Women that Seinfeld Should’ve Dated

Who could forget the classic Seinfeld episode where Janeane Garofalo comes on the show and rocks Jerry’s superman-and-cereal-invested world?

Lane Cummingsby Lane Cummings

Seinfeld had some notable girlfriends on the show—Teri Hatcher, AJ Langer, Courtney Cox, Celeste, and others. But think of all the ladies that never made it on the show and the ballyhoo that we viewers missed. 

Sandra Bernhard

Now that would’ve been a winning episode. Sandra’s character would’ve heckled Jerry at one of his shows. He would’ve come up with a snappy (but not biting or R-rated) remark back. She would have told him to suck her d*ck, and somehow they would’ve wound up in the sack. You can picture it, Jerry sitting across from George at the diner (or course) both on their designated sides of the booth (George with his back to the door), as Jerry fills George in about the wild stuff Sandra treated him to the other night. Sandra would’ve met George and ripped him in two. Elaine would’ve found that hilarious until Sandra started hitting on her. And just when you think the episode is going to turn into a rerun of that episode where Jerry almost has a threesome, Jerry would’ve broken up with her because he found her lips “too much”. George would’ve added that she scrunches her face up like a piece of dehydrated fruit, proclaiming, "Who wants to date a raisin?"

Winona Ryder

This would’ve been awesome. Because Winona would’ve played nicey-nice with Jerry for a while, hiding the pompous hipster that she really is, biding her time. They would’ve met in a coffee house, a la Reality Bites (perhaps Jerry was there because the diner was shut. I don't know). He would’ve said something random, (what’s the deal with all these artificial sweeteners?) she would faked a laugh for him and they would’ve gone out. Started dating. And just as it got serious, Jerry would notice something missing from his apartment, like his can opener. And just as you, viewer, thought that it was going to be a rerun of that who-took-the-raisins episode, full of speculation and what-have-you, Elaine would catch Wino going through her purse, out to steal something equally random, like Elaine’s cherry binaca. And little Elaine would’ve schooled that ho.

Meg Ryan

Who the heck knows or cares how Jerry would’ve met Miss Meg. But they would’ve hit it off right away. And just as Elaine, Kramer and George started celebrating that Jerry was finally going to have a relationship longer than two weeks to a real, true normal person, Jerry would’ve found fault with Miss Meg, because that's how he gets his jollies. If the show took place in the nineties, he would’ve complained that she was too fresh-faced, or too neat, making his role in the relationship irrelevant. If the show took place, say now, he would’ve said that she jacks her face up with too many fillers and reminds him of the love child of Elmer Fudd (on a juicer—someone out there gets it) and Renee Zellweger.

Jennifer Aniston

Hey, I had to put her on the list because Jennifer's BFF, Courtney Cox, was once on the show, playing the girlfriend that Jerry pretended was his wife so she could get a dry–cleaning discount at the place round the corner. Just writing that here and now makes me shake my head, (but with wonder) at how ridiculous (but painfully beautiful) some of the plot points of that show were.  Jennifer could appear on the show as the girlfriend that does everything right—laughs at his jokes, remembers his birthday, doesn’t annoy him. However, she would be the one that would demand a real relationship and real commitment. Something that the superman-comic-book-reading-cereal-eating-Jerry is hardly ready for. In fact, her character might burst into tears once he tells her “Uh, I don’t think so” in response to her commitment demands, and Jerry would be forced to see a human emotion not based on hardy-hars or pithy remarks. But we can all probably count on that he’d just say, “Aw, that’s a shame.”