Elaine’s Worst Boyfriends on ‘Seinfeld,’ According to Reddit

Elaine is almost as good at picking boyfriends as she is at dancing
Elaine’s Worst Boyfriends on ‘Seinfeld,’ According to Reddit

The fans over on the r/Seinfeld subreddit are at it again, arguing over who was Elaine’s worst boyfriend. It’s hard to count up which of her several flawed paramours scored the most upvotes due to an overly long thread featuring several duplicate suggestions, but here are seven idiots who are at least in the running for the title. Elaine Benes, you deserved better than all of them. 

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Phil Totola

The thread starts with a picture of shocked Elaine looking down at Phil’s lap and you can probably guess what’s going on by her reaction. When Jerry asks how the date went (he set her up with Phil in the first place), Elaine gets right to the point: “He took it out.”

So yeah, sexual harasser Phil makes the list. The rest of the Seinfeld gang doesn’t come off too well either. At least Jerry is shocked. But as u/certifiedbpdqueen writes, “Kramer defends Phil, and says, ‘Well maybe it needed to breathe,’ and George is amazed at why he never thought of doing it before.”

Crazy Joe Davola

There’s “crazy” as in “that guy painted his face blue for the football game!” And then there’s “Crazy Joe Davola crazy.” Joe seems genuinely mentally ill, and everyone is justifiably frightened of what he will do next. And so, is it really that funny when Elaine shows up at his apartment and finds a wall of Elaine pictures, including ones of her showering, taken secretly with a telephoto lens?


Elaine is distrustful of her new boyfriend Glenn, suspecting he might be married because he won’t give up his phone number. Turns out that he’s just poor, which might be even worse. (As Elaine will eventually find out, Glenn is both poor and married.)

Jake Jarmel

Jarmel got multiple nominations because he’s “a pretentious prick” (u/Kman_24), and “she’s had multiple spats with him” (u/crudeyakuza). Even worse in Elaine’s book? When Jake takes a message about her friend’s new baby and makes questionable use of available punctuation (“Maybe I don’t use my exclamation points as haphazardly as you do”), she has to end the relationship.  

Todd Gack

Does Todd Gack actually qualify as a boyfriend? He never actually asks Elaine out, after all, managing to get a dinner date by losing a stupid bet (turns out, Dustin Hoffman wasn’t in Star Wars) and having to pay up. The deal breaker: He shows up on their second date with his parents. 

Castle Rock Entertainment

Dr. Reston

Perhaps the reason Crazy Joe Davola was so crazy was that he had the unprofessional Dr. Reston as his therapist. He was also Elaine’s doctor, which is… problematic.  “Aside from being creepy looking,” says u/jefferson497, “he is also highly unethical and manipulative.” Despite those terrible qualities, Elaine goes to Europe with Reston. But she’s so afraid of the powerful hold he has on her that she calls it off by pretending to be Kramer’s girlfriend. Reston befriends Kramer and convinces him to help win Elaine back. 

Manipulative, indeed! 

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