Kelly Andrews moved from St. Louis, and had not been living in Genoa City long when she met Billy Abbott at a grief counseling session. Billy shared with her that he had recently lost his seven-year-old daughter, Delia, to a hit and run driver, and the guilt he felt for leaving her alone in the car. Kelly could relate, as her seven-year-old son, Sam, had been killed while riding the bicycle that she had bought him. Billy was married to Victoria Newman, who grieved with him for Delia, but Delia's mother was his former wife Chloe. Kelly told him that she and her husband had divorced after Sam's death, and Kelly had moved to Genoa City to get away from the memories. Kelly and Billy bonded, and appearing to get more comfort from each other than from the group, they began meeting alone instead.
Running into each other at Crimson Lights, it quickly became evident that Kelly and new Genoa City doctor, Ben "Stitch" Rayburn, knew each other from the past. Kelly commented, "She was going to find out anyway, it just came up, and wasn't intentional. I take it you and your wife are over?" Ben told her, "We are not going to talk about my wife. In fact, we are not going to talk at all."
After Victoria left for the airport to spend Christmas with her son, Reed, Billy ran into Kelly who was crying and alone on Christmas. Billy took Kelly home to her apartment and in a weak moment, they ended up having sex. After Victoria's flight was grounded by weather, Billy arrived home to find her there, and guiltily promised to change and never let her down again. The next day he gave Victoria roses, and she was so delighted that when she ran into Kelly later, she invited Kelly to dinner. Then Victoria included Dr. Ben when he dropped off her lost cell phone. The get-together became very uncomfortable for everyone but Victoria. When Victoria brought down baby Johnny, Kelly got emotional and left, and Dr. Ben left soon after, leaving Victoria and Billy to have dinner alone.
The next day Billy met with Kelly where she worked at GC Cares, and Kelly asked him to become the director of the Delia Project which was being funded by an anonymous donor. After telling him that his mother Jill had agreed to be on the board and had suggested him as director, Billy accepted.
Dr. Ben caught Kelly coming out of Billy's hospital room after Billy was involved in a car accident, and he accused Kelly of sleeping with Billy. Kelly admitted it had just been once, a mutual sharing of their losses. Ben warned her not to let it happen again. Kelly lashed out at Ben, calling him Benji, saying that she was not the reason his wife wanted nothing to do with him, that their relationship had finished before it started. Then referring to Adam Newman's apparent hit and run of Billy's daughter Delia, said, "Who could do something like that, then just go on with his life?" That comment seemed to have struck a nerve with Ben.
Billy and Victoria attended the Delia Project Valentine's Day benefit, as did Kelly representing GC Cares. They all ended up being taken hostage in a botched robbery attempt by Richard Womack. Womack fired at the chandelier, which fell on Billy, injuring him. Then when Billy tried to jump Womack, he kicked Billy, breaking some ribs. Victoria cradled Billy while Kelly tried to administer first aid. Billy began babbling, apologized, and confessed to sleeping with Kelly. Victoria told Kelly to get her hands off her husband, slapped Kelly, and called her a tramp. After everyone was released in an exchange for a plane to escape, Colin Atkinson jumped out from where he had been hiding, and Womack was killed as he and Colin struggled over the gun.
After Billy and Kelly's one night stand had been exposed, Ben became concerned for Victoria, and while consoling her they ended up kissing. Victoria admitted it to Billy, and Billy warned Ben to stay away from his wife. But when Victoria found out that Billy had gone to console Kelly, she accused him of putting Kelly first and kicked him out. Since Billy had made it clear that he still wanted his marriage, Kelly lamented to Ben how sad and lonely she was. Ben told Kelly that she could have him now that his wife was divorcing him. Kelly said that there would be no forgiveness for what he had done. Kelly claimed that she could not get over Billy, so she was leaving her job at GC Cares to avoid him. Finding out that Ben had kissed Victoria, Kelly commented to Ben that Victoria would not want to be involved with a murderer. She later reminded Ben that he had killed a man, and that he had already told Billy that he had done something unforgivable in his past.
Lily Ashby came up with an idea to boost the athletic club's post-Womack slump by suggesting Jabot premiere Chelsea's new fashion line there with a fashion show. Having made friends with Kelly, Lily hired her to be her assistant during the show.
