The History of Cane and Lily's Rocky Romance on Young and Restless

When Cane Ashby returned to Young and Restless by revealing himself to be the man behind the Aristotle Dumas alias, he not only expressed his desire to buy Chancellor away from Victor but also his hope that he and longtime love Lily Winters would reconcile. From their first meeting nearly two decades ago, Cane and Lily were swept up in a romance that lasted for years, and saw them navigate their way through multiple marriages, numerous affairs, and even his death. Lily isn’t interested in reuniting right now, but has their love story truly come to an end? Soap Opera Digest takes a look back at some of the ups and downs of Lily and Cane’s relationship to see why a reunion may or may not be in the cards for this Y&R couple.

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2008

Lily Winters (Christel Khalil), recently divorced from Daniel Romalotti, and Cane Ashby (then-Daniel Goddard), recently divorced from Amber Moore, met and were immediately smitten with each other. Though their age difference initially made them reluctant to pursue their feelings, the pair soon began dating.

Aaron Montgomery/jpistudios.com

2008

After Cane and Lily made love for the first time, she learned she was pregnant. Cane quickly proposed, but she declined, feeling they'd be marrying for the wrong reasons. Sadly, when the couple went for an ultrasound, the doctor discovered that the fetus had stopped growing and was reabsorbed into her body. Both Lily and Cane were heartbroken by the loss.

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2008

Chloe Mitchell (Elizabeth Hendrickson) set her sights on Cane and went so far as to get him drunk and convince him that they'd had sex. He refused to believe her and once again proposed to Lily, who finally accepted. However, she called off the engagement when Chloe announced she was pregnant and claimed Cane was the baby daddy.

Aaron Montgomery/jpistudios.com

2009

Lily met a guy on an Internet dating website who eventually turned out to be Billy Abbott (then-Billy Miller). They began seeing each other, which naturally led to Cane seeing green.

Aaron Montgomery/jpistudios.com

2009

After Chloe gave birth to Delia, she confessed that Billy was her daughter's real father, and Cane again proposed to Lily, hoping to gain custody of the infant. But Lily didn't approve of his actions and refused to accept until he gave up the lawsuit. Once he did, Lily and Cane were finally married in a beautiful ceremony on May 15, 2009.

sean smith/jpistudios.com

2009

The newlyweds' happiness was threatened by the revelation that Cane wasn't really Jill's long-lost son, but rather a man hired by Phillip Chancellor III to impersonate him. Still, when Lily was diagnosed with ovarian cancer, Cane was there to support her throughout her surgery and recovery, a journey that brought them closer than ever.

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2010

Before performing a hysterectomy on Lily, the surgeon was able to save some of her eggs, and Mackenzie Browning agreed to act as Cane and Lily's surrogate, helping the couple welcome their twins, Charlie and Mattie, into the world.

sean smith/jpistudios.com

2011

When Cane's father, Colin Atkinson, reentered his son's life, he brought with him some family enemies, and the resulting violence left Cane dead. Lily was devastated. She later thought she was losing her mind, seeing visions of Cane around Genoa City, but it turned out that he really was alive, and it had been his twin brother, Caleb, who had been killed.

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2012

Reunited once more, Lily and Cane invited their friends and family to a destination wedding in France and tied the knot on Valentine's Day, 2012.

Howard Wise/jpistudios.com

2013

Tyler Michaelson (Redaric Williams, r.) became smitten with Lily, and they grew close, but she ultimately rejected him in favor of staying faithful to her wedding vows.

Sean Smith/jpistudios.com

2013

A blogger targeting Lily and her family was revealed to be Hilary Curtis (Mishael Morgan), who wanted revenge because she blamed Neil Winters for her mother's death. Thankfully, Lily trusted Cane enough to let him seduce Hilary into confessing her schemes so they could put a stop to them.

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2015

When Cane kissed Lauren Fenmore, Lily retaliated by sleeping with Joe Clark (Scott Elrod). But when Joe was later revealed to be an extremely shady character who framed Cane for Hilary's kidnapping, she saw the light and reconciled with her true love.

ChrisD/jpistudios.com

2018

Cane was the one who strayed next, getting drunk on a business trip to Hong Kong and sleeping with coworker Juliet Helton (Laur Allen). She found out she was pregnant, but tragically died in childbirth, leaving Cane to raise their son, Sam, with Lily, who ultimately stuck by him.

Howard Wise/jpistudios.com

2019

After a car accident while she was driving left Hilary dead, Lily spent a year behind bars, which caused a divide between her and her husband. When she was released early from prison, Lily informed Cane that she wished to also be released from their marriage. Cane soon left town to track down the fortune Colin had stolen and return it to its rightful owner, Devon.

Howard Wise/jpistudios.com

2025

Lily was stunned when the reclusive billionaire Aristotle Dumas was revealed to be Cane (now Billy Flynn), especially when he seemed intent on reuniting with her. Lily made it clear that she was no longer interested, but Cane isn't one to give up without a fight. So what does the future hold for these two?

The Young and the Restless

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The Highs and Lows of Cane and Lily’s Rocky Romance on Young and Restless

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