Seinfeld's Ultimate Girlfriend Fails: The Top 10 Trainwrecks!

Summary

Jerry's shallow and picky personality leads to short-lived relationships with most of the women he dates on Seinfeld.

Jerry's tendency to prioritize physical appearance over compatibility or emotional connection often leads to the failure of his relationships. He frequently sabotages these relationships due to his self-centered nature and refusal to compromise, resulting in absurd and ridiculous endings.

Throughout its nine seasons, Seinfeld delves into the complex love lives of all four main characters, with Jerry having the highest number of love interests. While he has a knack for attracting women, his selective nature and lack of boyfriend skills prevent any of these relationships from lasting. Across 180 episodes, Jerry Seinfeld dates a total of 73 women on the show, with most of them only making a single appearance.

For various reasons, Jerry's relationships tend to end quickly, often concluding by the end of their respective episodes. Only five relationships manage to extend beyond a single appearance. However, within the remaining 68 relationships, some prove to be worse than others. This is not to say that anything was inherently wrong with these women, but rather that they were not the right fit for Jerry. In certain cases, it becomes immediately evident that the foundation of the relationship is unstable right from the start, indicating a lack of compatibility.

10 Gillian

Better known by her cruel nickname of "Man Hands," Gillian, is introduced to Jerry by Elaine in Seinfeld season 8, episode 3, titled "The Bizarro Jerry." Although they initially hit it off, Jerry becomes fixated on the muscular nature of Gillian's hands. This surface-level concern is just one example of Jerry's shallowness negatively affecting a relationship. Furthermore, Gillian inadvertently injures Jerry while trying to prevent him from snooping through her purse. While Gillian seems to possess kindness, she struggles to thrive in Jerry Seinfeld's merciless world.

9 Alex

In season 8, episode 21 of "The Muffin Tops," Jerry inadvertently shaves off his chest hair. Initially regretful, he discovers that Alex actually prefers smooth-skinned pets. Instead of admitting his preference for a hairy chest, Jerry chooses to maintain the charade. Consequently, he leads a deceptive existence, surreptitiously scratching his itchy chest behind her back. While in this relationship, Jerry assumes a false identity and subjects himself to discomfort. Although entirely self-inflicted, this situation exposes the shallowness of their connection, with Jerry altering his body for virtually no legitimate reason.

8 Katya

7 Pam

Jerry's dating preferences are predominantly based on shallow criteria. Rather than valuing a person's personality, he is primarily drawn to them based on sexual attraction. In season 6, episode 6 titled "The Gymnast," his relationship with Katya exemplifies the negative impact of this superficial approach. Despite her clear stance against casual sex, Jerry's sole interest in her stems from her gymnastics background. Consequently, he feigns romantic interest to solely fulfill his desire for physical intimacy. Eventually, their sexual encounter proves disappointing for both parties, leading to the end of their relationship. This scenario demonstrates how two individuals pretend to be interested in each other, but only for their anticipated personal benefits.

In the opening of Seinfeld's eighth season, in episode 2 titled "The Soul Mate," Jerry finds himself in what appears to be a healthy relationship. However, after dating Pam for a while and not feeling any real connection, he decides it's time to call it quits. But when Kramer becomes infatuated with her, Jerry suddenly starts questioning his own feelings and wonders if he might be in love with Pam after all. This competition between Jerry and Kramer intensifies to the point where they both consider getting vasectomies as a way to prove their love for Pam. Jerry becomes consumed with thoughts of a woman he isn't even certain he truly likes. Fortunately, he eventually realizes the absurdity of the situation before it's too late.

6 Audrey

Audrey, who makes her debut in season 5, episode 15 titled "The Pie," proves to be an absolute nightmare as Jerry Seinfeld's girlfriend. Being a stickler for cleanliness and overly concerned with the nuances of social interactions, Jerry finds himself in quite the predicament with Audrey. In sharp contrast, Audrey is a private individual whose unhygienic chef father never bothers to wash his hands after using the restroom. Jerry becomes fixated on Audrey's refusal to explain why she won't try his pie, and this incident becomes an insurmountable obstacle for him. His obsession over this trivial matter prevents him from delving deeper into their relationship, ultimately causing their demise. Clearly, this is a romantic connection that can't even withstand the tension over dessert.

5 Naomi

In Seinfeld season 4, Jerry gives Naomi, his girlfriend, the unflattering nickname "Elmer Fudd" due to her peculiar laugh. When Naomi discovers this in season 4, episode 7, "The Bubble Boy," she rightfully ends their planned trip. Interestingly, Naomi exhibits a similar shallowness to Jerry by accepting Kramer as her travel companion instead. Jerry, being a comedian who values humor above all else, finds an annoying laugh to be a dealbreaker in his relationships.

4 Marla

Compared to most Seinfeld girlfriends, Marla managed to maintain a relatively longer presence on the show, appearing in two episodes before the predictable demise of the relationship. During her time with Jerry, she was depicted as a virgin, and initially, Jerry displayed an uncharacteristic level of maturity about this situation. However, things took a turn for the worse when he engaged in Seinfeld's infamous masturbation contest with his friends in season 4, episode 10. Ultimately, this contest became the breaking point in their relationship, as Marla was utterly repulsed by the idea. Marla's innocence and lack of familiarity with Jerry's sexual deviancy became a significant obstacle. Their contrasting lifestyles and incompatible perspectives raise doubts about how they ever believed their relationship could succeed.

3 Sheila

Jerry's relationship with Sheila is considered the worst by George and Elaine. In Seinfeld season 7, episode 6, titled "The Soup Nazi," Jerry and Sheila affectionately call each other "Schmoopie" but their excessive public displays of affection make everyone uncomfortable. However, Jerry's true intentions are revealed when he prioritizes a cup of soup from the Soup Nazi over his passion for Sheila. Jerry always puts himself first, making it impossible for any girl who values affection over his desires to succeed.

2 Dolores

In Seinfeld season four, episode 21, "The Junior Mint," Jerry embarks on a romantic relationship with an enchanting and stunning woman. However, he hits a roadblock as he struggles to recall her name. Rather than confessing his memory lapse, Jerry endeavors to uncover her name covertly, fearing her discovery of his forgetfulness. Unsurprisingly, Jerry's endeavors end in disaster, leading Dolores, one of his most affable exes on the show, to end their relationship upon realizing his childish behavior. Dolores, a self-assured and mature woman, finds Jerry's immature antics incompatible with her character. Even upon reconnection in subsequent seasons, Dolores turns down Jerry, indicating that he has yet to mature.

1 Marlene

Prior to becoming Jerry's girlfriend, Marlene had previously dated George. Despite being aware of the qualities that bothered George about her, Jerry impulsively dives into a romantic relationship with her in Seinfeld season 2, episode 1, titled "The Ex-Girlfriend." Remarkably, the same issues that irked George also begin to annoy Jerry. However, things take a turn for the worse when Marlene witnesses Jerry's comedy act and realizes that she lacks respect for his chosen profession. While Jerry has a track record of sabotaging relationships, this particular one should have been avoided altogether. He overlooks every warning sign and disregards his friend's emotions simply because he is physically attracted to Marlene. Neither Jerry nor Marlene possess any mutual respect for one another, or even for George, which ultimately makes their relationship the absolute worst showcased on the show.