Sex on television can be fairly unrealistic. For instance, it’s not possible for someone as cute as Zooey Deschanel to bomb with someone as equally cute as Justin Long (see New Girl episode #8). That said, the bottom line rings true: sex isn’t always pretty. Time and time again we learn that scented candles and starfish lingerie straps prove useless in diffusing the awkwardness of human intimacy. Which is why this Valentine’s Day we’re cutting through the hoopla and spotlighting some of the biggest romantic misfires in television history (no pun intended). And since we’re not total curmudgeons, we’d like to point out that, sometimes, bad sex is beautiful. It can blossom into true love, bring a couple closer together, or even save a friendship. Just click through and see for yourself. And be sure to add your own favorite awkward couplings in the comments!

Seth gets foreplay advice from his dad, The O.C.

The Valentine’s Day Singles’ Gala has arrived and the O.C. is rife with sexual tension. Marissa is throwing herself at Ryan. Luke is throwing himself at Marissa’s mom. And Seth and Summer have sex for the first time. It is not good, which means only one thing: father-son sex talk! Sandy pontificates on the importance of foreplay, which causes Seth to nearly vomit in his mouth. Nonetheless, he takes his dad’s advice and even worse, injury-inducing sex ensues. After the gala Seth and Summer have a heart-to-heart and slow dance to “Wonderwall” (on vinyl) instead of doing the dirty. Wise move. (On a side note, Luke’s “You have always been the coolest mom” line totally worked!)

On his first time: “I did make some faces in the middle that I wish that I could take back, but I can’t. And there’s also sort of a whiney noise that came out towards the end — that probably wasn’t my finest hour. 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.” – Seth Cohen

Jonathan tries polyamory, Bored to Death

Unsatisfied with monogamy, Stella convinces Jonathan to try an open relationship with her ex -boyfriend Warren, a struggling comedian. What starts as an overnight group cuddle evolves into more and Jonathan becomes self-conscious about his size. In a fit of “menticide” he makes Ray check him out in a public restroom (just like Hemingway did for Fitzgerald). Ray confirms that Jonathan is in fact an adult male, but by next episode Jonathan gets cut out of the polyamorous experiment all together when Stella announces she wants to be exclusive with Warren. Poor Jonathan. He really tried on this one.

On the other guy: “It was frightening! It was like an elephant tusk!…I think I may have the smallest penis in the world.” – Jonathan Ames

Felicity and Noel try to have dorm sex, Felicity

Never have two people in the history of television talked about having sex so much in one episode without actually having sex. It starts when Felicity returns from winter break and informs Noel they are going to do the deed. He promptly drops his new iMac, an omen of bad things to come. By the time their scheduled sex date arrives (Wednesday, 8pm) everyone including the mailroom guy knows their plan. Well, everyone except for the computer guy, who barges in Noel’s room with the repaired iMac and two friends in tow. At the sight of two sort-of naked people, computer guy drops the iMac (bad omen, again) and his friend knocks over a candle, setting Noel’s Christmas tree on fire. The entire floor evacuates and the two reschedule, but Felicity ends up losing her virginity to a hot art student a few episodes later.

On propositioning your RA: “I’ve decided… that you and I should have sex.” – Felicity Porter

Louie gets bum-rushed and sleeps with a school mom, Louie

As a whole, this episode serves as a cautionary tale on the perils of dating. First Louie is nearly run down by a homeless man who gets decapitated by a garbage truck. This all takes place on his way to meet Janice, a woman he hopes to sleep with but doesn’t. Then he arranges no-strings sex with a school mom, who ends up having masochistic daddy issues in the bedroom. We should mention that Louie learns this only after he has returned from the grocery store with her Vagiteen (a fictional panacea for irritated female parts) and blueberries (no apparent relation to the Vagiteen). In conclusion, the title of this episode, “Bummer/Blueberries” should become a euphemism for any depressing dating experience.

On romantic boundaries: “Um, no, you are not buying my Vagiteen. I’m not going down that road, I told you. I just need you to pick it up.” – Dolores

Sloan discovers something in Eric’s search history, Entourage

After Sloan stumbles upon “anal sex” in Eric’s search history, they decide to try it for the second time in their relationship — this time under the guidance of Google. Mid-penetration their frustrations escalate into a fight, but Sloan and E quickly realize that now is not the time to turn on one another, figuratively speaking that is. Anger fizzles into laughter and they realize there’s nothing wrong with the old-fashioned way. Aww.

