While the gang in Seinfeld have gone through their ordeals and messy mishaps, some of them don’t compare to their individual mishaps with their exes. While Jerry has his slew of unfavorable ex-girlfriends, Elaine also has her fair share of exes that rank from being a great catch to not worth a second call.
Many can recall Elaine’s ex, Dick who fell off the wagon when he accidentally drinks Elaine’s vodka-cranberry. He wasn’t so well-liked and had an anger problem. Alas, some past exes are deemed worthy on the nice scale and weren’t that bad but still had their flaws.
Dr.Reston made his appearance in season four of the show. He was played by actor Stephen McHattie. His and Elaine’s relationship was a bit odd. While the psychiatrist had a formidable career, he wasn’t the best boyfriend. This was mostly due to his inability to separate himself from the job.
While on vacation in Europe, he can’t help but fret over one of his patients. Elaine ends up calling him her “Svengali” for having a mental hold on her. Even in his office, he treats her more like a patient than a love interest. When she tries to break it off by having Kramer pose as her boyfriend, Reston manipulates Kramer to be on his side.
9 Jerry Seinfeld
One of Eliane’s more infamous ex-boyfriends is Jerry. But audiences never actually get to see them date in the show. It’s already a past relationship that fizzled. Knowing Jerry’s character, one can say that he was probably not one of Elaine’s best exes. He tends to be self-absorbed and think more for himself.
It’s unlikely that he was ever romantic or deeply interested in Elaine’s interests. In an episode, Elaine even admits that she faked her sexual climax when she was with him. Throughout the show, it’s clear that they’re better off as friends.
8 The Maestro
The Maestro (Mark Metcalf) isn’t as bad of an ex as one might think. He’s a minor side character that makes multiple appearances in the show. Overall, he’s not a bad ex-boyfriend. He even takes Elaine on a trip to Tuscany to his villa. He’s also a conductor and lover of classical music. But he does have his flaws.
Maestro is a bit insecure about himself and prefers everyone to call him maestro instead of his real name. While getting hot and heavy, Elaine accidentally calls him Bob but quickly corrects herself when he gives her a look. After their breakup, the two remain on good terms. Elaine even gets a signed poster of the other tenor for him.
When analyzing Aaron (Judge Reinhold), many would think he’s an overall swell guy. Many of Elaine’s coworkers find him to be incredibly sweet and polite. But he does have one bad habit. He’s a “close-talker.” He will start speaking to anyone while invading their personal bubble.
One can say that besides that Aaron is very passionate but a bit excessive. He’s kind enough to offer Jerry’s parents a fun tour of New York. Seeing as Jerry refuses to do anything with them. He shows them the Met, takes them to My Fair Lady and a lavish dinner. By the end, he does get distraught over thinking he could’ve done more.
6 Jake Jarmel
Jake Jarmel (Marty Rackham) is both a good ex but also a bad one when he makes a not so favorable impression in ” The Scofflaw.” At first, Jarmel is a good boyfriend who really doesn’t do anything wrong in the relationship. He even cleans up Elaine’s apartment and makes dinner. Elaine even calls him perfect. But when he doesn’t add an exclamation point on a phone message, Elaine gets upset.
Jarmel then breaks up with her again when she buys JuJu Fruit before rushing to see him after his accident. By his last appearance, Jarmel is bitter towards Elaine and ends up being childish towards her because she wants to know where he got his glasses.
While Elaine and Tony’s (Dan Cortese) relationship might have been superficial, Tony isn’t so bad. While there’s a clear age difference that leads to different interests, Tony is genuinely nice. Jerry thinks Elaine only cares about Tony’s good looks.
In “The Stall,” Tony is more than happy to chat with Geroge and Elaine’s friends. He even invites George and Kramer to go rock-climbing. He might be a bit of himbo to Jerry but Tony was one of Elaine’s exes that was a good catch. Elaine ultimately breaks up with him for fear of his accident having caused him to no longer be handsome.
4 Joel Rifkin
In “The Masseuse,” Elaine starts dating Joel Rifkin (Anthony Cistaro). The problem is that he shares the same name as the notorious serial killer. This puts a damper on their relationship. Besides the name issue, Rifkin isn’t all that bad of a guy. He’s incredibly sweet and caring with Eliane.
Elaine just finds his name to be a problem. Elaine and Joel even offer Kramer a free ticket to a football game. Seeing that his name causes such an issue, Rifkin ponders Elaine’s idea of legally changing it. They even have a whole session in her apartment trying to choose a new name.
Billy (Scott Patterson) is only seen in the highly popular and comical episode, “The Sponge.” It’s the episode where Elaine’s contraceptive of choice is discontinued and she goes on a hunt to get as many as she can. Billy is handsome, caring, and one of Elaine’s better exes. He’s played by actor Scott Patterson.
In the episode, Billy has to prove himself sponge-worthy seeing as Elaine has to be choosy on who she has intercourse with. Taking a look at Billy as a boyfriend, he’s not bad. He was willing to prove his case on why he was sponge worthy. He owns a successful electronics distributing firm, exercises, and is perfectly healthy. Billy was also willing to shave his sideburns.
2 Hal Kitzmiller
Hal Kitzmiller (Vince Grant) is actually one of the rare few who was 100% genuinely nice but ends up not being right for Elaine. In “The Nap” Hal suffers from back pain when he starts dating Elaine. Worried for Elaine, he takes initiative to buy her the best mattress on the market.
When she receives the mattress from The Lumber Yard, Elaine initially takes offense. She thinks it’s his way of getting her in bed. In reality, he was just worried about her back. It was even specially made for her. When Kramer makes a vague remark about being in her bed, Hal gets jealous until he realizes nothing is going on between them.
1 David Puddy
Puddy (Patrick Warburton) is one of Elaine’s boyfriends that sticks around for much of the show. They have an on-again-of-again relationship. It can sometimes even turn messy. While Puddy may not be the sharpest tool in the shed, he proved to be a swell boyfriend.
Despite him having multiple qualities that Elaine detests, he oftentimes isn’t so bad. Elaine was bothered by his face paint and said he wouldn’t do it anymore. Instead opting for body paint. He becomes a highly favorable side character for his goofy demeanor and his ongoing role in the show.