Elaine’s Best Boyfriends on ‘Seinfeld’

The best and definitely not brightest men Elaine Benes ever bedded
Elaine’s Best Boyfriends on ‘Seinfeld’

The pay gap between male and female actors is one of the most oft-discussed topics in entertainment, but when it comes to the seminal sitcom Seinfeld, we must not forget another important discussion in gender discourse — the lay gap.

The retrospective treatment of Seinfeld among today’s terminally online inevitably leads fans to the same tired conversation topics and ranking material of which of the dozens upon dozens of gorgeous women dated by Jerry and George over the course of the show’s nine seasons is the “best,” or the “hottest,” or the most “underrated.” The show’s title character had a total of 73 girlfriends and flings during the duration of Seinfeld, with the short, stocky, bald Costanza coming in with a body count of 47 lady loves, living or dead. That totals to 120 women whom male Seinfeld fans can compare, rank and rate endlessly in online forums until their live-in parents come home.

Rarely, however, are Elaine Benes’ beaus similarly appraised. One user in the Seinfeld subreddit took umbrage with this lack of shallow evaluation, challenging Seinfeld fans to list their picks for Elaine’s “best” boyfriend. With a give-or-take total of 50 on-and-off-screen companions to compare, here are the top entries…


Sure, Ton-ay may have been a mimbo. Yes, he was almost definitely too young for a fully grown woman like Elaine to be smashing. And, sure, the only reason she ever dated him was because of his long, luscious locks, his hip 1990s digs and his beautiful bone structure. But, man, Tony was cool! He wore a backwards hat! He popped his collar! He tells people to “step off!” What’s there not to like?

Unfortunately, George was significantly more infatuated with Tony than Elaine herself, and, as Susan’s ghost can attest, George’s affections often lead to grim consequences — like a face full of bandages that make Elaine lose interest.

Jerry Seinfeld

Of course, Elaine’s most present sexual partner is an obligatory entry on the list, even though we never saw the former couple in the prime of their romance. The length of their relationship is never properly defined — other than the fact that they had sex either 37 or 25 times — but their extended platonic partnership (plus a little extra in Season Two) shows that Jerry and Elaine had more compatibility than most of the schmucks she bedded.

Keith Hernandez

It tells you how much of a catch the Mets first baseman was that Jerry’s first reaction to hearing that Hernandez was bedding his ex-girlfriend was to be jealous of Elaine — though he eventually came around to be jealous of them both. Hernandez is handsome, rich, famous, athletic and marvelously mustachioed, though his need for nicotine ultimately crossed him of the list of Elaine’s potential partners.

Hernandez was such a mensch that he even turned Kramer and Newman from haters into movers.


Who else could possibly compare to Patrick Warburton’s stoic mechanic, New Jersey Devils fanatic and sexually plagiaristic David Puddy? As the most featured on-and-off again boyfriend of Elaine throughout the length of the series (besides the guy with his name in the title, of course), clearly the Seinfeld writers agree with the fan assessment that Puddy is the funniest and most compelling companion that Elaine ever had.

Elaine and Puddy may not have been the best match, given their religious differences, their constant breakups and Puddy’s blasé attitude toward Elaine in general, but he was the best goddamn guy she ever laid — even if “the move” wasn’t his own machination. 

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