Born June 25, 2010
Morphed into teenager May 24, 2017, said to be fourteen
Student at Walnut Grove Academy
House at 1101 Lavetta Terrace
Lily Ashby (mother)
Mackenzie Browning Helstrom (surrogate mother)
Cane Ashby (father)
Drucilla Barber (grandmother; presumed dead)
Genevieve Atkinson (grandmother; presumed dead)
Malcolm Winters (grandfather)
Colin Atkinson (grandfather)
Samantha Atkinson (aunt; deceased)
Caleb Atkinson (uncle; deceased)
Devon Hamilton Winters (uncle by Neil's adoption of Devon)
Moses Winters (uncle, son of Neil)
Nathan Hastings Jr. (uncle, son of Olivia)
Olivia Barber (great-aunt)
Neil Winters (great-uncle)
Lillie Belle Barber (great-grandmother)
Walter Barber (great-grandfather)
Mamie Johnson (great-grandaunt)
Zoey (dated, kissed)
Lily Winters married the Australian Cane Ashby in 2009. He was twelve years older than Lily. Lily became a model for Jabot Cosmetics, and Cane was a bartender at her father's club, Indigo. After one miscarriage, Lily was diagnosed with ovarian cancer and had a hysterectomy. Luckily, she had the foresight to harvest some of her eggs. Lily's best friend, Mackenzie, volunteered to be a surrogate and soon became pregnant with twins Matilda and Charlie, who were born two months premature. Lily asked Mackenzie to be godmother to the twins, and Lily's adopted brother, Devon, became their godfather. Cane and Lily broke up numerous times, divorced, and remarried, mostly due to Cane's screwups and the lies he told to cover them up, usually aided by his father, Colin, and some infidelity on both sides. Except for the time that Colin kidnapped the twins and Cane faked his death, they still managed to keep a family atmosphere for the twins to grow up in.
During one annual Delia Halloween costume party benefit held at Top of the Tower, at a time when Lily and Cane were split up, Lily dressed as Cleopatra and her boyfriend Joe dressed as the devil. A fire broke out on the floors just below them, cutting them off from the floor where her children were having their own party. They were rescued from the roof by helicopter, and Lily was reunited with the twins, who had been led out the front door.
Cane agreed to return home for Christmas Eve and Christmas morning with the twins, staying in the guest room. Neil and the kids planted some mistletoe then got the Ashbys to kiss underneath it. Months later, Jill and Colin threw themselves a small anniversary party, and they staged a fight to get Lily and Cane to reconcile. Lily and Cane made love in a hotel room, but they decided not to tell kids that they were any nearer to reconciliation so as not to get their hopes up. They did eventually reconcile.
In late 2016, Neil was playing basketball with grandson Charlie, but by May 2017, Charlie and Mattie had morphed into teenagers and were sophomores attending Walnut Grove Academy. Charlie was popular and confident, and Mattie was smart, shy, and spectacled. Charlie got a summer job as a lifeguard at the Genoa City Athletic Club rooftop pool, and Mattie an internship at Hamilton-Winters Group. Charlie was very charming to the Athletic Club guests, especially one pretty bikini-clad woman named Juliet.
Earlier that year, Cane had gone to Japan where he and a coworker named Juliet had gotten drunk, and he'd gotten her pregnant; both were subsequently fired. Juliet filed a sexual harassment lawsuit against Cane, so the twins had to be told about their impending half-sibling, and they were shocked and appalled. When Charlie realized who his favorite customer Juliet was, he told her that if she were drowning, he would pull her out because it was his job, but he wanted nothing to do with her or her kid. After Lily discovered that Cane had used most of the twins' tuition money to pay off a blackmailer, Lily threw Cane out. Feeling guilty and hoping to win Lily back, Cane sold his car and paid the Walnut Grove tuition for the twins.
Meanwhile, young singer/musician Reed Helstrom was dating a fan named Zoey. Reed caught her kissing Charlie Ashby, so Reed and Zoey split up. Reed then became intrigued with Mattie. They began hanging out together when she could, and she would go to see him perform at the Underground. Finding out that her twin brother was Charlie, the guy who had broken up Reed and Zoey, and that Reed was the son of Victoria, who had fired his father, caused the two young men to bicker every time they met. However, once Mattie and Charlie discovered the truth behind Cane's firing, Charlie and Reed called a truce.