As filming wraps on the ninth season of Curb Your Enthusiasm (six years after the eighth season aired), we officially can’t wait to be part of Larry David’s cringey wonderland again. With that in mind, we thought it might be fun to re-live some of the show’s most toe-curlingly awkward moments - something Curb was never short of in its 11-year run. Larry David’s semi-improvised, semi-autobiographical comedy show definitely deserves a place in TV history as one of the most painfully awkward sitcoms ever created, in the best way.

In 2000, the Seinfeld creator moved on from the straight-laced format of a sitcom filmed in front of a studio audience to the kind of comedy show that feels a little too real for comfort. Curb Your Enthusiasm is, at times, the kind of show you watch through your fingers because the cringe factor is so real. Whether these embarrassing situations are Larry’s own fault or not, though, you can’t help but feel sorry for him, because Curb is essentially about how strange and bewildering everyday life can be.

It never stays too real, however, since Larry David’s social graces are pretty much non-existent. Larry’s willingness to come out and say precisely what he thinks about someone or some wrong doing towards him is something we all secretly wish we could do - just maybe not to the same insane degree. In anticipation of another tidal wave of Larry David awkwardness in season 9, take a look back at some of Curb’s most squirm-worthy moments. Ready, set, cringe!

The Dinner Party With The Holocaust Survivor

Those familiar with Larry David’s brand of comedy will know that he doesn’t shy away from controversial subjects, but thankfully, the serious nature of something like the Holocaust is never something he is directly joking about. Take, for instance, the incredibly cringe-inducing episode "The Survivor" in which Larry invites a man who survived Auschwitz to dinner. Meaning well, Larry also invites someone he believes is another Holocaust survivor in the hope they can bond, when in actual fact, he has invited someone from the reality TV show, Survivor. (You can probably guess where this is headed!)

The dinner party reaches peak cringe when the reality star from Survivor begins telling Larry’s dinner guests about his time on the show. He complains about the poor food, the hot temperatures, and having to wear flip-flops instead of sneakers. Cue a very angry and hurt Holocaust survivor telling the vain reality star what true human survival means. Ouch.

When Larry Is Mistaken For A Pedophile

This is probably the best example of Curb’s roller coaster of awkwardness at its finest. It all starts when Larry is asked by a manipulative little girl if he would give one of her dolls a haircut. Larry complies and before you know it, the girl cries to her mom to complain about what Larry did. To square things with her mom, he promises to replace the doll’s head with the original, longer haired doll.

This is where things go from "woah" to "WTF" when Larry finds a replacement doll’s head at his friend Jeff’s house and hides it from Jeff’s wife by shoving the doll head down his pants. The fibers in the doll’s hair itch and he ends up telling a doctor exactly why a rash has developed down there. But the most toe-curling moment of all is when Larry runs into the little girl again at the movie theater and gives her a hug. Unfortunately for Larry, he was hiding a bottle of water from the theater usher in his pants and the girl runs away shouting “Mommy, the bald man’s in the bathroom and there’s something hard in his pants!”

The Unfortunate Typo In The Obituary

In the episode entitled "Beloved Aunt," Larry is asked by his wife’s family if he could write an obituary in the newspaper for a recently deceased relative of theirs. Being a writer, Larry feels honoured to be asked and proceeds to write her obituary. Unfortunately for Larry, the newspaper prints out the obituary with a glaring and pretty offensive typo, managing to replace the A in aunt, with a C. I'm sure you can figure that one out.

Awkwardly, Larry is the last one to know about the error and drops by his wife’s parents home to find his mother-in-law distraught with fresh grief about the typo and the entire family pointing the finger of blame on Larry. Despite Larry’s protest of innocence that it was a mistake on the newspaper’s part and not his, his extended family don’t want to hear it and he is soon kicked out of the house. His father-in-law tells him he was thankful that Larry was not also in charge of the headstone!

Hires His Friend’s Girlfriend (And Grows To Hate Her)

It’s generally a good rule of thumb never to do something like this in real life, unless you happen to know and like the person a lot, which wasn’t at all true in Larry’s case - hence why things got pretty awkward, fast. In one episode from the show’s sixth season, Larry hires his friend’s new girlfriend as an assistant in his office. Larry being Larry, this gets old pretty quickly and he finds himself in hot water with his friend over the issue.

Larry’s trivial complaint is that his friend’s girlfriend, Cha-Cha, always insists on speaking to him when he leaves the bathroom. Cha-Cha meanwhile happens to let slip to her boyfriend that Larry visits the bathroom an unhealthy amount of times during the day. Larry and his friend Richard end up arguing about the whole thing until they begin one-upping each other about who has the most beautiful colon. No, really.

