TV Database Seinfeld (1989)

At 35, I'm not married. Hell, I haven't even been laid. Not exactly a badge of honor or some incel anthem—just a quiet comfort in the lifestyle I’ve built. Relationships? Sure, they come with companionship, shared joy, someone to split the Uber bill. But people are messy, and I’ve got the social adaptability of a broken vending machine. Also, my teeth are kind of a horror story. Let’s not talk about that.

So when The Engagement kicks off season seven of Seinfeld with Jerry and George pondering whether it’s time to grow up—dreaming about companionship and the meaning of caring for someone—you can see the show gently poking at that societal script. The kind that suggests we’re all supposed to be looking for someone, settling down, building a life. And I get it. I’m not anti-relationship by any means; I can see the appeal of having someone who truly values your worth as a person and invites you to do so in return. But if you’re someone like me—or like Jerry—who’s built a lifestyle around habits, solitude, and a certain emotional detachment, then the idea of upending all that for the unknown (even if I do somehow get lucky enough to meet someone) can feel more like social obligation than personal desire.

And that's the tension this episode toys with in the typically Seinfeldian comedic ways. Jerry's hang-ups get the best of him again, while George stumbles blindly into “adulthood” because... well, because he’s George. And the results are predictably disastrous.

On Jerry’s side, it’s a typical sitcom gag that only works if you completely ignore the existence of something we humans called talking about it. His issue with his girlfriend is something that could’ve been solved with a simple “hey, this thing you do kinda bugs me,” but of course, Jerry would rather eject himself from mild discomfort than risk a real conversation. Which, honestly, tracks for someone that neurotic. He’d rather preserve his perfectly controlled lifestyle than deal with the chaos of connection—and that’s part of what makes him both relatable and hilariously pathetic.

George, on the other hand, overcorrects so hard he veers off a cliff. Watching him spiral from proposal euphoria to regretful couch blob within 48 hours is both sad and exactly what you’d expect. You can tell the writers remembered this is a show with “no hugging, no learning” and just went full tilt into the tragic clown of it all in this season premiere. After a brief flirtation with growth back in season 5, he’s now cartoonishly regressed to his original Constanza mannerisms—dropping misogynistic chess metaphors, fumbling through impulsive decisions, and walking straight into a relationship he’s clearly unfit for. Watching him try to act like a grown-up while visibly squirming in his own skin? Pure karmic punishment gold.

I guess that it is meant to be funny that someone like me with limited social finesse could think of several ways to mediate some of these situations the sitcom characters constantly run into. You want to watch different shows? Split the nights, alternate picks, do anything but let it rot into resentment. But I suppose that's where the appeal of these characters lies—they’re not supposed to be wise. They’re emotionally stunted, chronically self-sabotaging, and comfortable in their dysfunction, which provides that comfort for being just a little smarter for recognizing the easy fix they’ll never even consider. But it is still a little annoying because, once again, a little communication goes a long way in breaking TV drama and comedy cliches.

Of course, that's where the episode falls a little flat in terms of challenging the characters' perspectives, because both Jerry and especially George's situation reinforces Kramer's incel-flavored views that marriage is a prison. But to be fair, he’s less a woman-hater and more of a libertine Luddite—he doesn’t want to be tied down to anyone or anything. Richards plays that commitment-phobic chaos with such bizarre enthusiasm that it swerves into a kind of free spirit philosophy. He’s not angry at women—he’s just allergic to structure and these social obligations we keep boxing ourselves in.

Meanwhile, there’s a B-plot involving Elaine, a sleepless night, and an extremely American problem: a neighbor’s yappy dog. I’m from Singapore, where barking laws are real and enforced, so this subplot just read like an anxiety dream set in Brooklyn. That said, Newman’s disgust for dogs and Kramer’s wildly irresponsible solution make for a few funny moments, especially if you’re a fellow cat person who’s been ambushed by one too many tiny bark machines during my part-time job distributing leaflets.

In the end, “The Engagement” isn’t one of the series’ top-tier episodes, but it sets the tone for a season that might actually pretend to challenge its characters—until, inevitably, it doesn’t. I don't mind having the comfort food of familiarity, but man, it was kinda nice having the illusion of subversion and clever plotting for a moment. Ah well.

Following the gendered neurosis of “The Engagement,” The Postponement tries to shift perspectives, dragging Elaine into the emotional splash zone for once. But while it technically balances the screen time, it doesn't quite balance the substance. Instead of exploring Elaine’s own relationship dysfunction in the same way George and Jerry get theirs aired like laundry in a hurricane, the episode mostly turns her into collateral damage for a gag about gossip.

The premise—Elaine confiding in a rabbi who turns out to be the nosiest mouthpiece in the building—is funny in that classic Seinfeld "watch a situation spiral until someone cries" way, but it leans more on setup than character. Elaine’s not doing much; she’s being done to. And for a show that built its reputation on dissecting the petty flaws and fragile egos of its leads, that’s a missed opportunity. We know Elaine is capable of wild self-sabotage. Why not give her a stage to trip on her own shoelaces like the guys do?

