George Costanza is Jerry Seinfeld‘s best friend, but he’s a lot more than that — he’s neurotic, miserly, self-centered, tormented, delusional, untrustworthy, pitiful, irresponsible, the list continues endlessly. On rare occasions, one might see his good side, which actually cares about people and their problems (usually involving children), but for the most part, he’s just the worst.

Although it remains a constant surprise that George finds romantic partners and even gets engaged to living, breathing women, it’s not really remarkable that he finds it impossible to retain them. Below are some of the finest episodes of Seinfeld, each of them involving a George Costanza “situation” that is hilarious and pathetic at the same time.

10 The Wink (S7 E4) — 8.6

George gets a little grapefruit in his eye; it gets mostly washed out, but he continues to wink in response to the acidity while being completely unaware of the fact. This causes a chain reaction at the NY Yankees, where George’s winking insinuates to his boss, Mr. Wilhelm, that one of his colleagues, Morgan, might be up to no good.

At the same time, Kramer sells a birthday card meant for Mr. Steinbrenner (again misinterpreting the ocular movement), which leads to Morgan getting fired because he never got to sign the card like he was supposed to. George is left stuck with a worse job: more hours, and not much of a raise.

9 The Hot Tub (S7 E5) — 8.6

The Yankees request George to take a group representing the Astros out for a “good time,” after which he begins to mimic their Texan drawl and crude terms of endearment. This behavior rubs off on a visiting athlete, Jean-Paul, who gets kicked out of Elaine’s apartment for insulting her neighbor (and her baby.)

Kramer’s latest dip in the cesspool that his is mind leads him to buy a massive hot tub all for himself. The resultant power shortage almost loses Jean-Paul his attempt at redemption, but the hot tub returns later when George is forced to take a long hot soak with Mr. Steinbrenner to get rid of his “stress.”

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8 The Summer Of George (S8 E22) — 8.6

After receiving a “severance package” from his job, Costanza realizes that he can live guilt-free for the next three months, leading to the famed Summer of George. In true form, he does nothing: spending most of his time lounging around his home in sleepwear and claiming to be too exhausted to make his usual trip to Jerry’s place.

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Later, George has an accident by slipping on a dropped invitation, a callback to the time he accidentally “murdered” his fiancée, resulting in months of physiotherapy and training before he can return to normal.

7 The Tape (S3 E8) — 8.7

When Elaine decides to prank Jerry by leaving a fake-sexy voice note on his tape recorder, the other three fantasize about it, completely clueless as to the identity of the mystery woman. George is the first to find out, which is when he begins to “have feelings” for her (clearly based on pure lust.)

It gets a lot more awkward because this is the episode in which he tries to regrow his hair with help of some strange Chinese remedy. At the end, Elaine makes her exit from Jerry’s apartment while the boys fight over the right to listen to the tape.

6 The Package (S8 E5) — 8.8

One of the best episodes in the series, “The Package” simultaneously shows George at his best and his most pathetic — he foolishly allows Kramer to click “sexy” pics of him to send to a random woman whom he believes is interested in him.

After getting the film developed, however, it is Newman who finds George’s embarrassing poses and denounces him for being part of a “mail-order pornography ring,” but this is because he also finds an unknown man’s almost-nudes in the same collection. It turns out to be Ron, who added his own photographs as he suspects that George was trying to hit on him, albeit indirectly.

5 The Invitations (S7 E24) — 8.8

George is almost certain at this point that marrying Susan would destroy him in every possible way, so he tries to sabotage the wedding as much as he can. He tries to scare her off by pretending to be a smoker, which only confuses her, and demanding that she sign a prenup, which she agrees to do (after laughing at him for his delusions.)

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The only thing that actually works, however, is his peculiar penny-pinching — ordering the lowest quality wedding envelopes in order to save money, leading to Susan getting poisoned to death by the inferior adhesive used.

4 The Rye (S7 E11) — 8.9

The Rosses invite the Costanzas over for dinner, to which the latter bring along a loaf of marble rye bread from Schnitzer’s. Being snooty, they “forget” to put it out for dinner, so Frank steals it back out of spite.

George spends most of this episode plotting how to save face, finally reaching the conclusion that the only way would be to “replace” the bread by bringing another piece and leaving it somewhere in the Ross household. Unfortunately for him, Kramer’s flatulent horse (from being fed literal beef) brings Susan’s parents home before George can complete his scheme. He subsequently gets caught red-handed trying to “fish” the marble rye that Jerry steals from a poor old woman.

3 The Nap (S8 E18) — 8.9

It’s quite unbelievable that George only learns the under-desk nap trick in the eighth season, but the storyline plays out as hilariously as one could hope for. To make the process comfortable, he asks a contractor to help him modify his secret nook, such as installing an alarm clock, as well as sections for an assortment of snacks.

However, when Mr. Steinbrenner comes to George’s office for some obscure musical reason, he hangs around for him to “get back.” To avoid being exposed, Costanza begs Seinfeld to fake a “bomb threat” to the Yankees, but this only results in his boss finding him snugly located below his desk. George gets away with it at the end, though, but his happy place is completely destroyed by Steinbrenner’s mania.

2 The Marine Biologist (S5 E14) — 9.2

“The Marine Biologist” is one of George Costanza’s best performances in Seinfeld; he almost succeeds in living his best life — having a respectable profession, obtaining a woman’s attention because of said profession, and performing the supremely praiseworthy act of rescuing a beached whale.

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Unfortunately, the Costanza curse plays its hand once again, and when Diane discovers that he had faked the whole thing, she tells him to “go to hell!” and walks away.

1 The Opposite (S5 E21) — 9.6

George tests out his latest theory (that going against his intuition is his best chance for success) and it provides some astonishing results. Not only does he get a date with an amazing woman, but he also finds himself a dream job working for the New York Yankees by blatantly accusing Mr. Steinbrenner of making poor team management choices.

Interestingly, “The Opposite” is as much an Elaine episode, because where George prospers, she seems to experience abject failure: losing her job because of her addiction to Jujyfruits, consequently “becoming George” by the end.

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