Summary

• Larry David's on-screen dating life in Curb Your Enthusiasm became chaotic after his divorce in season 6.
• The show introduces a variety of quirky love interests, from Elizabeth Banks to Sienna Miller, adding comedic depth.
• Larry's awkwardness in navigating relationships is highlighted with hilarious misunderstandings and mishaps with each new romantic partner.

In the quirky universe of HBO's Curb Your Enthusiasm, Larry David's fictional persona was never scripted to navigate the tumultuous waters of romance. Initially tethered to his on-screen marriage mirroring his real-life counterpart, David's character found himself suddenly single after his actual divorce post-season 6. With this narrative twist, the show's dynamic shifted, allowing Larry to embark on a comically calamitous journey through the realm of dating.

After Larry David's character bid adieu to his on-screen marriage with Cheryl, the canvas of Curb Your Enthusiasm broadened to showcase an array of quirky and memorable love interests. From perplexing encounters to hilariously awkward situations, the show paints a vivid portrait of Larry's attempts at navigating the complexities of romance in his uniquely Larry-esque manner. Now that season 12 marks the end of the series, Larry's dating life in Curb Your Enthusiasm has ballooned to include the likes of Elizabeth Banks and even Sienna Miller.

16 Irma Kostroski

Played By Tracey Ullman (8 Episodes, 2021-2024)

In season 11, episode 7 of Curb Your Enthusiasm, Irma Kostroski (Tracey Ullman), bursts onto the scene as a polarizing figure in Larry David's world. Introduced amidst a flurry of political intrigue and comedic mishaps, Irma becomes an unexpected player in Larry's quest to navigate the complexities of civic engagement and personal relationships. Larry's initial interaction with Irma is marked by his pragmatic attempt to befriend her in hopes of leveraging her influence to repeal a burdensome city ordinance.

Their relationship takes an unexpected turn when Irma becomes infatuated with Larry, much to his dismay.

However, their relationship takes an unexpected turn when Irma becomes infatuated with Larry, much to his dismay. Despite finding her repulsive, Larry finds himself entangled in a long-term relationship with Irma, forced to endure her unpleasant company as a consequence of his political maneuvering. While comedy royalty Tracy Ullman's portrayal of Irma is hilarious, the two characters are terrible together, and Larry tells Irma that he has a fake disease so that she'd lose interest in him.

15 Mary Jane Porter

Played By Sherry Stringfield (1 Episode, 2009)

Mary Jane Porter really screwed Larry over. Not only did she not tell him she had a boyfriend while they were dating, but she went and gave that boyfriend Larry’s name and home address the moment he confronted her about the affair. Later, at a restaurant they both happened to be in, the boyfriend identified Larry and chased him out to the dumpsters, where Christian Slater – whom Larry had also irked throughout the episode, unsurprisingly – directed him to Larry’s whereabouts. It can only be assumed that Larry took a beating after the episode cuts to credits.

Mary Jane Porter's betrayal of Larry David transcends the bounds of mere romantic disappointment; it's a saga of deception and repercussions that reverberate throughout the episode. Initially, her failure to disclose her existing relationship while entangled with Larry epitomizes a breach of trust. However, her actions escalate dramatically when confronted by her boyfriend, as she brazenly divulges Larry's personal details without hesitation, making her unforgettable for all the wrong reasons.

14 Gabby McAfee

Played By Julie Bowen (1 Episode, 2021)

In season 11, episode 5 of Curb Your Enthusiasm, Gabby McAfee (Julie Bowen), steps into Larry David's world as a potential romantic interest. Set up on a date by his friend Jeff, Larry's encounter with Gabby unfolds amidst a series of missteps and misunderstandings that epitomize the show's trademark blend of humor and chaos. Their date takes a turbulent turn as Larry navigates a string of social faux pas, from inadvertently offending the sushi chefs with a misplaced greeting to unwittingly exchanging secrets with Gabby.

Their budding connection is tested when it's revealed that Gabby can't keep secrets, as everyone finds out about the secrets that Larry told her. Ultimately, Gabby was never going to be in Larry's life for longer than a couple of dates. Gabby's role in season 11 serves as a reminder of the unpredictable nature of romance in Larry David's world, as he navigates a minefield of social conventions and personal relationships with his trademark blend of awkwardness and charm.