Billy's brother, Jack, agreed to give Billy a place to stay, and in trying to help his situation, Jack invited Kelly to dinner and tried to pay her off to leave town, but she tore up his big check. Realizing that Kelly was a better person than he had assumed, Jack tried to form a truce with her, and convince her to go to dinner again. Jack, whose wife Phyllis had been in a coma for eight months, realized that after working with Kelly and running into her now and then, he was finally beginning feel good again. Thinking that maybe it was time to give up on her, Jack checked in on Phyllis, but there was still no progress. Jack ran into Kelly again and he took her with him to a Vivaldi concert in the park, where they began quoting old movies, and realized they had the same old favorite in "Vertigo". Jack kissed her and asked her on a real date.
Billy confronted Stitch, telling him that he intended to find out what Stitch did not want anyone to know from his past. Stitch told him to look all he wanted, that he would not find a thing, so Billy began searching the Internet. Ben asked Kelly not to tell anyone about his past. And Kelly, who was now happily hoping to get a teaching position in the fall, and falling for Jack Abbott, agreed that they had both destroyed each others lives, but it was time for them to forgive and move on.
During their real date, Jack and Kelly kissed again and decided to get a room at the athletic club. Kelly was waiting in some sexy lingerie, but when Jack arrived, fresh from an encounter with Summer, he called it off, feeling disrespectful of Phyllis. After Noah spoke to Summer, Summer told Jack that she really could not begrudge him a life other than waiting for Phyllis to wake up. Jack told Kelly he wanted to resume where they left off, but Kelly decided that she did not want to be hurt when Phyllis woke up one day.
As a favor for Chelsea, Jack showed up to meet a new tenant for a condo that Adam owned, and found it was Kelly. She accused him of stalking her, and Jack said he felt it was fate throwing them together. As she was about to leave, they heard a violin next door playing Vivaldi, and Jack asked her if she still did not believe in fate. Kelly took the apartment, and moved in to find vases of flowers and a picnic arranged on the floor. Jack arrived shortly afterward and got her to talk about herself. She spoke about how her father died when she was in college and devastated her. How she married hastily for some stability, then had Sam, who died and devastated her again, and resulted in divorce. Jack and Kelly began dating, and Jack was elated to find that he could be happy again. Summer became upset that Jack had given up on her mom, but she said she understood that he could not wait forever, and would try to accept Kelly. Jack and Kelly christened Kelly's new place by making love.
Kelly, in speaking with Ben again, referred to him as "a man who doesn't even exist" and urged him to tell Victoria the truth about his past. She also said that Ben had taken away someone she loved, then when Sam died, she had lashed out and told Jenna about it. Ben decided to break up with Victoria, but they ended up making love instead. Later, Ben told Kelly that Victoria's husband Billy had gone to see his ex-wife Jenna, and that he could not bare to lose anyone he loved again. Kelly hugged Ben and assured him that through it all, she still loved him – while Jack looked on. Jack later confronted Kelly about her relationship with Ben, assuming they had once been lovers. But Kelly surprised him by admitting that Ben was actually her brother. Kelly explained that Ben had done something unforgivable, so she had cut him out of her life for years. Although Ben had reached out to her after her son Sam died, Kelly felt it was unfair that Ben was happily married while she had lost everything, so she told Jenna what Ben had done, and it had broken up his marriage.
Kelly shared with Jack that she came from a poor family, attended boarding school on scholarship, and got straight A's. Jack finally got Kelly to tell him Ben's secret, that her brother had murdered their father, their mother had taken Ben's side, and that he had served his time for it. She said that she had forgiven him, he was a doctor saving lives now, and felt that Stitch deserved a chance to start over. So Kelly hoped that Jack would not tell Billy. Jack did not, but Billy confronted Stitch with the truth in front of Victoria, Kelly, and Jack, and was shocked to discover that Jack and Kelly had known and not told him, so told them they could both go to hell. Later, trying to defend his not informing Billy, Jack admitted to Kelly that he was in love with her. Kelly rebuffed him, but later after realizing that Jack was the best thing to ever happen to her, she joined him in his bed and admitted that she loved him too.