Seinfeld: Elaine’s 5 Best (And 5 Worst) Love Interests

One of the greatest sitcom icons of all time, Seinfeld’s Elaine Benes paved the way for promiscuous, freewheeling female characters like Liz Lemon and Broad City’s Abbi and Ilana. Every one of Elaine’s lines was delivered hysterically by Julia Louis-Dreyfus – when she wasn’t cracking up during takes (seriously, watch the show’s bloopers; she’s responsible for the lion’s share of them) – and her storylines were brilliantly written, drawn from the personal lives of such writers as Carol Leifer.

She had some fascinating love interests over the years, for better or for worse. So, here are Elaine’s 5 best, and 5 Worst, love interests.

10 Best: Keith Hernandez

In the two-part season 3 episode “The Boyfriend,” Jerry becomes friends with baseball player Keith Hernandez and experiences some confusing emotions as he begins to fall for him. Keith asks for Elaine’s number, so he can ask her out, and at first, Jerry is jealous of Keith, because he used to date Elaine.

But as the relationship develops, he becomes jealous of Elaine, because he has complicated feelings for Keith. When Keith starts using baseball terminology to flirt with Elaine, she tells him, “I’d watch the third-base coach if I were you, because I don’t think he’s waving you in.”

9 Worst: Phil Totola

Phil Totola is a guy that Jerry set Elaine up with. He claimed that Phil was the only guy he ever felt compelled to set her up with, because he thought they would be a good fit. And to be fair, they did have a good time together. After their date, they sat in Phil’s car, sharing stories and laughing hysterically.

But then, as Elaine would tell Jerry the following day, he “took it out.” This isn’t just horseplay or a cheeky move; it’s sexual harassment. Naturally, Elaine never wanted to see the guy again after this sordid incident, and it changed Jerry’s perspective of him, too.

8 Best: Aaron

In the two-part episode “The Raincoats,” Judge Reinhold guest-starred as Aaron, Elaine’s boyfriend who had little regard for personal space. Jerry termed him a “close-talker,” and was the only one who wouldn’t back down when Aaron came up close for a conversation.

It was a little strange that Aaron became obsessed with showing Jerry’s parents a good time while they were in New York, but it’s hardly a negative character trait. Aaron was aggressively nice. It ended up putting off Elaine, who found it to be too weird, but there are worse problems to have in a relationship than incessant niceness.

7 Worst: Owen March

As Jerry pointed out, Owen March was far too old to be dating twentysomething Elaine. The man was 66 years old – a senior citizen – with a heart so frail that when Elaine tried to break things off with him, he collapsed. And after he was hospitalized with a stroke and confined to a wheelchair, Elaine felt awkward going through with the breakup, so she kept seeing him and had to feed him soup.

The inappropriate age difference could be seen as a thematic link to a Woody Allen movie shooting on Jerry’s block at the center of the episode, but it was still uncomfortable.

6 Best: John F. Kennedy, Jr.

Season 4’s “The Contest” is widely regarded as the greatest episode of Seinfeld. (In fact, TV Guide has ranked it as the greatest TV episode ever made, period.) The premise revolves around the central quartet making a wager to see who can go the longest without masturbating, without actually using that word at any point in Larry David’s Emmy-winning script.

Each of the characters is faced with a test. For example, a nudist moves in across the street from Jerry. Elaine’s test is that John F. Kennedy, Jr. – who, she claims, has “a great butt” – joins her yoga class and takes a liking to her.

5 Worst: Dick

Dick is the recovering alcoholic that Elaine dated in the season 3 episode “The Red Dot.” The two worked together at Pendant Publishing, and at the office Christmas party, Jerry accidentally switched his booze for Dick’s cranberry juice, which ended up with him falling off the wagon.

Elaine would later accuse Jerry of doing this on purpose, but it did seem like an honest mistake. Even before he got back on the sauce, Dick was mean-spirited and spiteful. He was instantly standoffish with Jerry, angrily claiming to be funnier than him, and when he drank, he became violent on top of that.

4 Best: Jerry Seinfeld

Jerry and Elaine broke up years before Seinfeld began, but there was also a sense that they should’ve stayed together. Many Seinfeld fans expected them to profess their love for each other and get married in the series finale because that happens in every other sitcom.

And while that didn’t happen – during the Seinfeld finale, which threw the conventions of finale episodes out the window – Elaine did come close to confessing her love to Jerry as their plane was going down. In season 2’s “The Deal,” they tried to work out a “friends with benefits” situation and ended up just getting back together.

3 Worst: Fred Yerkes

Elaine was so irked that Fred didn’t remember meeting her that she became obsessed with him. He kept forgetting her name, and that made her desperate to date him, despite the fact that he’s really dull and boring, and he has a nasally, monotonous voice. She has to call off dinner plans with Jerry, George, and Peterman to make a date with him, and then he stands her up.

When she does finally get to have dinner with Fred, and he spends the whole time complaining about his mother, she realizes that Jerry was right and she was just attracted to him because he couldn’t remember her.

2 Best: David Puddy

Elaine and Puddy were like the anti-Ross and Rachel. They were an on-and-off couple in a ‘90s sitcom with a “will they or won’t they?” sort of vibe. However, where Friends fans wanted to see Ross and Rachel get together, Seinfeld fans could tell that Elaine and Puddy weren’t meant to be together.

They periodically rekindled their romance due to something trivial like Elaine having some furniture that needed moving. In one episode, they broke up and got back together several times over the course of a turbulent flight. Ultimately, though, Elaine and Puddy were both so terrible that they realized they wouldn’t find anyone better than each other.

1 Worst: “Crazy” Joe Davola

Although Elaine knew him as “Joey,” there was no mistaking “Crazy” Joe Davola. He was the psychopath who kicked Kramer in the head for not inviting him to his party and attempted to assassinate Jerry during the shooting of his sitcom pilot.

Lord knows how Elaine ended up dating him in the first place, but as soon as she found out he’d created a collage on the wall of his apartment filled with pictures he’d secretly taken of her from afar, she couldn’t wait to get out of there. As Joe tried to stop her from leaving, she pepper-sprayed him at the door.

About The Author

Ben Sherlock
(3486 Articles Published)

Ben Sherlock is a writer, comedian, independent filmmaker, and Burt Reynolds enthusiast. He writes lists for Screen Rant and features and reviews for Game Rant. He’s currently in pre-production on his first feature (and has been for a while, because filmmaking is expensive). You can catch him performing standup at odd pubs around the UK that will give him stage time. Previously, he wrote for Taste of Cinema, Comic Book Resources, and BabbleTop.

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