17 Incredibly Awkward Sexual Experiences

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Sex is a big deal, especially the first time. After episodes and seeming eons of longing and wanting, lusting and loving from afar, when a couple finally consummated, finally doing it is considered epic.

Except sometimes it isn't. The media has built up this idea that sex is earthshattering and awesome even the first time.

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In reality, sex can be awkward. It can be painful if you are a virgin. It can be strange if you are transitioning from a formerly platonic relationship. Or it can just be underwhelming.

Television doesn't always like to go there, but it is great when it does. A realistically awkward first time can bring a sense of reality to a show.

Of course, sometimes the reason for the awkwardness is exaggerated, cartoonish, comedic, or even catastrophic. Let's face it, even when TV tries to get real, it is still TV.




1. Chandler and Kathy -- Friends

Chandler and Kathy -- Friends
On Friends Season 4 Episode 11 Chandler admits that he is holding off having sex with his girlfriend because he knows her last boyfriend was Joey and based on what he heard through their shared wall, the sex was really great. He is disappointed when Kathy does not get as turned on during their sexcapades. Chandler never says the sex is bad for him, but Kathy not getting into it sort of ruins it for him. His female friends tell him it can take time for girls. Monica then teaches him about the supposed seven erogenous zones on a woman. After that, Chandler and Kathy give it another try and Kathy thanks Monica emphatically.

2. Noel and Felicity -- Felicity

Noel and Felicity -- Felicity
So, Noel and Felicity do not get to the sex part on Felicity Season 1 Episode 11, but it is still all kinds of awkward. Felicity and Noel make an "appointment" to have sex in his dorm. Noel prepares a romantic night, but Felicity comes at him, trying to take her research on the subject into account. She's aggressive, trying to "focus" and "get it over with." Some students walk in on them, and then everything catches on fire. Noel tries to keep things under control, still wanting to do it, but it doesn't work out. Eventually, Felicity realizes she isn't ready to lose her virginity.

3. Seth and Summer -- The O.C.

Seth and Summer -- The O.C.
After months of back and forth, Seth and Summer finally got together on The O.C. Season 1 Episode 19. Afterward, Seth tells Ryan how awkward it was, describing sounds and faces he made. "I sucked so bad. I was like a fish flopping around on dry land. Ryan, I was Nemo, and I just wanted to go home." When the couple tries again, Summer ends up limping, and Seth has some trouble seeing out of his eye. Seth assumes he is the problem due to Summer's reputation, but she later admits to him that she was also a virgin. This was one of the earlier instances of a show "going there" with an awkward first time. And one of the best!

4. Veronica and Duncan -- Veronica Mars

Veronica and Duncan -- Veronica Mars
On Veronica Mars Season 1 Episode 21, Veronica finally learns what happened to her on the night she can't remember. She was roofied and passed around to a lot of people. Her ex-boyfriend, who had also gotten roofied, found her passed out in a bed, and the two had sex. Considering they were both roofied, and Veronica couldn't even remember it the next morning, it can't have been the most enjoyable of first times. It doesn't help that Veronica woke up alone and under the impression that she had gotten raped. In fairness, she had been raped, just not by Duncan.

5. George and Meredith -- Grey's Anatomy

George and Meredith -- Grey's Anatomy
On Grey's Anatomy Season 2 Episode 18, George finally tells his long-time crush Meredith how he feels, and the two get together. However, on Grey's Anatomy Season 2 Episode 19, it is revealed that things went very bad between the two in the bedroom. Meredith was sad and drunk, and George was a sweet guy who cared about her so much, so she wanted it to work. However, she was in love with someone else and not really into George. She tries, but she burst into tears while George is on top of her. He storms out, hurt, angry, and humiliated.

6. Lane and Zack -- Gilmore Girls

Lane and Zack -- Gilmore Girls
On Gilmore Girls Season 7 Episode 2 Lane and Rory discuss the truth about sex. As Lane's highly anticipated losing of her virginity on her honeymoon was so miserable, she is convinced that sex is always bad for women and that the idea that it is healthy, wonderful, and sexy is a conspiracy by the media. Rory digs for details and learns that Lane and Zack attempted sex on the beach, which means dirty sand, cold nature, and shellfish crawling all over you. Lane is opting for a sexless marriage, but Rory advises her to try again indoors in a bed with a comforter.

7. Amy and Ricky -- The Secret Life of The American Teenager

Amy and Ricky -- The Secret Life of The American Teenager
On The Secret Life of The American Teenager Season 1 Episode 1, good girl Amy Juergens discovers she pregnant after losing her virginity over the summer at Band Camp. Amy tells her friends that it wasn't romantic or like the movies, and she wasn't even sure it was sex until she got a positive on a pregnancy test. Considering this was Amy's first time and she didn't know Ricky all that well, it is no real surprise that her their encounter wasn't earth-shattering. This series was known for commentating on sex and the American Teenager. The awkwardness of Amy's first time was one of its best moves.

8. Leonard and Penny -- The Big Bang Theory

Leonard and Penny -- The Big Bang Theory
Leonard wanted to have sex with Penny since the moment he met her. His dreams come true on The Big Bang Theory Season 3 Episode 1 when the two friends/neighbors finally decide to become a couple and end the episode in bed. On The Big Bang Theory Season 3 Episode 2, they both express that while the encounter was "fine" or "okay," it wasn't exactly great. Going from friends to more than was weird for both of them. They talk about going back to being friends, but end up in bed together again and realize that sometimes you need to get over the hump.