13 Heidi

Played By Rebecca Creskoff (1 Episode, 2011)

Despite Richard Lewis’ warning not to “s**t where you eat,” Larry decides to ask out the hostess at his favorite restaurant. They go on a few dates, but ultimately, the teenage niece she lives with, the smiley faces she puts in her texts, and the $50 she owes Larry that she doesn’t seem to want to pay back all become too much. After breaking up with her, she etches a smiley face into his bald head with sunblock, leaving a sunburnt emoji on his forehead at a funeral, and tampers with his food at the restaurant.

Heidi's tumultuous involvement with Larry extends beyond the realm of romance, infiltrating various aspects of his life with its peculiar brand of chaos. As their relationship unravels, her actions manifest a blend of vengeance and absurdity, leaving a lasting mark on Larry's comedic misfortunes. From her unapologetic manipulation of personal finances to her unconventional methods of retaliation, Heidi's character embodies a unique fusion of eccentricity and unpredictability. However, it is her audacious acts of retribution that etch her name into the annals of Larry's romantic history.

12 Denise Handicapped

Played By Anita Barone (1 Episode, 2009)

Denise Handicapped was so named because that’s what Larry called her in his phone contacts to remember who she was. Frankly, the situations the character found herself in during the season 7 episode were funnier than the character herself. When Larry was disappointed to find that she was in a wheelchair after she was sitting in a coffee shop when they first met, she revealed that she too was disappointed to find that he was bald after seeing him in a cap when they first met. But the character herself didn’t have an awful lot of funny things to say.

Her presence served as a catalyst for some of the season's most memorable comedic setups.

Nevertheless, her presence served as a catalyst for some of the season's most memorable comedic setups. From navigating awkward encounters to confronting societal taboos with Larry's trademark lack of social grace, Denise's character provided fertile ground for comedic exploration. Despite her limited verbal contributions, Denise Handicapped left an indelible mark on Larry's misadventures, reminding viewers of the show's penchant for embracing the absurdities of everyday life with irreverent humor.

11 Jane Cohen

Played By Amy Landecker (1 Episode, 2011)

Jane Cohen's entrance into the tumultuous romantic dynamics of season 8 injected a captivating blend of humor and tension, albeit within a narrative framework that raises eyebrows in contemporary contexts. As a character, Jane exuded a unique charm, brought to life with finesse by Amy Landecker's improvisational prowess and the aloofness she lent to the role. Amidst the chaos of Larry and Rosie O'Donnell's rivalry for her affections, Jane's reactions and interactions provided moments of genuine comedic delight.

One standout instance was her priceless reaction to discovering Larry's clandestine "juicing" escapade, a revelation that unfolds in the hallowed halls of the Baseball Hall of Fame. Landecker's portrayal masterfully captured Jane's blend of incredulity and amusement, further enhancing the episode's comedic impact. Despite the episode's problematic elements, Jane Cohen emerged as a memorable character whose presence added depth and humor to the complex romantic entanglements of Curb Your Enthusiasm's eighth season.

10 Elizabeth Banks

Played By Elizabeth Banks (1 Episode, 2017)

In season 9, episode 3 of Curb Your Enthusiasm, Elizabeth Banks makes a notable appearance, but unfortunately, her dynamic with Larry David's character spells trouble. As Larry finds himself embroiled in a series of misadventures, including a frustrating encounter with a restaurant manager played by Rich Fulcher and a contentious ticketing incident with the police, Banks' character adds another layer of chaos to his life.

Their interaction is marked by a series of mishaps and misunderstandings, as Larry's penchant for trouble seems to rub off on Banks' character. Despite Larry's attempt to seek advice from Salman Rushdie on his fatwa situation, Banks' presence only seems to exacerbate the comedic calamity. As they navigate their respective predicaments, it becomes increasingly evident that they are terrible together, constantly getting each other into trouble with their antics and ill-fated decisions.

