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Seinfeld: Jerry's 5 Best (& 5 Worst) Relationships

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Even now, twenty years removed from the series ending, there still hasn’t been a sitcom like Seinfeld. For nine years, Jerry and his friends were a quartet of deliverance for the rest of the world. There has been much ballyhoo over the years made about the series was a “show about nothing.” There must have been a serious amount nothing going on - show ran for 180 episodes, has reoccurring characters and storylines and to this day exists in reruns in perpetuity.

At the time Seinfeld debuted, all the leads on a show being single was a rarity. It made for a ton of entertaining relationships that Jerry, Elaine, George, and Kramer all had. It must’ve been nice for co-creator, writer, and star Jerry Seinfeld to script and cast the character of Jerry’s seemingly never-ending string of girlfriends. Whether he cast models, actresses, or fellow comediennes, here are Jerry's 5 Best (& 5 Worst) Relationships.

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10 Best - Elaine, “The Deal”

While they claim that they worked better as friends, throughout the entire series it was painfully obvious to everyone in the show and watching it that these two were made for each other. While they dated before the show started, they only officially dated for the briefest moments in the season two finale, “The Deal,” which is enough to count Elaine as a girlfriend. Their conversation about how to be friends and sleep together is one for the ages and when it end with Jerry realizes he needs to be with her would be the perfect ending for a romcom, but this was Seinfeld, by next season their relationship was over.

9 Worst - Marlene “The Ex-Girlfriend”

Jerry and George are both a bunch of masochists. At separate points on the show, they’ve both shown an attraction towards a woman who is either mean to them or doesn’t find them attractive. In “The Ex-Girlfriend,” Jerry starts dating George’s ex, Marlene. He eventually finds her as annoying as George did. But it isn’t until she sees him perform that she actually breaks up with him. She can’t be with someone that she doesn’t respect, and not finding a professional funnyman funny is pretty disrespectful.

8 Best - Jeannie “The Invitations” / “The Foundation”

When you save someone’s life, the least they should do is take you out for coffee. Which is what Jerry does when he meets Jeannie Steinman - “hey same initials!” Jerry’s instantly smitten, and they soon realize they’re pretty much the same person.

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They both like making random inane observations about the mundane and eat cereal for dinner. Jerry loves “himself” so much that he even proposes to Jeannie, who says “yes.” But by the next episode, they decide to end things in the most perfect break-up ever, mutually and comically blurting out “I hate you.”

7 Worst - Audrey “The Pie”

Who doesn’t like pie?! Much worse, who would actually date someone who didn’t eat pie? It’s decidedly unpatriotic in any culture. While Jerry is too neurotic to let this fact go about Audrey; it IS a fact. Then again, when you’re dad owns a restaurant and doesn’t wash his hands in the bathroom, could you really blame her for not wanting to eat anything from a restaurant?!

6 Best - Meryl “The Wife”

Played by FriendsCourtney Cox, Meryl and Jerry enjoyed pretending to husband and wife. If you’ve ever pretended to be married to your boyfriend or girlfriend, then you know it’s cute and fun and silly - just like Meryl. Jerry’s having a ball saying, “my wife this,” and “my wife that.” They share pancake secrets at the diner and Meryl gets to use Jerry’s Dry-Cleaning discount. Problems arise when Jerry decides to play the same game with another girl and in typical Seinfeld fashion, that’s the end of Meryl.

5 Worst - Gennice “The Understudy”

Actors love to act, understudies love to overact just to compensate, in theory. But Gennice was just a weirdo all around. Her beloved grandma dies, she doesn’t seem to care. George inadvertently cripples Bette Midler, leaving the door open for Gennice to star in “Rochelle, Rochelle,” bupkiss from her emotionally. She drops a hot dog on the floor - inconsolable. Gennice was the worst, Jerry. The worst.

4 Best - Sidra “The Implant”

From eighties B-movie star to a desperate housewife and Lois Lane in between, you’ll be hard-pressed to find someone who doesn’t enjoy Teri Hatcher for one reason or another. She even made her way over to Seinfeld, as his girlfriend Sidra in one of the top-ten episodes, “The Implant.”

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Elaine and Jerry argue over the validity of Sidra’s... um... mammary glands. Elaine inadvertently (?) gets a gander at them and proclaims they’re real (after Jerry already broke it off with her because he thought she was false-advertising). But as any fan knows - “they’re real and they’re spectacular.”

3 Worst - Isabel “The Nose Job”

Tawny Kitaen guest starred as Isabel in “The Nose Job.” Jerry’s brain knew she wasn’t worth the time, but other parts of Jerry disagreed and found Isabel to be quite alluring. It was a game of chess for Jerry as he tried to weigh the options of dating someone insanely beautiful but nowhere near as beautiful on the inside as she is outside. He’s doing his best to deal with it, until the aspiring actress with no talent wants Jerry to read lines with her.

2 Best - Lois “The Race”

Both real and TV Jerry have a huge affinity for Superman. They both must have been tickled to be dating a woman actually named Lois in the sixth season Christmas episode, “The Race.” It definitely led for some awesome Man Of Steel-inspired moments. It turns out that Lois works for one of Jerry’s old rivals. Now he has to prove that he’s faster than a speeding bullet; or at least her boss, Duncan, otherwise he’s going to fire Lois.

1 Worst - Donna “The Phone Message”

Jerry is dating quite possibly the most vapid and self-conscious woman on the planet. Her name is Donna and as far as the show in concerned, her two character traits is that she loves a Dockers commercial, thinking it’s hysterical. The other trait is being so self-conscious that she breaks up with Jerry when he doesn’t understand why she likes it and when he tells George and Kramer about it.

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