The Nazi Pillow Sham

Usually, the awkward situations Larry finds himself in are largely caused by his own lack of grace or compassion towards someone, but in this instance, Larry tries to do the nice thing and it still blows up in his face. When Larry begins dating a woman with a flamboyant kid, he discovers the boy has a passion for fashion and the show Project Runway. As the young boy’s birthday approaches, Larry wants to get him something he knows he’ll love - a sewing machine.

The boy adores his present from Larry, but his mom, on the other hand, is less than impressed (which says more about her than Larry). Things go from bad to worse when the boy reveals a pillow sham he made using the sewing machine. Since the boy previously walked in on Larry drawing a swastika on a magazine page for a joke, he loved the design of it and embroidered this onto a pillow sham. Naturally, Larry is accused by the adults of teaching the boy to make this monstrosity and there’s no way for him to dig himself out of that hole.

Believing Someone Would Use Parkinson’s Disease As An Excuse To Annoy

In case you hadn’t realized already, Larry David is not the type to hold back when he feels someone is encroaching upon his life (even in the tiniest way). But of all the trivial stuff he has complained about to people throughout the show, his run-in with Michael J. Fox has to be the pettiest of all. Appearing as himself on the show, the good-humoured star of Back to the Future plays Larry’s upstairs neighbour in New York.

One night, Larry hears Fox clomping about in heavy boots above his apartment and has it out with him. MJF apologizes and explains that he has to wear sturdy boots because of his Parkinson’s disease. In another incident, Fox hands Larry a fizzy drink and when Larry opens the bottle, it explodes on him – something MJF also blames on his Parkinson’s disease. This leads Larry to believe that Fox is using his disease as an excuse to be a jerk. Unsurprisingly, Larry's views land him in hot water with pretty much everyone!

Helped A Girl On Her First Period

The first time a girl experiences her period can be embarrassing and alarming enough without the presence of a middle-aged man. Throw Larry David into the mix and this is one rite of passage a girl isn’t likely to forget in a hurry. This is what happened to a poor girl scout selling cookies door to door when she reaches Larry’s house and mother nature chooses this of all places for her to start menstruating.

In his own weird way, Larry does his best to accommodate the girl by fetching “some stuff” his ex-wife left behind. When he returns with a box of tampons, he hands them over to the girl who goes to the bathroom and has no idea what to do. Fortunately, she has Larry David to read the instructions through the bathroom door to her and Larry is so pleased with himself for understanding how it all works that it makes for one of the most hilarious and wonderfully cringey moments in the whole show.

The N-Word Mixup

The blueprint for Curb (and most comedies in general) is one thing spiralling out of control, causing a domino effect of bad situations. This is Larry David’s life in a nutshell and this was never more apparent and painfully awkward than when Larry is overheard using the N-word by a black man. The worst part is, Larry was simply quoting a racist guy he had overheard in the men’s bathroom in a conversation with his girlfriend - but by then, it’s too late for explanations and Larry digs himself deeper and deeper.

Repeating a racial slur he heard in a men’s toilet cubicle not only leads a black man to call him a “despicable, bald son-of-a-b*tch,” Larry’s faux pas also has consequences for his best friend, Jeff. In this same episode, Jeff is due to have an operation and the man Larry inadvertently insults just so happens to be Jeff’s surgeon. Getting his own back on Larry, the surgeon shaves Jeff’s head as a warning to anyone who associates with such a racist a-hole. Oops.

Larry’s Unfortunate Trouser Material

Starting as it meant to go on, Curb Your Enthusiasm got off to a very awkward launch in the first ever episode, which involved Larry David’s trousers. Unfortunately for Larry, the stiff material his trousers are made out of kinda makes it look as if he is a little more excited than he actually is. This is embarrassing enough for Larry when he notices the blunder at home, but things soon get a whole lot more awkward when he and his wife Cheryl leave the house.

When he and Cheryl go to see a movie, Larry’s "pants tent" (as the episode is titled) get him into a very cringey situation and into considerable hot water with his wife and her friend. While sitting next to Larry in the movie theater, Cheryl’s friend Nancy notices Larry’s apparent arousal and believes he’s attracted to her. Larry tries to explain but both women are unconvinced and pretty pissed about the whole thing. Poor Larry.

The Misogynistic Poker Game

What starts out as a fun, high-spirited poker game with a bunch of friends quickly turns sour because of Larry’s poor choice of words towards one player. Caught up in the excitement of the game, Larry asks one player what his cards were and is so surprised at how good they were, he winds up calling him a c*nt for not playing with such high cards. The pin-drop silence that follows is the ultimate in awkward tumbleweed moments as everyone tries to make sense of what they just heard.

