Larry David’s fictional self on his HBO sitcom Curb Your Enthusiasm was never meant to have any love interests. At the beginning of the series, he was married, just like David was in real life. However, he’d always pledged that if he wasn’t married in real life, he wouldn’t stay married on the show.
When his real-life wife left him after Season 5, David wrote a Season 6 arc in which Cheryl would leave his character, freeing him up to get back on the dating scene. So, Curb Your Enthusiasm fans, let's rank the love interests the show gave Larry.
10 Mary Jane Porter
Mary Jane Porter really screwed Larry over. Not only did she not tell him she had a boyfriend while they were dating, 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 – who Larry had also irked throughout the episode, unsurprisingly – directed him to Larry’s whereabouts. Then we cut to the credits, but we can assume Larry took a beating. Mary Jane Porter was the worst.
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 him back all become too much.
He decides to break up with her. So, 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. There were some funny ideas in her arc, but she wasn’t too memorable.
8 Denise Handicapped
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 that was titled after her were funnier than the character herself.
For example, 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.
7 Jane Cohen
Jane Cohen is the bisexual woman who dates both Larry and Rosie O’Donnell in season 8, leading to an intense rivalry between the two comedians to see who will be the one to win her heart.
Although the episode as a whole is quite problematic, making comments about sexuality that just don't fly in 2019, Jane as a character was a lot of fun. Amy Landecker did a great job with the improvisation and the aloofness of her character. Her reaction to finding out that Larry had been “juicing” – at the Baseball Hall of Fame of all places – was priceless.
6 Lucy Lawless
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 guest star, but her appearance was memorable.
Larry dated two women in the Season 7 episode “Denise Handicapped,” as he lost the phone number of one and ended up hitting it off with the other while he was trying to track her down. Wendy was arguably the funnier of the two, since Denise didn’t really have many funny lines in comparison.
Denise was more of a foil for Larry, but Wendy was funny on her own. When it comes to smaller parts in sitcoms, that's an important trait.
Gina Gershon has made a couple of appearances as Anna over the years. The most notable one 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, which is always going to be hilarious. The funniest characters in the show are the ones who refuse to enable Larry’s buffoonery, and Gershon has always done a terrific job of playing against Larry’s social ineptness with an aggressively sarcastic edge.
3 Loretta Black
Leon’s sister wasn’t initially a love interest for Larry. In fact, 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 he spent a few episodes trying to get out of it, which was a little uncomfortable. Still, Vivica A. Fox played the character wonderfully, with the pinnacle of her arc being the dream sequence in which she screams Susie out of the house.
Many fans consider Season 8’s “Palestinian Chicken” to be one of Curb Your Enthusiasm’s all-time greatest episodes. In it, Larry finds himself torn between his Jewish faith and the amazing chicken served at a new Palestinian place in Los Angeles. He ends up starting a love affair with Shara, who works at the restaurant, after she was 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.
1 Cheryl David
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 situations like...well, the ones that Larry constantly finds himself in.