Many people consider Seinfeld a comedy, but they’re wrong. Despite its masturbation wagers, yodeling belly buttons, Newmania, and other hilarious moments, the show was clearly a work of fantasy. How else could an unemployed, hipster doofus afford his own Manhattan apartment? How else could Jerry pay for all that stone-washed denim while slinging Ovaltine jokes? How else could Elaine never have anything better to do? And most fantastical of all: How did George Costanza get dates with all those beautiful women?
The fine folks at Kramer’s Apartment have tallied that George hooked up with a credulity-straining, reality-shattering, brain-cramping 47 women over the course of the show. 47 women! How many of your friends have hooked up with 47 women (and most of them gorgeous with feathered hair, no less) in a nine-year period? Now how many of those gentlemen also happen to be stumpy, chubby, balding, rage-filled, perpetually unemployed, emotionally immature, lazy, garbage-pastry-eating misanthropes?
But even the best fantasy still has to be grounded by the harsh weight of reality — from parent murder in Harry Potter to boiling sexual tension in Lord of the Rings — and Seinfeld is no exception. Because even though George has dated some of the most beautiful women in Manhattan, his personality ensures that every single one of these relationships ends in failure, humiliation, and the occasional glue poisoning. Here are his 10 most devastating breakups.
#10. Susan Ross — Season 4 and 7
While not technically a breakup, George inadvertently (and fatally) poisoned his fiancee with toxic glue from bargain wedding-invitation envelopes, ending the relationship before his personality could finish the job. The sudden death of a loved one would haunt most people, but for George, it provided only a brief moment of reflection that was quickly replaced by a desire for coffee.
#9. Karen — “The Mango,” “The Masseuse”
When a balding, overweight, and underemployed man manages to have sex with a beautiful woman, his response is typically gratitude. But in “The Mango,” George is so insecure about his boudoir performance that he not only doubts the authenticity of his girlfriend Karen’s (future House star Lisa Edelstein) orgasm, he outright mocks her attempts at “faking it.” Amazingly, she only kicked him out of bed and did not immediately end the relationship.
That did not happen until eight episodes later in “The Masseuse.”
#8. Anna — “The Little Kicks”
George Costanza is simultaneously one of the best and worst liars in television history. He’s the best because of the way he crafts these elaborate tapestries of deception that can convince people that he is anything from an accomplished architect to a marine biologist. But he’s also the worst, because his lies always end in disaster. Like the time he got chased by gangs of aggressive senior citizens. But of all George’s lies, convincing Elaine’s beautiful employee Anna (Rebecca McFarland) that he was an irresistible bad boy was perhaps his most impressive. The eventual unraveling of that lie, with George weeping in a police station after an attempted movie-theater bootlegging, was also impressively humiliating.
#7. Bonnie — “The Label Maker”
A three-way is a sexual fantasy for most men. For George Costanza, it is his “break glass in case of emergency” method to get out of a relationship. But as Bonnie (Jessica Tuck) and her Costanza-doppelganger roommate, Scott (Cleto Augusto), proved in “The Label Maker,” in the high-stakes game of erotic poker, eventually, someone will call your bluff.
#6 Lindsay — “The Gymnast”
It’s always sad when the extended family of a loved one interferes in a new relationship and smothers the spark of romance. However, it’s significantly less tragic when the interfering and smothering is done for the justifiable reason of seeing your daughter’s boyfriend eating trash pastries.
#5 Sheila — “The Package”
Many women have been willing to overlook George’s many flaws for his few, but shining qualities —Frogger mastery, pastrami appreciation, and toilet sherpa-ing to name a few. But even the most forgiving woman has her limits, and as Sheila (Heather Campbell) proved in “The Package,” that limit begins with abandoning women, children, and clowns in a burning building.
#4 Maura and Loretta — “The Strongbox”
George Costanza is accustomed to failure — unfulfilled dreams, crushing mediocrity, being denied soup — but he is excellent at ending relationships. However, in “The Strongbox,” George loses even this ability when his girlfriend, as well as the sidepiece he “accidentally” parades in front of her to destroy the relationship, both refuse to leave him. Of course, why two women (no matter how orange) would agree to share a man like George, is a mystery that rivals the “magic loogie.”
#3: Janet — “The Cartoon”
Janet (Tracy Nelson) had everything George ever thought he wanted in a woman — beauty, a pulse, a tolerance for his naked body — as well as one irresistible trait he did not notice until Kramer pointed it out to him: She looks exactly like Jerry. But rather than confronting his latent attraction to Jerry, or numbing those feelings, George instead blew up his relationship with Janet rather than try to “have everything I have with Jerry, but because it’s a woman, I could also have sex with her, and that somehow that would be exactly what I’ve always wanted…”
#2: Marisa Tomei — The Cadillac
To be clear, George never dated Marisa Tomei, and the closest he made to any romantic contact with her were amorous advances to a throw pillow. In fact, it appears the only time they ever touched was when her knuckles cracked his man-turtle chin.
#1. Jane — “The Hamptons”
Despite all the cowardice, immaturity, violence, gay panic, regular panic, and death, the fallout from the “frightened turtle” incident in “The Hamptons” is, and without any real competition, the most devastating and humiliating breakup in George “T Bone” Costanza’s life. Because there is no torture more ego-shredding, devastating, and cruel than a group of women gossiping about your dangling thumb. Despite his many sins, George did not deserve this caliber of cosmic punishment.