One by one, the other poker players decide to call it a night and Larry is quickly labelled a misogynist in the days that follow. (It doesn’t help that in the same episode, an eyewitness mistakenly believes that Larry is beating his wife). When his wife, Cheryl, points out how inappropriate Larry’s outburst was, Larry isn’t apologetic, only admitting that in hindsight, he should’ve used the word "pussy" instead.

Larry Joins An Incest Survivor’s Group

Yes, this is every bit as awkward and messed up as it sounds, but, as usual, in Larry’s case, it isn’t all it seems. Larry gets himself into this mess after agreeing to accompany an old girlfriend to an incest survivor’s group. In the group, everyone takes their turn to tell other members in the circle about their experience with incest. Once it is Larry’s turn to share, he supportively fabricates a story of his own, abruptly disclosing to the rest of the group that he had sex with his uncle when he was 12.

Feeling the need to elaborate further, Larry ends up saying that his uncle was an osteopath. Unfortunately for Larry, he bumps into his (entirely innocent) uncle a few weeks later and is forced to introduce him to the head of the incest survivor’s group. Upon realizing this is the same man who supposedly violated Larry as a boy, the group leader loses her shit and practically drags Larry’s poor bewildered uncle out of the room. Life lesson from Larry David: Never lie (especially not about incest).

Larry Offends Two Paraplegic Women

Of all the despicable and selfish things Larry has done, this is pretty high on the list. Larry asks a woman out on a date, not realizing that she is in a wheelchair. In typical Larry David fashion, he lets her know that he finds it a little off-putting but gives the relationship a shot (particularity since she gets him invited to parties he wouldn’t otherwise have access to). After a while, Larry loses her phone number and can’t find her, since he never knew her full name - having entered her contact name as "Denise Handicapped."

While out looking for Denise, Larry runs into Wendy - another paraplegic woman - and asks her out on a date. (Larry also assumes the women may know each other, based solely on the fact they are both in wheelchairs!). The real cringey cherry on top is when he spots Denise on his date with Wendy. Not wanting Denise to see him with another woman, Larry conveniently wheels Wendy into a closet. A true gentleman.

Steals Flowers From A Roadside Memorial

Pinching flowers from a memorial site is pretty despicable as it is, but as usual, Larry’s crime is far worse than it appears. The flowers Larry steals are actually from the memorial site of his close friend’s mother. Because of a trivial feud Larry and his friend, Marty Funkhouser, had over a $50 bill, Larry sees taking some roadside flowers as equal payback. Hoping to win favour with a school administrator, Larry helps himself to three bouquets from the memorial, figuring they won’t be missed.

The feud that led Larry to literally rob flowers from the grave came out of being improperly paid back. Marty owed Larry $50 and paid this back to him, but Larry had some complaints about the condition of the bill he received (yep, LD really is this petty). Larry bemoaned the fact that the $50 bill had been kept in Marty’s sweaty gym sock and while this is gross, it’s still the money owed to him. Larry is found out in the end and it costs him a lot more than $50...

Larry Is Caught Wearing Woman’s Panties

Larry’s manager and closest friend, Jeff Greene, is usually the one helping Larry get out of a pickle, so when Jeff lands himself in extra-marital trouble, it’s time for Larry to step up and be a good friend. When Jeff’s wife, Susie, finds a pair of woman’s panties in the glove compartment of his car, she demands an explanation and the only excuse Jeff can come up with at the time is that they belong to Larry.

Larry reluctantly agrees to his embarrassing new panty-wearing fetish if it means saving his best bud’s marriage. Unfortunately, Larry’s bizarre "secret" doesn’t stay a secret for long when he is asked - in another thread to the episode - to return a pair of trousers that weren’t paid for. Larry removes his pants to reveal the hot pink panties beneath, in front of an officer and a shocked Susie who finally believes Jeff’s lie.

Larry Gives Susie a "Ride"

via youtube.com

Fans of Curb will know that Larry and Susie (the irritating and tempestuous wife of his best friend, Jeff Greene) never exactly saw eye to eye. A running gag throughout the show was Susie’s knee-jerk hostility towards Larry at the slightest provocation. The fact they can’t stand each other is what makes this excruciatingly cringey scene all the more hilarious. In one quick car journey, Larry gets to know Susie far more than he ever bargained for.

The previous week, Larry drives his girlfriend home in a car with a broken passenger seat that violently shakes and vibrates - giving her an orgasm in the process. So when Susie tells Larry she needs an emergency ride, this horrible thought dawns on him and he drives as slowly as possible. It isn’t long before Susie gets some joy from the seat and she starts moaning, while Larry starts wailing in horror and disgust. Watching Larry writhe and cringe at the sound of Susie is so awkward, yet so hilarious!

Sources: uproxx.com, hollywoodreporter.com, theglobeandmail.com