With one of the most groundbreaking sitcoms from the 80s following a bunch of New York socialites, it’s no secret that they’ve been on more than a few dates. As the group is always seeking companionship, their selfishness always gets in the way, leading to some hilarious break-ups.
Over the course of Seinfeld’s nine seasons, Jerry was involved in over 40 relationships, and Elaine was in 29 relationships too. The group of serial daters did have some serious relationships, however, but they all had very varying degrees of success.
Elaine And Dick
In one of the worst downward spirals of any character in the show, Dick suffers a relapse into alcoholism inadvertently caused by none other than Jerry. Because of this, Dick lives up to his name by heckling Jerry at his stand up shows and being a terrible boyfriend to Elaine, leading to being broken up with and losing his job in the process.
To think, if Jerry hadn’t had accidentally given him vodka and cranberry juice, Elaine and Dick could have had a lasting relationship.
George/Jerry And Marlene
George was not the only person to date Marlene, a woman he found incredibly annoying, as Jerry started dating her not long after, which is one of the reasons why Jerry is a bad friend.
However, just like George did, Jerry starts to find Marlene annoying as well, but it wasn’t Jerry who broke up with her. Marlene hilariously breaks up with Jerry after his stand up routine because she didn’t find him funny.
Elaine And Owen
Owen first appears in the episode “The Alternate Side,” which is most famous for Kramer practicing the line “these pretzels are making me thirsty” for a Woody Allen movie. But Elaine’s weird relationship with the 66-year-old is still the strangest thing about it.
Elaine desperately wants to break up with Owen, as she’s constantly acting like more of a carer than a girlfriend, but he has a stroke before she’s able to rip the band-aid off, leaving her stuck with him for much longer than she wants.
Jerry And Meryl
When it comes to Friends and Seinfeld, the debate over which show is better will rage on for decades, but Courtney Cox’s feature as Meryl is one of the most hilarious of Jerry’s girlfriends.
When Jerry pretends that Meryl is his wife just so they can get a discount at a dry cleaner, they start acting like a married couple in their personal lives, which turns their relationship into quite a grind as they become a cliched unhappy married couple.
Elaine And Dr. Reston
Though it surely breaks some kind of doctor’s code, as they can’t possibly be allowed to date their patients, Elaine sparks up a relationship with her psychiatrist, Dr. Reston.
The two seem to be in love, as they even go on a trip to Europe together and make out on balconies in front of some beautiful vistas, but it isn’t enough for Elaine, as she breaks up with the doctor when they land back in New York.
Jerry And Rachel
Rachel had a good run with Jerry, as she was Jerry’s second most dated girlfriend after Elaine. The character featured in several episodes throughout season five, most hilariously in “The Raincoats,” as she and Jerry made out over the entire duration of a Schindler’s List screening.
Jerry’s relationship with Rachel could have lasted even longer, as it was actually her who broke up with him.
Kramer And Marion
If there’s one thing Kramer is it’s passionate, and that’s no different when he strikes up a relationship with a woman, and his bond with Marion was like two kids in love.
However, strangely enough, this relationship between two consenting adults seemed like a forbidden love destined to fail, as the library cop prohibited their relationship in the library, which was the only place they spent time together.
Jerry And Elaine
Jerry and Elaine have been on-again, off-again possibly even more than Ross and Rachel, and it’s possible that they were destined to be together. But given the on-set rule of Seinfeld, which is “no lessons, no hugs,” it was unlikely that they were ever going to end up together.
Besides that, they’ve done some awful things to each other, and taking back his proposal to Elaine was one of the worst things Jerry ever did to her.
Elaine And Puddy
Though her on-again, off-again relationship with Puddy was one of the most annoying things Elaine ever did, Puddy was one of the most lovable characters in the show, which had so few characters audiences could genuinely get behind.
It was his every-man likeability – loving sports, being a mechanic, always high-fiving – that made him one of the viewers’ favorite boyfriends of Elaine. He was Elaine’s most successful companion, as he was always seemingly back in the picture.
George And Susan
Being the longest-running relationship of the whole series, George and Susan rarely ever saw eye to eye and was more of a toxic relationship than anything.
After meeting each other during George and Jerry’s TV show pitch to NBC, a story arc that is arguably overrated, the couple stayed together for a surprising amount of time. And it’s the most successful relationship of Seinfeld chalked down to the fact that they never broke up, even if George was over the moon when she died.