Little Lily was born in 1995 to Neil and Drucilla Winters. Or so they thought. It was revealed years later that the tot’s biological father was actually Neil’s brother, Malcolm. Surprise! At least he saved a fortune on the cigars that he never passed out.
At just 15 years old, Lily (by then Christel Khalil) met Kevin, who was 20, through an online chat room. He eventually convinced her to hook up, after which she found out that she had a sexually transmitted disease. So yeah, deal-breaker on top of deal-breaker.
Daniel Romalotti was the first real love that Lily (then Davetta Sherwood) had. It… uh… it didn’t go super well for them.
Daniel and Lily’s parents were so opposed to them being together that they would often meet in secret. Phyllis and Danny’s son and Neil Malcolm and Dru’s daughter even ran away together!
Lily’s BFF at the time was Colleen Carlton. Well, until she met her maker as a result of one of Victor Newman’s plots against Jack Abbott. Ironically, The Mustache ultimately received the no-longer-needed heart of the deceased. (At least now we knew that he had one.)
Daniel and Lily (Khalil again) couldn’t stand being kept apart and fled to Los Angeles. It wasn’t long, though, before Nick, Phyllis, Neil and Dru found them and brought the kids back to Genoa City. Curses, foiled again!
When Drucilla heard that troubled teen Devon Hamilton had a background similar to her own, she took him in, and eventually, Neil and Dru adopted him, giving Lily the brother she’d never known she wanted.
Lily was always close to her Uncle Malcolm. And when the truth came out that he was her biological father, she was the one to break the news to Neil.
Cane Ashby was 31 when the much-younger Lily started falling for him. Though he tried to deny his feelings for her, it was futile. In the end, they embarked on a full-blown romance blissfully unaware of the bumpy road that lay ahead of them.
While on a break from Cane, Lily gave Billy Abbott (then Billy Miller) a shot, but nothing came of it. Little did they know that they would reconnect in more than one respect later on in life! (He just had to change… a lot!)
After Cane and Lily became pregnant with their first child, she unfortunately miscarried. The couple weathered the disappointment, but there was an even bigger storm ahead. Sigh. There was always a bigger storm ahead for those two!
Lily was diagnosed with ovarian cancer and underwent chemotherapy. Before surgery, she harvested her eggs, which were used to conceive twins Charlie and Matilda, who were carried to term by pal Mackenzie Browning.
Soap-opera rapid-aging syndrome hit Lily’s family hard when Charlie and Mattie were matured overnight from youngsters to older teens. Age-appropriate drama ensued, particularly for Mattie, who fell for Victoria Newman and J.T. Hellstrom’s son, Reed.
During one of the “bumps in the road” of her marriage to Cane, Lily hit the sheets repeatedly with Joe Clark. She later felt foolish when she discovered that he had set out to destroy her marriage. It got worse: Joe went to jail after confessing to setting Cane up. Poor Lily. She sure can pick ’em.
Lily worked the camera off and on from the time she was young and was the Fresh Face of Jabot. When a poser didn’t show up for work on a Brash & Sassy shoot, Lily joined the team, which had her working with Billy (now Jason Thompson) and Cane, who became embroiled in a scandal with PR rep Juliet Helton. In other words, Lily’s man got Juliet pregnant.
Devon’s true love, scheming Hilary Curtis, was arguing with Lily when she ran a red light and was hit by another car. In a flash, Hilary and her unborn child were gone, and Lily was sentenced to 12 months in prison. Her marriage to Cane might have survived, but he just couldn’t keep from kissing Victoria.
Lily was crushed when Neil died in his sleep from a stroke. She stood before family and friends at his funeral and honored the man who raised her.
Billy’s mom, Jill, was able to persuade Lily to return to Genoa City after her release from prison. She floated the idea of Lily and Billy teaming up to run Chancellor Industries’ new media division, Chancellor Communications. It turned out better than Jill could have ever hoped when, after first butting heads, the pair later fell in love on the job!
Lily moved in with Billy, and although Chance Comm became a casualty of the gambler’s penchant for risk-taking and his issues with Adam Newman and Ashland Locke, Jill stunned them both by making her son’s honey CEO of Chancellor Industries. Someday, maybe they could even afford a bedroom!
After becoming CEO of Chancellor Industries, Lily wasted no time trying to impress Jill and making her mark. She called a meeting with Devon and proposed a merger of CI and Hamilton-Winters, which he was reluctant to agree to despite his sister’s insistence that Neil would want it. Devon later signed on the dotted line, and the pair offered an executive position to cousin Nate Hastings as well!
Combined with Billy’s inability to keep any relationship afloat for long, his keen interest in acting as a support system for old flame Chelsea Lawson brought his romance with Lily to an end.
When it rains, it pours. At the same time as Lily was dealing with her break-up from Billy, Devon was, in a way, dumping her, too. He wanted to pull out of the CI/Hamilton-Winters merger — by any means necessary.
On the plus side, Lily suddenly had back in her life her first husband, Daniel. Older, wiser and conventiently free of girlfriend Heather Stevens, he was just what Lily needed to put a smile back on her face. Not here, obviously, but you know… in general.
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