The serial dater, Jerry, dated 66 different women over the course of Seinfeld's nine seasons. Generally, he'd love the initial thrill of getting to know someone, but back out before anything serious could develop.
But as much as anyone around him, Jerry craved love and affection. There are times he earnestly wanted to commit to another person, but something just stood in the way. Jerry made decisions that impacted his relationships, for good or ill. Sometimes, he ended up with happy outcomes, and other times, quite the opposite happened.
Best Decisions
When He Broke Off Engagement With Jeannie
Jeannie Steinman is the woman who saves Jerry from nearly being hit by a car in "The Invitations." The man is impressed that they have the same initials and order the same food at Monk's Cafe, and he thinks he's in love.
Jerry sees himself in Jeannie and decides to propose without adequate thought. But thankfully, they decide to end it in the following episode. Jerry says his breakup was the first truly mutual one in relationship history, without any feelings of guilt or remorse, and fans couldn't agree more. Calling off the engagement was a wise decision and one that they made in the nick of time. Jeannie and Jerry couldn't stand each other and there's no way they could have stayed married for long.
When He Confronted Nina About Her Plagiarized Love Letter
Jerry dated an artist named Nina in "The Letter" who displayed unhealthy relationship behavior. The couple faced minor bumps every now and again, and Nina expected Jerry to take sides between her and his friends.
The breakup was finally caused by Nina sending Jerry a plagiarized letter from the Neil Simon film, Chapter Two. She could have authentically articulated her thoughts, but to pass off someone else's words as her own was deeply problematic. The incident is also one of the times Seinfeld tackled deep issues, and yet, stayed true to its comical tone.
When He Agreed To Race Duncan For Lois
Jerry, the ardent Superman fan is excited to be dating a woman named Lois in "The Race". Things are going well until it's revealed that Lois' boss, Duncan Meyer, is Jerry's adversary from school. No one besides George knows that in the ninth grade, Jerry had got a headstart in the footrace and won.
Duncan challenges Jerry to a rematch, which the latter reluctantly accepts for Lois' sake because her job is in danger. "The Race" is also one of the Seinfeld episodes that ends perfectly. Jerry wins again, due to a headstart, and Lois gets to keep her job.
When He Questioned Gennice's Lack Of Empathy
In season 6's finale, Jerry dated Bette Midler's understudy, Gennice Graham, who exhibits all the warning signs of a bad girlfriend. She's inconsolable when she drops a hot dog on the floor or while watching Beaches. Jerry thinks Gennice is overacting during both of these times and doesn't feel the need to comfort her.
Strangely, Gennice exhibits no emotion when she learns about her dead grandmother. Her reaction prompts Jerry to ask, "So you don't care when your grandmother dies, but a hot dog makes you lose control?" Jerry listens to his instincts and goes home alone at the end of the episode.
When He Chose To Stay Friends With Elaine
Jerry consciously decided to stay friends with Elaine after their breakup because she meant a great deal to him. At the beginning of Seinfeld, the two were clearly over, and it was revealed that Jerry had blocked out the entire time they were a couple. Nonetheless, both of them wanted to remain close friends and succeeded at it.
While Jerry and Elaine didn't work out as a couple, they worked towards their friendship. He promised her honesty and straightforwardness every step of the way. Elaine enriched Jerry's life, and fans think being friends with her was the greatest decision he ever made in Seinfeld.
Worst Decisions
When he Ended Things With Margaret Because She Used To Date Newman
Undoubtedly, one of the worst relationships decisions Jerry ever made was to end things with Margaret because she used to go out with Newman. He thought she was way too good to be going out with someone like him.
What Jerry failed to understand was that perhaps she actually liked him and it was nothing to be fussed about. He couldn't even bring himself to kiss Margaret and let her slip away.
When He Showed Up Unannounced At Tia's Workplace
Jerry used to date a model named Tia Van Camp, who dumped him for picking his nose while stopped at the traffic light (even though he wasn't). Jerry maintained it was only a scratch, but Tia's viewing angle suggested otherwise.
"The Pick" stands out for being one of those rare moments in the show when fans witness Jerry getting a taste of his own medicine. Dumped for false pickings, being the professional that Jerry is, he decides to crash Tia's workplace. He makes a ridiculous speech in defense of nose pickers who've been caught. Tia gets in the elevator as quickly as possible and leaves Jerry standing in the hallway. It's such an unprofessional move on Jerry's part and it tosses their relationship into the bin.
When He Didn't Stand Up For Sheila
In "The Soup Nazi," Jerry's girlfriend, Sheila, and the irascible soup chef, Yev Kassem, argue back and forth about his shop etiquette. Kassem doesn't like it when people kiss in his waiting line, and Sheila makes a case for her free will. So what does her boyfriend, Jerry, do? He chooses soup over Sheila and sides with the irate chef in the fight.
Later, when a puzzled Elaine questions Jerry about choosing soup over a woman, he meekly replies, "It was a bisque." His relationship is in grave danger (as it should be) because his top priority was soup. It's an unbelievably awful decision on Jerry's part, and it even surpasses George Costanza's lamest acts in every way possible.
When He Took Vanessa To Vermont Early On In Their Relationship
In season 1's "The Stock Tip," Jerry made that hasty decision of taking Vanessa to a bed-and-breakfast in Vermont. Needleless to say, this vacation became a relationship killer and by the end, they couldn't stand being in the same room together.
It was Jerry who persuaded a reluctant Vanessa to go on a weekend trip with him. She said she was scared of trips that are taken too soon. He wanted to test their compatibility out and was eager to shift to phase two of the relationship. Ideally, Jerry and Vanessa should have waited a couple more months before taking that trip together. After all, haste makes waste.
When He Shared A Dry Cleaning Discount With Meryl Way Too Soon
Courteney Cox's Meryl was undoubtedly one of the best characters introduced in Seinfeld after season 1. She was smart as a whip and sharp as a tack. Meryl was seen in season 5's "The Wife," and played the titular character of Jerry's pretend-wife. Everything seemed to be going well in their relationship until Jerry shared his dry-cleaning discount with her. It ultimately sabotaged their pretend marriage because he wasn't ready to commit.
Jerry admitted to moving too fast and the two devolved into a cliched unhappy married couple. There's every chance that the relationship would have worked out well if Jerry had exercised caution against sharing such intimate things as discounts.