Meanwhile, Susan Ross (Heidi Swedberg) continues her strange run as sitcom fiancée-shaped furniture. She gets to speak, sure, but her main role is to act as an immovable wall for George to bounce his insecurities off of. She’s not mean, not exactly, but she exists solely to challenge George's cowardice—and by extension, provide the setup for yet another unflattering Costanza maneuver. It's funny. It works. But it also pushes her toward that dreaded “shrew” zone, where female characters in comedies go to die when no one bothers writing them with interiority.

That said, George's whole arc here works brilliantly in terms of comedy. I couldn't imagine being married to someone who probably dislikes you as much as you loathe her. Clearly, "opposites attract" is a myth, because as Jason Alexander would later observe, he and Heidi lack the kind of chemistry to make their relationship believable. This isn’t the slow rot of a long-term marriage; they’ve been engaged for what, an episode? And it’s already dead on arrival. And look, I’m not anti-relationship, but watching disasters like this really does make me grateful I’m not dealing with the hassle of being with people. It’s all just so much work.

Also—minor side note, but kind of a hilarious one—George’s pick for his postponed wedding date, the so-called “Spring of Rebirth”? Yeah, that’s literally my birthday. March 21st. Fitting, considering my free agent lifestyle and this man's attempt to delay his doom with the emotional equivalent of a Hallmark slogan.

But instead of dealing with his relationship mess maturely, George of course picks up all the wrong lessons from an insensitive jerk at Monk's, and then further learns yet another morally confused lesson during his second attempt (this episode) to break off with Susan. For a show that’s famously against its characters learning anything, it often makes for great comedy watching them take away the worst possible interpretation of a situation and dig their own graves with it.

Not Kramer though, as he is doing whatever the hell he wants in his own plot dimension—this time revolving around caffeine, betrayal, and karmic exemption. The man preaches loyalty like a mobster, then folds the moment the rules threaten his own comfort. It’s vintage Kramer: moral elasticity meets physical comedy, plus a side of delusion. You can’t argue with the formula—mainly because he won’t be around long enough to hear it.

Overall, The Postponement remains another decent one, but doesn’t quite reach Seinfeld’s upper tier, not even close. Perhaps the peak is long gone by this seventh season. Ah well.

This was an alright episode — not top-tier Seinfeld chaos, but a steady stream of good laughs and a few truly great character moments that kept it afloat.

Kramer's free-spirited nature somehow manages to sabotage him in the most Kramer way possible: favoring immediate gratification over long-term gains. Only Kramer could turn a slam-dunk lawsuit into a case study in how to trip over your own shoelaces — and somehow walk away thrilled about it. His ability to bulldoze through a legal negotiation like he’s ordering at a drive-thru is peak Kramer: favor the trivial, ignore the obvious, and then act baffled when it all goes sideways.

Meanwhile, George’s subplot is the kind of low-stakes, everyman frustration that hits a little too close to home. Watching him crusade for the dignity of a man who has to stand all day (because, honestly, standing jobs are a special kind of hell) is almost relatable — until, of course, George’s signature cosmic punishment kicks in. As Seinfeld law dictates: no good Costanza deed goes unpunished.

Even Jerry, who usually floats above the nonsense with his smug detachment, gets knocked down a peg this time. His obsessive need to be right — to the point of chasing down obscure Tuscan real estate out of pure spite — backfires in one of the few times he actually stumbles into George-level embarrassment. It’s a rare, satisfying sight: Jerry getting hoisted by his own pettiness.

Also worth shouting out is the arrival of Phil Morris as Jackie Chiles, a glorious parody of Johnnie Cochran that absolutely nails the moment it aired (October 5th, 1995, two days after the O.J. trial mania ended). Even if you don't catch the Cochran reference, Morris’ rapid-fire outrage and bulletproof confidence are hilarious on their own. It's the kind of bit that's deeply rooted in its time but still funny decades later — thanks to a delivery so righteous you almost believe Kramer has a real case.

Then there’s Bob Cobb — a.k.a. The Maestro — who is just an Olympic-level pompous jerk. Mark Metcalf (yes, The Master from Buffy) brings an amazing sliminess to the role, making you both laugh at and despise him every time he insists people call him Maestro like he’s conducting the New York Philharmonic instead of, you know, local benefit concerts.
And I'll admit: when Gmail asked me to create a name for one of my first accounts, I also thought "Maestro" sounded cool as hell (I spelled it as "Meister" lmao). So I kind of get the appeal. But still — the idea that Elaine, queen of picky dating standards, puts up with this guy feels like a cosmic joke in itself.

The episode’s structure is a little more loosey-goosey than usual — it feels less like a masterplan and more like a handful of solid B-plots tossed into a blender. But that’s part of its charm, too, particularly when the characters themselves are so reliably funny. It’s a middle-of-the-road Seinfeld, but in that "even their 7/10s are better than most shows’ 10/10s" kind of way.