on him! She wanted to stab him! During sexual intercourse. What the what?! According to Armie, she noticed that he didn’t have any real scars on his body, so she wanted to give him a good one. In fact, he said that the girl pulled out a butcher knife. How the heck does one sneak a butcher knife into bed? Obviously, he never saw that girl again. And hopefully he called the police on that whacko!
10. Kris Jenner
Of course you can’t have celebrity sexual regrets without mentioning the Kardashian-Jenner clan! This one involves Kris Jenner, who back in the day was flying on an airline with Bruce (Caitlyn) Jenner. The couple ended up going into the bathroom and totally getting it on. They had sex and came out of the loo and figured that no one was any the wiser for it. But, upon leaving the aircraft once they landed, a flight attendant got on the intercom and publicly congratulated Kris and her partner for joining the “Mile High Club.” Doh! If this isn’t a life lesson, we don’t know what is!
9. Jenny Molen and Jason Biggs
This starry couple has a funny yet so wrong sexual regret. So, it was Jason’s birthday and Jenny decided to surprise him by hiring a female stripper to give Jason a show. Well, we don’t know where Jenny got the contact info for this stripper, because the girl was no good. Jenny actually ended up watching the whole fiasco unfold while laughing hysterically. Jason was just kind of like “um…okay,” creating what was apparently just an awkward attempt at some birthday fun. Nice try, Jenny, but we hope that there was a back-up gift or something. Come to think of it, is a hired stripper ever successful?
8. Nick Jonas
Nick Jonas, the youngest, curly-haired cutie of the Jonas Brothers trio! He always had such a cutie-pie look to him. He may now be older and more mature, but he still has that adorable baby face. Now he just has a gorgeous masculine body to boot! Sounds like a win-win! Anyway, his first sexual experience was not a win-win. He lost his virginity in a depressing and awkward way. He was trying to set the mood, so he put his iPod music on. Trouble is, it was on shuffle and it started playing a depressing emo song. Though if he’s like some guys and their first time, perhaps they only had to listen to the song for 15-20 seconds! When asked if he’s ever had sex to his own music though, he openly denied it saying it would be too weird.
7. Jennifer Lawrence
Oh, J-Law. We will never stop loving you! Even when you reveal your sexual regrets. That is just what makes you the down-to-earth celebrity that you are. Anyway, in a not-so-surprising revelation, Jennifer said that for her very first sex scene, she was nervous, so she turned to alcohol. She proceeded to get drunk and then had to do her very first onscreen sexual shot with none other than Chris Pratt. If you ask us, we would want to be totally sober for such an experience; no way we want the details to be fuzzy! If only we all could have such an opportunity…
6. Vicky Pattison
Vicky Pattison starred on a reality TV show, so it really shouldn’t surprise us that the English starlet had a sexual regret or two that is related to her job. After starring on the TV series Geordie Shore, Vicky spoke out and said that she actually regretted having sexual intercourse on television. Oh, really? You don’t say! No offense, but we kind of think it is because of actions like having sex on reality TV that has caused such a nonchalance related to intimacy; instead of it being the relationship building or seen for it’s complete value.
5. Michelle Keegan
English actress Michelle Keegan is usually true to her British charm and tends to keep a fairly low profile. As a result, it was actually really out of character for her to say what she did; but when speaking to some reporters she was not afraid to let them know just how horny she was feeling lately! A bit of backstory: her husband had been away from home for 2 weeks. So we can definitely understand. She was sexually frustrated, that’s all! Even so, it is a bit embarrassing to let the whole world in on that dirty little secret. No word on how her hubby received that news!
4. Ben McKenzie
This is actually a pretty funny one. Ben McKenzie can definitely relate to the awkward early-20s feeling of bringing girls home. When he was 22 years old, he was seriously embarrassed over the fact that he was still sleeping in a bunk bed. Pretty hard to get some action with a bunk bed, right? Ben was actually totally transparent about it and he warned his girlfriends beforehand, so at least he had that going for him? While he said that he did have a hookup or two in that bunk bed, there was no way that a girl was going to let him bang her in that. Oh well! Looks like he had to graduate to a big boy bed.
3. Ansel Elgort
Celebrities are just like us, sometimes. As for Ansel Elgort, he can totally relate to losing his virginity at a young age. The poor guy was just 14 years old the very first time he got in the sack with a girl. And it wasn’t fun at all. He said that neither he nor the girl knew what they were supposed to be doing. On top of that (no pun intended) Ansel did a really poor job of setting the mood (so probably no candles and fancy dinner). So there was really nothing romantic or intimate about it, but really, how much can you expect from a 14 year old boy? We wonder how things have improved for him since then!
2. Kevin Jonas
The Jonas brothers were like the modern-day Hanson brothers. They just seemed so pristine and polished, prim and proper. And for a while there, they were! As for Kevin, he stayed away from sexual intercourse until he got married. So the first time he had sex was with his wife and he was kind of let down, in all honesty. It wasn’t necessarily his wife or her performance, he was just kind of expecting sex to be super amazing and the time of his life. So when it didn’t live up to all the hype, he was kind of just like…”that’s it?”
1. Shia LaBeouf
Shia LaBeouf has done plenty of embarrassing and regrettable things during his lifetime, so are you surprised he tops out the list? And he’s still young, so he has so much potential for future headlines. As far as sexual regrets are concerned, he has a pretty interesting one. He tried to look all experienced and macho during his first sexual encounter with a girl, but it was a total flop. He just sort of based things off of what he had seen in porn films. That means trying to look big and mighty, as well as working on some sex moves that he wasn’t even sure how to maneuver. Shia also admitted himself he wasn’t well-equipped; so let’s just hope the girl is as good an actor as him!
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