9. Kemal and Lady Mary -- Downton Abbey

Kemal and Lady Mary -- Downton Abbey
On Downton Abbey Season 1 Episode 3, Lady Mary Crawley meets Kemal Pamuk, and sparks fly. He comes to her bedchamber and seduces her, promising that nobody needs to know and she can tell whomever she marries that she is a virgin. However, while they are in the middle of the act, Kemal has a heart attack and promptly dies. This is possibly the most awkward on this list, because, well, death. Lady Mary must then move the body with the aid of her maid and her mother. Explaining why he is in her bed to her mother is awkward, but at least nobody else knows. Well, except Daisy.

10. Matty and Jenna -- Awkward

Matty and Jenna -- Awkward
On Awkward Season 1 Episode 1 invisible girl Jenna Hamilton loses her virginity at summer camp to popular guy Matty McKibben. They do it in a utility closet. She tears up because it hurts, but she doesn't want him to know she's a virgin, so she tells him its allergies and to keep going. It was good enough for her still be totally into Matty, but when she tries to ask him out afterward, he tells her that nobody can know he likes her. Jenna puts her blog-staus up as "Rubbed Raw and Reeling" Rubbed Raw? It doesn't sound like the most comfortable of first times.

11. Ted and The Slutty Pumpkin (Naomi) -- How I Met Your Mother

Ted and The Slutty Pumpkin (Naomi) -- How I Met Your Mother
On How I Met Your Mother Season 7 Episode 8, Ted finally tracks down the girl in the Slutty Pumpkin costume that he met at a Halloween party ten years prior. Both he and Naomi have been searching and waiting for each other for so long, neither wants to admit that things don't work between them. They are incompatible in all ways but especially physically. Ted tries to dump her but gets caught up in nostalgia, and they end up in bed together. "No part of it felt right," Ted told Robin and Barney, "at first there was too much eye contact, then not enough, where do you look during sex?" Finally, thankfully, the two admit their incompatibility and go their separate ways.

12. Dan and Blair -- Gossip Girl

Dan and Blair -- Gossip Girl
On Gossip Girl Season 5 Episode 18, After being walked in on, or the awkwardness of Dan's Cabbage Patch Kid starring at her, Dan and Blair get a hotel room and get down to business. They both tell each other it was "wow," but later admit that it was terrible, mind-numbingly dull, and incredibly unsexy. Both fear that their connection is purely intellectual, but after a lot of alcohol, the two give it another go in an elevator and find that they are sexually compatible after all. As Dan said, sometimes you just have to throw out the first pancake.

13. Schmidt and Elizabeth -- New Girl

Schmidt and Elizabeth -- New Girl
On New Girl Season 2 Episode 23, the gang all tell each other how they lost their virginity. Frankly, most of the stories are not so great (Except CeCe's because she lost it to Mick Jagger). However, the most awkward was Schmidt and his college girlfriend, Elizabeth. Schmidt applied too much lubricant everywhere. Elizabeth couldn't see through the lube, and Schmidt couldn't get a proper hold on her. He literally slid off the top bunk onto the floor. He crashed into Nick, who was supposed to make himself scarce but had gotten high and was now an unwelcome third-wheel.

14. June and Mark -- Don't Trust the B---- in Apartment 23

June and Mark -- Don't Trust the B---- in Apartment 23
On Don't Trust the B---- in Apartment 23 Season 2 Episode 17, June finally talks to Mark about his feelings for her and realizes she might have feelings for him too. When she talks to him about it, they end up in bed together for what is awful sex. They keep doing it, trying to get it right, incorporating public places and wigs, until Chloe forces them two admit that they don't work sexually. Not everybody is compatible that way, and that is okay. Sometimes what makes sense on paper doesn't in the bedroom. At least, that's what the sitcoms teach us, so it must be true.

15. Roberta and King Richard -- Galavant

Roberta and King Richard -- Galavant
On Galavant Season 2 Episode 8 King Richard, who has gray hair and was previously married, finally loses his virginity. His virgin status, given his age, had been a running joke on the show for a while now. Even after Roberta got introduced as a love interest for Richard, it took him a while to realize she was into him and do something about it. While what they have seems real, Galavant is all about music and humor. The two lovebirds sing about hooking up in "Finally" a song that is a tribute to "Summer Nights" from "Grease." The lyrics state that Richard got weepy and dropped Roberta at least once.

16. Joe and Beck -- You

Joe and Beck -- You
Everything about Joe and Beck is awkward because Joe is a creepy stalker; the couple's first time together is no exception. On You Season 1 Episode 3, Joe goes over to Beck's house to show her that he is the guy for her. It starts kind of sexy, but then Joe prematurely ejaculates, effectively wrecking the mood. It is surprising this reason isn't on this list more, as PE is pretty common, and guys tend to take it pretty hard. In this case, well, we would feel bad for the guy if he weren't a creepy stalker.

17. Jonah and Amy -- Superstore

Jonah and Amy -- Superstore
So, Jonah and Amy's first time wasn't awkward in and of itself. On Superstore Season 3 Episode 22 their office romance finally heats up in the photo lab aka "the bang room." It could have been awkward because it was a first time, or because Amy was pregnant, but that wasn't it. It was pleasurable for Amy, and Jonah had an orgasm. The awkward came when they discovered that their encounter was being live-streamed to every Cloud-9 internationally. You'd think someone from their store would have gone to the photo-lab and told them they were on camera, but nope.

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YOU Season 1 Episode 3 Quotes

How exactly does one get rid of a body? I can't just Google this kind of thing without leaving a pretty damning evidence trail.

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Joe Voiceover