NBC’s hit television show Seinfeld featured 66 different love interests for lead actor Jerry Seinfeld over its nine-season run. Many of Jerry’s paramours have gone on to become well-known Hollywood celebrities. Anna Gunn, who won two Emmy Awards for her role as Skyler White in AMC’s Breaking Bad made an appearance as Amy in season 5's “The Glasses.” Courteney Cox also appeared in a season 5 episode as his girlfriend Meryl, six months before another NBC monster-hit show, Friends, premiered.
How did Jerry end the show still a bachelor? His obsessive, nit-picky personality may have had something to do with it. Who were the top five he let get away but shouldn’t have? And who were the top five where he dodged bullets?
Would Date: Elaine
S2E9 - "The Deal" - Chronologically, Elaine Benes and Jerry were romantically involved (and done) before the start of the series. Their chemistry is great, so it's unsurprising that Julia Louis Dreyfus was cast as Elaine after the series pilot aired. But early on in its run, NBC applied pressure to get them together again. This episode was co-writer Larry David’s response. Jerry and Elaine craft a shaky friends-with-benefits deal after stumbling upon some soft-core porn on television and begin sleeping together.
The longer it goes on, the trickier it becomes for them to navigate the rules. Elaine’s birthday becomes the litmus test that Jerry inevitably fails, settling on a cash gift after rejecting more meaningful options. Keeping them apart was the right choice for the series, but Elaine is definitely a keeper.
Wouldn't Date: Angela
S3E20 - "The Good Samaritan" - While driving, Jerry witnesses a hit-and-run car accident while on the phone with Elaine. She convinces Jerry to follow the driver, who turns out to be a knockout. Angela’s (Melinda McGraw) good looks leave Jerry so smitten and tongue-tied he doesn’t confront her but begins to date her instead.
Jerry tries to bring the issue up in roundabout ways during their steamy makeout sessions. Eventually, he confronts her about it, and a psychotic side of Angela erupts - “You tell anybody anything and I will carve my initials in your brain tissue.”
Would Date: Rachel
"The Raincoats" (S5E18 & 19); "The Hamptons" (S5E21); and "The Opposite" (S5E22) - Melanie Smith plays Jerry’s second-most (to Elaine) dated girlfriend, Rachel Goldstein. In “Raincoats,” having not seen in each other in a while, Rachel makes out with Jerry through an entire screening of Schindler’s List, observed by Jerry’s frenemy, Newman. He gleefully reports the transgression to Jerry’s parents and Rachel’s father, who are all horrified.
In “The Hamptons,” Rachel accidentally observes a naked George Costanza changing clothes after a swim in a cold pool. “Shrinkage!” George yells in his defense. In “The Opposite,” Rachel breaks up with Jerry, who is completely unfazed because of his run of “even-Steven” luck.
Wouldn't Date: Jenna
S8E16 - "The Pothole" - Kristin Davis guest-starred as Jenna in this episode the year before she landed the role of Charlotte in Sex and the City. Jerry reveals that he accidentally dropped Jenna’s toothbrush in the toilet -- but only after she’s already used it. Infuriated, she disappears to the bathroom and then tells him, “There. Now, something of yours has been in the toilet.”
Deliberately leaving the object unnamed is the perfect revenge against neurotic Jerry. Yes, he should have confessed immediately. But two wrongs never make a right. Right?
Would Date: Jeannie
S7E24 - "The Invitations" - Jeannie Steinman, played by comedian Jeanine Garafolo, is one of Seinfeld’s funniest love interests. Jerry falls for Jeannie after she pulls him out of the way of an oncoming car on the street. Jerry explains to Kramer:
“This woman is different. She’s incredible. She's just like me. She talks like me, she acts like me, she even orders cereal in a restaurant. We even have the same initials! Wait a minute ... I just realized what's going on. Now I know what I've been looking for all these years: myself! I've been waiting for me to come along and now I've swept myself off my feet!”
Garafolo basically does a Seinfeld impression for the episode, as Jerry slowly concludes that there’s only room for one Jerry in his life. She might not be for Jerry, but who wouldn’t love to date a pretty, observant, funny woman?
Wouldn't Date: Delores
S4E20 - "The Junior Mint" - Jerry confesses to George that he can’t remember the name of a woman he started dating after having met in a grocery store. He's afraid to ask her because they’ve already kissed. Jerry susses out a clue - her name rhymes with a female body part. It’s not enough, and of course, she catches on and forces him to guess her name" "Mulva? Gipple? Loreola!?"
Only after she storms out does Jerry finally remember and screams out the window: "Delores!" It’s okay to let this one go, Jerry. You need someone who would find it as funny as we do.
Would Date: Ellen
S8E14 - "The Van Buren Boys" - Ellen is played by Christine Taylor (married to Ben Stiller, with whom she co-stars in Zoolander and DodgeBall: A True Underdog Story).
Ellen has no discernible faults, but she unsettles Jerry. He's certain that there must be something wrong that he just can’t see. He calls it all off after Jerry’s parents meet Ellen and love her immediately.
Wouldn't Date: Sheila
S7E6 - "The Soup Nazi" - This episode is better remembered for Larry Thomas’s portrayal The Soup Nazi than for Alexandra Wentworth’s saccharine-sweet portrayal of Sheila, Jerry’s overly-fawning, cutesy girlfriend. They sicken everyone around them with their baby talk and their public displays of affection.
The plotlines come together brilliantly when The Soup Nazi denies Sheila soup for kissing Jerry while waiting in the queue. Jerry must choose between the best soup in the city and Sheila. “Do I know you?”
Would Date: Sidra
S4E19 - "The Implant" - The comedy-of-errors episode, featuring Teri Hatcher as Sidra, aired shortly before Hatcher was cast as Lois Lane in ABC’s Lois & Clark: The New Adventures of Superman. Early in the episode, Jerry breaks up with Sidra because he suspects she has breast implants. Later, Elaine encounters Sidra in a sauna and slips, making a fumbling grab at Sidra's towel. She leaves convinced that Sidra is packing the real deal, and reports this to Jerry, who then reverses course on the relationship.
Later, when Sidra suspects that Jerry set up Elaine’s towel grab, she breaks it off with one of the most-quoted lines of the series: “And by the way, they’re real. And they’re spectacular.”
Wouldn’t Date: Jane
S5E12 - "The Stall" - Jerry's girlfriend Jane, played by Jami Gertz, and Elaine have an encounter in side-by-side stalls in a movie theater restroom, where Jane denies Elaine’s desperate pleas for a spare square of toilet paper after she discovers her own stall is empty.
They depart without knowing the other’s identity, but Jane's voice is etched in Elaine's memory. Elaine gets her revenge at the diner by the end of the episode. Really, if you can't spare a square for a stranger, how generous can you be in a relationship?