While the specific timeline of their early relationship is largely unknown, rumours surrounding a potential romance between Jesse and Billie first began to surface on October 13, 2022, after the pair were captured by TMZ out for dinner in West Hollywood.
Less than one week later on October 18, the rumours appeared to be confirmed as the couple were photographed kissing outside a restaurant in Studio City, Los Angeles.
Billie and Jesse further confirmed the rumours of their relationship during their Halloween celebrations, with the new couple dressing as a baby and an old man.
Although the new couple seemingly poked fun at criticism surrounding their 11-year age gap, fans were not impressed with the look, with many taking to Billie's Instagram comments to condemn the "extremely disturbing" look.
“Billie Eilish and Jesse Rutherford’s matching Halloween costumes are incredibly sick and twisted - especially with their age difference and power imbalance,” wrote one fan.
“Billie is grown enough to know how weird and creepy this is” commented another.
“It’s not funny or chic, it’s not poking fun, it’s disturbing, and the adults in her life are letting her down once again.”
Following Billie's controversial Instagram post, the couple publicly debuted their romance on the red carpet on November 8 at the 2022 LACMA Art + Film Gala in their coordinated Gucci pyjama-style ensemble.
Shortly after their red carpet debut, Billie spoke publicly about her relationship with Jesse for the first time.
"I managed to get my way to a point in my life where not only was I known by a person, that I thought was the hottest f****ing f***er alive, but [I] pulled his ass... Jesse Rutherford everyone.... I locked that f***er down," she told Vanity Fair.
In December 2022, Billie and Jesse donned another couple's costume to celebrate Billie's 21st birthday, with the pair co-ordinating as Mr. and Mrs. Claus.
Keeping their relationship out of the public eye, Billie and Jesse only shared a handful of photos together throughout early 2023, with the couple making their last red-carpet appearance together in March at the 2023 Vanity Fair Oscars afterparty.
Two months later, the couple announced that they had split after less than one year together, with a representative for Billie confirming the breakup to People.
"We can confirm Billie and Jesse did split amicably and remain good friends. All cheating rumours are false. Both are currently single," the statement read.
Following their split, Billie took to her Instagram in August 2023 to respond to fan queries regarding her relationship with Jesse, with the star stating they are "very very good friends only," before calling Jesse "my homie forever."
While the conversation surrounding Billie and Jesse's relationship may have left headlines shortly after their split, Billie sent fans into a frenzy in later October when she was photographed holding hands with Jesse's ex-girlfriend Devon Lee Carlson as they attended Kendall Jenner's Halloween party in Hollywood.