On anal sex: “I like your vagina, is that so wrong?” – Eric “E” Murphy

The gang gets a hang-up, How I Met Your Mother

Leave it to How I Met Your Mother to make the absolute worse thing you can visualize during sex, kind of sweet. It all starts when Kevin tells the gang it’s normal to end up with someone like your parents. Soon Lily and Marshall realize they have married their dads, making for some real awkward foreplay and dirty talk. Unable to seal the deal, we wonder: will Marshall and Lily be able to have sex again? Meanwhile, Barney is finally about to sleep with his girlfriend Nora when he realizes she is just like his mother. A cutaway leads us to think they suffered the same fate as Lily and Marshall, but later, in classic Barney form, he tells the gang he simply “turned it around.” And then adds he would be lucky to end up with someone just a tiny bit like his mom. This touches Lily and Marshall (the second part) and they promptly leave to have sex.

On parental fantasies: “Hey, you know what? I’m a real lucky guy. Cuz I married my dad.” – Marshall Eriksen

Elaine and Jerry have sex to save the friendship, Seinfeld

After Jerry learns Elaine faked it with him, he begs for another shot. She turns him down, causing Jerry to fixate even more on her “sexual perjury.” Jerry becomes so angry with Elaine that she finally agrees to have sex with him. They try again to no avail, and the aftermath is abysmal: Jerry in bed whimpering and Elaine on her side, flipping through a magazine. Jerry begins to blame George, who has been obsessing over his own sexual performance all episode long. But then Elaine asks for some mango and Jerry remembers its stimulating power. Friendship saved! Watch the scene here.

On orgasms with Jerry: “Fake, fake, fake, fake.” – Elaine Benes

The jackrabbit, Sex and the City

We learned a lot about “sexpectations” from Sex and the City — mainly that they result in disappointment. Take the night Carrie convinces herself to have a fling with Howie Halberstein, Harry’s best man. “After all,” she muses, “how bad could he be?” Very bad, it turns out. The next day Carrie arrives to Charlotte’s wedding with a “sex sprain” from an evening of jackrabbit sex and is forced to tell Howie she doesn’t want to see him again. Ego bruised, Howie gives a very pointed wedding toast (or “roast” as Stanford calls it) in which he ends up accusing Carrie of using him for sex. Ouch (on many levels).

On love: “It’s tough out there. People don’t care like they used to. People leave you hanging. People are a bitch… So here’s to love. And love means, never, ever, having to say, you used me for SEX! Mazel tov!”– Howie Halberstein

Leonard tries to cyber, The Big Bang Theory

In an effort to sustain their long-distance relationship, Leonard and Priya decide to have cybersex. Leonard begins with some terrible dirty talk (“You’re a naughty girl. And, and, uh, I, I want to punish you with my love?”), but things pick up when Priya takes control of the situation. Unfortunately Leonard’s screen freezes just as she is about to remove her shirt. The next time they Skype, Leonard leads with some dirty talk he (clearly) scripted himself, but is cut short when he learns Priya’s parents are in her room. Man, you’d think the virtual sex thing would really be a physicist’s bailiwick. Watch the clip here.

On cyber courtesy: “Please let me know when you and your girlfriend are done hogging the bandwidth for your self-abuse. I’m trying to stream a movie on Netflix in here.” – Sheldon Cooper

Eric “surprises” Donna, That ’70s Show

Inspired by an adult film, Eric tries something new with Donna in bed. We aren’t explicitly told what this thing is (you’ll find a heated discussion thread on the topic here), but we know it’s enough to send Donna running for the hills. She then tells Jackie, who is equally disgusted. Later Eric confesses he only wanted to do something special for their 100th time. Donna is touched, but demands that he inform her the next time he makes plans.

On introducing new moves: “Do me a favor. Next time you’re going to do something weird, give me a little more warning. So I can brace myself. Or tell you to back the hell off… Because no matter how much I love you, that was unpleasant.” – Donna Pinciotti