9 Lucy Lawless

Played By Lucy Lawless (1 Episode, 2007)

Lucy Lawless, better known as TV’s Xena the Warrior Princess, was the first woman Larry dated after Cheryl left.

Lucy Lawless, better known as TV’s Xena the Warrior Princess, was the first woman Larry dated after Cheryl left. They went to dinner right after Larry injured his crotch and was assigned the nickname “Long Ball Larry” by Leon. The doctor had told Larry not to have sex for a week, so when Lucy invited him back to her place for something to eat (the restaurant wouldn’t serve them as they chose Cheryl in the breakup), he told her so and she said, “I was only talking about dinner, you big a*****e!”

She wasn’t an all-time great Curb Your Enthusiasm guest star, but her appearance was memorable. While Lawless may not have been hailed as one of the show's best, her memorable appearance left a mark on Larry's post-divorce romantic escapades, earning her a place in the pantheon of memorable girlfriends of Larry's in Curb Your Enthusiasm.

8 Rita

Played By Teri Polo (1 Episode, 2020)

In season 10, episode 2 of Curb Your Enthusiasm, Rita (Teri Polo), makes an eventful entrance into Larry David's world. As Larry grapples with a myriad of absurdities, including a sexual harassment complaint from his assistant Alice and a failed attempt to reconcile with Cheryl, Rita offers a glimmer of romantic potential. Their date, orchestrated with Larry's usual penchant for caution amidst his legal woes, takes an unexpected turn as Larry records the encounter as evidence of his innocence.

However, their budding romance is not without its challenges, as Larry's eccentric behavior and preoccupation with his legal troubles threaten to derail their connection. Ultimately, Rita's role in season 10, episode 2 underscores the unpredictable nature of Larry David's universe, as he navigates the precarious balance between romance, friendship, and the ever-present specter of legal scrutiny. Despite their potential as a couple, Larry and Rita's compatibility was questionable at best.

7 Wendy

Played By Amy Pietz (1 Episode, 2009)

In the Season 7 episode "Denise Handicapped," Larry David finds himself entangled in a comedic whirlwind as he juggles two romantic interests, Wendy and Denise. Despite initially pursuing Denise, Larry's bumbling attempts to track her down inadvertently lead him to connect with Wendy, setting the stage for a series of hilariously awkward encounters. While Denise serves as a foil for Larry's comedic misadventures, Wendy emerges as a standout character in her own right, injecting the episode with a dose of humor independent of Larry's antics.

What sets Wendy apart is her ability to hold her own in the comedic fray, delivering lines that land with precision and wit. While Denise may lack memorable quips, Wendy's sharp humor and comedic timing elevate her character beyond the confines of a mere romantic interest. Wendy's ability to stand out in a smaller role underscores the importance of bringing humor and depth to even the most minor parts.

6 Anna

Played By Gina Gershon (2 Episodes, 2004-2007)

Gina Gershon made a couple of appearances as Anna over the years. The most notable of which was in season 4, when Cheryl had allowed Larry to sleep with someone else as an anniversary present, and he almost slept with Anna. They met in a hotel room but were interrupted by an earthquake. Anna has always been very blunt with Larry, and what sets her apart as a character is her refusal to tiptoe around Larry's idiosyncrasies, instead opting to confront them head-on with unapologetic sarcasm.

Gershon's portrayal infuses Anna with a sharp wit and a no-nonsense attitude that perfectly complements Larry's buffoonery, resulting in comedic exchanges that are as hilarious as they are cringe-worthy. As one of the show's standout characters, Anna exemplifies the comedic gold that arises from the collision of Larry's quirks with characters who are unafraid to challenge his antics.

5 Donna

Played By Megyn Price (1 Episode, 2020)

In season 10, episode 4 of Curb Your Enthusiasm, Donna (Megyn Price), enters Larry David's chaotic world with a mix of intrigue and uncertainty. As Larry grapples with a series of mishaps and misunderstandings during a destination wedding in Cabo San Lucas, Donna becomes a focal point of potential romantic entanglement. Their budding relationship takes an unexpected turn when Larry discovers an older photo of Donna, prompting concerns about her yo-yo dieting habits. Despite his reservations, Larry extends an invitation for Donna to join him at the wedding.

