Devon had no love for Hilary when she first came to town and tried to get revenge on Neil for his role in her mother’s death – he even offered her money to leave town. He softened toward her after she helped him out when his credit card was stolen and an underlying attraction between them grew.
Though Hilary fell into a relationship with Devon’s father, Neil Winters, their attraction was undeniable. They made love in Devon’s suite at the Genoa City Athletic Club.
Devon was between a rock and a hard place when he served as Neil’s best man while he married Hilary. Devon tried to convince her not to go through with it, but Hilary was committed and was drawn to the stability Neil represented.
Unable to deny their feelings for one another despite their best efforts, Hilary and Devon were drawn into an affair while she was married to Neil. She remained married as Neil had gone temporarily blind. Their tryst in the laundry room was stumbled upon by family member, Cane Ashby.
Neil regained his sight and realized Hilary and Devon were having an affair. He revealed all during a flight and the plane crashed. Devon stayed by Hilary’s side as she fought for her life while Neil went for help.
Hilary pushed Devon away as she recovered from the plane crash and was riddled with guilt. Eventually, they made their way back together and were finally married in a beautiful ceremony.
Devon and Hilary were having a great time on their honeymoon until tragedy struck. Neil showed up while Hilary was hiking, they argued and she accidentally went over a cliff. Devon was a suspect in her disappearance and presumed death. Meanwhile, Neil had spirited Hilary away and hired a doctor who used controversial protocols to keep her alive.
Devon ended things with Hilary due to her machinations and the aftermath had him leaving a gala in his new sports car. Driving too fast, Devon slid and wrecked. Since he didn’t remember breaking up with Hil, she was there for him as he recovered.
Devon and Hilary were often on the outs while she worked for him at GC Buzz. He even dated her nemesis, Mariah, which gutted her. Despite his new coldness toward her after she pulled schemes involving his family members, Devon was rarely out of Hilary’s orbit.
The end of Devon freezing Hilary out came after he agreed to donate sperm for her artificial insemination when she wanted to get pregnant. The pregnancy took but quickly ended, and Devon and Hilary made a baby the ‘old-fashioned way’, much to the chagrin of the woman he was dating. They soon got back together, Hilary moved into the penthouse, and they began planning for the arrival of their baby while also mentoring older teen, Shauna.
When the still-pregnant Hilary was on the brink of death in the hospital following a car wreck in a vehicle driven by his sister, Lily, Devon arranged to marry her in front of their family and friends. After they wed, Devon held Hilary in his arms as she took her final breath. Hilary’s ghost appeared to Devon several times after her death.
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