Young And Restless Rewind: Devon’s Love Life

Although never a reckless playboy, Devon Winters still experienced a robust love life before settling down with Abby and their son, Dominic. Now that the couple is betrothed, we look back at his romantic history, including that weird interlude with “Aunt” Tyra!

Roxanne (Tatyana Ali) 

An emerging businessman in 2007, Devon was dating a few girls casually and found sweet Roxanne especially charming. Both were virgins so their romance was for the most part quite innocent.

On his 21st birthday in 2009, Devon was surprised by the arrival of his mom’s sister Tyra and her daughter, Ana. Devon was disappointed when his married dad, Neil slept with Tyra, but that didn’t stop Devon from being deflowered by his “aunt” when he found out that they were not biologically related. However, Roxanne caught them together and walked out on Devon.

Roxanne and Devon made up and eventually consummated their relationship, which was pretty even-keeled until 2013, when Devon’s super-rich grandma, Katherine Chancellor died and left him billions. Mr. Nouveau Riche handed Roxy a debit card to buy whatever she wanted and while he expected that to be designer handbags and shoes, he was stunned to receive a fraud alert from his bank because of excessive spending. Knowing Roxy was behind the shopping spree, Devon accused his girlfriend of being a gold digger. Crushed, Roxy explained she had put down earnest money on a luxury condo for them to live in together. A rueful Devon begged for her forgiveness but Roxy was so hurt by his lack of trust that she walked out on him — for good.

In 2014, Devon found himself attracted to Hilary (check out this ICYMI interview with her portrayer, Mishael Morgan here), but he didn’t act fast enough on his feelings and she married Neil.

To try to forget Hilary, Devon started dating Esmerelda, a beautiful fashion model, in 2014 and even flaunted their romance by buying her an expensive car. Hilary stewed over the couple but covered her jealousy. The romance fizzled when Esmerelda kept dropping marriage hints and Devon realized she was more interested in his money.

2014 continued to be a busy year in Devon’s romantic life when he and his long-time friend went on a date. After, both decided they were better off staying platonic and four years later the besties partnered up to open a restaurant, Society.

Also in 2014, Hilary decided she wanted to be with Devon and proclaimed her love to him. But before she could tell Neil that their marriage was over, he was blinded in a freak accident and she refused to leave him. That may have been a noble sacrifice, but it didn’t stop Devon and his lusty stepmom from having an affair behind Neil’s back. In 2015, Neil’s vision returned just in time for him to catch Hilary in bed with his son. After divorcing Neil, Hilary and Devon wed, but the bride lost most of her memory after a mishap during their honeymoon and she thought she was still married to Neil.

In 2017, Devon was disheartened that Neil and Hilary had reconciled, so he started dating Mariah. They seemed to really enjoy each other’s company — until she was kissed by Tessa. Since Mariah now had the hots for Tessa, she came clean with Devon and they parted ways as lovers but remained close pals.

After Hilary’s memory returned, she and Devon decided not to pursue a relationship. She still wanted to fulfill her dream of becoming a mother, so in 2018, Devon agreed to be the sperm donor, and after Hilary successfully became pregnant, they fell in love again. Sadly, Hilary was critically injured in a car accident and she died right after she and Devon exchanged vows in her hospital room.

Still depressed over the loss of Hilary, Devon’s attention was caught by his sister, Ana’s cousin, Elena in 2019. While helping Devon through debilitating panic attacks and visions of Hilary, he and Elena became close and even started dating but Neil’s sudden death from a stroke in April was another emotional curveball for Devon. Luckily, Elena offered the support needed as Devon grieved for his father. Their relationship was building steam until an ambitious attorney entered their lives.

This hotshot lawyer came to town over problems with Katherine’s will. Even more shocking was that Amanda looked exactly like Hilary, so Devon found himself drawn to this stranger, alarming Elena. After the case of the will was cleared up, Devon asked Amanda to be the legal counsel for his and Nick’s charitable foundation, New Hope and she agreed. Later, a DNA test proved that Amanda and Hilary were twin sisters separated at birth. Elena confessed to Devon that her insecurity over Amanda drove her to sleep with his cousin Nate, and they broke up.

Also in 2021, Abby and husband Chance were having fertility problems so the solution was to implant her egg into Mariah after using another man’s sperm. Abby’s BFF, Devon volunteered his own little swimmers resulting in the birth of a boy, Dominic, in August. Chance had trouble bonding with his new son, while Devon reveled in fatherhood. In 2022, Abby and Chance were going through a rough patch, so she jumped in the sack with Devon, which her husband and Amanda walked in on. Not surprisingly, this broke up the two relationships with Dominic’s bio parents falling in love this time and becoming a couple. In 2023, Abby and Dom moved into Devon’s penthouse before they took up residency in the Chancellor mansion (at Chance’s insistence) and the following year, they became engaged.