Despite the challenges they face, Larry and Donna's interactions provide moments of levity amidst the chaos, offering glimpses into the unpredictable dynamics of romance in Larry David's world. Ultimately, Donna's role in Curb Your Enthusiasm serves as a reminder of the absurdities and unpredictabilities of the series. While Larry and Donna seemed great together and had a rapport unlike most of his other relationships, his obsession with her dieting habits and sleeping with Cheryl during the vacation kept them from becoming more serious.

4 Sienna Miller

Played By Sienna Miller (3 Episodes, 2024)

Sienna Miller is a Curb Your Enthusiasm season 12 guest star as a captivating new character who ignites sparks with Larry David. Introduced as a romantic interest for Larry, Sienna's presence adds an intriguing dynamic to the season as their flirtation unfolds amidst the chaos of Larry's universe. Their interactions are marked by witty banter and undeniable chemistry, as Larry navigates the complexities of romance with his trademark blend of charm and awkwardness. Their first date proves promising, as Larry even helps improve her acting.

However, as season 12 hasn't yet concluded, it isn't clear how their relationship will evolve. While their connection appears to be blossoming, the unpredictable nature of Larry's world leaves viewers on edge, wondering whether their romance will endure or meet a typical Larry David-esque demise. Nevertheless, she's potentially one of the best of Larry's girlfriends in Curb Your Enthusiasm.

3 Loretta Black

Played By Vivica A. Fox (11 Episodes, 2007-2009)

Leon’s sister wasn’t initially a love interest for Larry. She moved into the house with her family while Larry was still married to Cheryl. But after Cheryl moved out, they got together and spent a few episodes in a relationship. At the start of season 7, Loretta was diagnosed with cancer before Larry could break up with her, so Larry tried to get Loretta to break up with him. However, before Loretta was diagnosed with cancer, she and Larry's relationship was going great.

One standout moment was when she fought Larry's battles with Susie for him, leaving Susie stunned and speechless for the first time ever. Fox's performance captured the nuances of Loretta's character with finesse, balancing moments of vulnerability with her trademark sass and wit. The portrayal brought Loretta to life with authenticity and charisma, leaving a lasting impression on Curb Your Enthusiasm fans.

2 Shara

Played By Anne Bedian (2 Episodes, 2011-2017)

Many fans consider season 8’s “Palestinian Chicken” one of Curb Your Enthusiasm’s best episodes. Larry finds himself torn between his Jewish faith and the amazing chicken served at a new Palestinian place in Los Angeles. He begins a love affair with Shara, who works at the restaurant, after she's impressed by Larry’s attempts to remove Marty Funkhouser’s yarmulke in the parking lot. She was so great that it made Larry question his allegiance to Judaism.

Shara would later reappear in season 9, equally impressed by the fatwa Larry had managed to get slapped on him. Her continued presence served as a reminder of the complexities of loyalty in Larry's comedic universe. Shara's character not only contributed to the comedic brilliance of "Palestinian Chicken" but also left an enduring legacy that resonated throughout the series, making her a memorable addition to Larry's girlfriends in Curb Your Enthusiasm.

1 Cheryl David

Played By Cheryl Hines (107 Episodes, 2000-2024)

No one has topped Cheryl as a romantic match for Larry. Fans can understand why she left him, since it isn’t easy living with Larry David, but for the time they were together, they had impeccable chemistry and shared a lot of funny scenes. The real David has said that he knew Cheryl Hines was right for the part of his wife almost immediately during the audition because she played perfectly against anything he said. Hines did a brilliant job of playing the long-suffering wife, reacting hysterically to the situations Larry finds himself in.

Cheryl Hines' portrayal of Larry David's long-suffering wife, Cheryl, in Curb Your Enthusiasm remains a quintessential aspect of the show's success. Hines brought a perfect balance of exasperation and affection to her character, creating a dynamic on-screen chemistry with Larry David that was both believable and comedic gold. Their interactions were marked by a natural rapport that lent authenticity to their on-screen marriage, making their scenes together a joy to watch.