Over the course of its nine seasons, Seinfeld covered all areas of the minutiae of daily life. As a sitcom that explored the irritating side of taking part in a civilized society, dating formed the basis of a lot of the show’s funniest episodes. Being single and dabbling in the dating pool can be frustrating, difficult, and bring up insecurities – especially if you’re as neurotic and misanthropic as Jerry, Elaine, George (especially George), and Kramer.
Some of Seinfeld’s most relatable storylines revolved around the doomed romantic exploits of its characters. So, here are Seinfeld’s 10 Best Episodes About Dating, Ranked.
The Stand-In (season 5, episode 16)
At the beginning of “The Stand-In,” George is ready to break up with his girlfriend Daphne because they have absolutely nothing to talk about and he’s bored in the relationship. However, when his friend Al Netche tells Daphne that George is a bad seed and he’ll end up hurting her, George becomes determined to prove him wrong.
Despite the fact that boredom has turned into active dislike, George sticks with Daphne. He even tells Jerry that he’ll go as far as marrying her if he has to. And because we know what George is like, it’s easy to picture him actually doing that. In the end, she breaks up with him.
The Cartoon (season 9, episode 13)
George suffers from a Freudian meltdown in the season 9 episode “The Cartoon,” as he realizes his new girlfriend, Janet, looks exactly like Jerry. He tries to justify his relationship with Janet to himself by trying to find things they have in common that aren’t physical. However, he’s horrified when Janet remembers that when George first approached her, he commented on her looks.
At the end of the episode, she gets gum in her hair and has to cut around it to get it out. With her new hairstyle, she’s a dead ringer for Jerry, and George just can’t look past it anymore.
The Switch (season 6, episode 11)
After meeting his humorless girlfriend’s roommate who laughs a lot more at his jokes in season 6’s “The Switch,” Jerry finds himself in a pretty awkward predicament: he wants to swap his girlfriend for her roommate. At first, George tells him that this can’t be done. But after a long night with lots of coffee, they come up with a plan: suggest a threesome.
Much to Jerry’s surprise, the gambit works a little too well and both women are into it. George is ecstatic at the outcome, saying, “This is like discovering plutonium by accident!” but Jerry decides he can’t go through with it because he’s “not an orgy guy.”
The Engagement (season 7, episode 1)
“The Engagement” kicked off season 7’s story arc (George’s engagement to Susan) with Jerry and George making a pact – although Jerry later denies that it was a pact (“You stuck your hand out…so I shook it”) – to finally move on with their lives and get married. George goes straight to Susan’s apartment to propose and immediately has second thoughts about it.
Meanwhile, Jerry is put off by the idea of marriage altogether by a hilarious monologue delivered by Kramer (“You have to ask permission to use the bathroom – is it all right if I use the bathroom now!?”). George’s instant cold feet are sadly relatable.
The Big Salad (season 6, episode 2)
In “The Big Salad,” Jerry dates a woman who, he finds out, used to date his mortal enemy, Newman. And as baffled as he is that they once dated, he’s even more baffled that she didn’t break up with Newman; Newman broke up with her! In the end, he can’t wrap his head around it and she cuts ties with him.
Meanwhile, George shoots himself in the foot when his girlfriend takes credit for buying Elaine a salad that he actually paid for. He corrects the error and it ends up getting back to his girlfriend, who sees him as too petty to date. But to be fair, it was a big salad.
The Pie (season 5, episode 15)
Sometimes, little things can ruin a relationship. If you’re just getting to know each other and you’re not totally clicking yet, it’s easy to latch onto one small thing that invades your conception of that person.
In season 5’s “The Pie,” Jerry offers his new girlfriend, Audrey, a piece of his apple pie in Monk’s Café, insisting that it’s the best apple pie in the city. Without saying a word, simply by shaking her head until he stops offering, she refuses to take a bite of the pie. Jerry just can’t let it go, and it leads to the end of the relationship.
The Boyfriend (season 3, episodes 17/18)
In the two-parter “The Boyfriend,” Jerry becomes friends with baseball player Keith Hernandez. Although it’s a platonic friendship between two straight guys, there are romantic overtones. Jerry waits impatiently for Keith to call, worrying that he never will, and then isn’t sure about shaking his hand at the end of their first “date.”
When Keith starts dating Elaine, Jerry becomes jealous. At first, he’s jealous of Keith for dating his ex-girlfriend, but as the episode progresses, he becomes jealous of Elaine for dating a ballplayer. He keeps flip-flopping until a confused Elaine says, “Before, you were jealous of me. Now, you’re jealous of him?” Pricelessly, Jerry replies, “Ah, I’m jealous of everybody!”
The Lip Reader (season 5, episode 6)
In season 5’s “The Lip Reader,” George is dating a woman named Gwen. When she inevitably breaks up with him, she says, “It’s not you, it’s me.” And George, in one of his most iconic moments, says, “You’re giving me the ‘It’s not you, it’s me’ routine? I invented ‘It’s not you, it’s me!’ Nobody tells me it’s them, not me! If it’s anybody, it’s me.”
Meanwhile, Jerry has started dating a deaf lineswoman (played by guest star Marlee Matlin), who can read lips. George concocts a scheme to bring her to a party to read Gwen’s lips and find out why she broke up with him.
The Face Painter (season 6, episode 23)
While David Puddy is painting his face to attend a hockey game and Jerry holds off on thanking a friend of his for giving him the tickets, George dates a woman that he thinks he’s in love with. He’s so confident that he feels ready to say, “I love you,” for the first time in his life. (Well, he said it once to a dog, but this is the first time he’s saying it to a human). It’s always tough to tell someone you love them – as Jerry says, it leaves “a pretty big matzo ball hanging out there.”
After he musters up the courage to confess his love, she tells him, “I’m hungry. Let’s get something to eat.” He later finds out she has bad hearing in one ear, so he tries again, speaking into her other ear, and it turns out she heard him the first time after all.
The Fix-Up (season 3, episode 16)
When George complains about his lack of success in the dating world to Jerry, and Elaine’s friend Cynthia tells her that she just wants a guy who’s desperate enough to adore her, the two decide to set them up on a date. They’re both initially apprehensive but agree to a phone call. George is thrilled after the call, but his confidence is shot when Elaine tells him that Cynthia didn’t even mention the quality of the conversation: “All right, I’ll go on the date, but that’s that.”
Jerry and Elaine convince him to go into the date with an open mind. They end up sleeping together and after George uses a defective condom that Kramer gave him, they face a pregnancy scare. They almost hit it off, but George’s eating habits put her off.
