Neil Winter's attorney girlfriend Leslie Michaelson broke down and admitted the truth to Neil about her past, that her father, Gus, was in prison for killing her mother, and that she and her brother Tyler had changed their names as teenagers when they went to California to live with an aunt. Neil later stopped Leslie from leaving town after she received a call on her cell phone from Gus, and talked her into going to see Gus in prison. Gus was eventually cleared and released from prison, but it was not long before Gus died from a heart attack. After his death, Leslie found a saved packet of letters written to him from a woman named Rose.
After Neil's apartment was ransacked and memorabilia and a flash drive containing sensitive Jabot files were taken, a story about Leslie hiding her secret past hit the Internet on the GC Buzz page. When questioned about potential enemies, Neil could not think of any. Later another story about his daughter Lily and her husband Cane appeared which had come from Neil's stolen journal. Computer-hacker Kevin Fisher, who was assisting the police, tracked the uploads from a computer in the Genoa City Athletic Club's business center.
When a story about Neil's son Devon hit the GC Buzz, Neil posted an open letter there daring the attacker to identify themselves and take Neil on in the open. Leslie realized that a phrase used in the Lily story was a variation on the line "I don't want realism, I want magic." from Streetcar Named Desire, which had also been used in one of Rose's letters to Gus, and felt it was no coincidence.
Inside the safety deposit box of Gus, Leslie and Tyler found a will giving Rose half of Gus' estate and photos of their mother, themselves, and one of Rose which was signed, "I haven't forgotten. I never will." A reply to Neil appeared on the GC Buzz: "How easily you seem to have cleaned up your mess, and swept it all away. I haven't forgotten. I never will." Leslie noted the similarity in the signature line on Rose's photo. So Neil responded, "You've gotten my attention with pointed remarks, like a thorn on a rose." to see what it might stir up. The reply was "You are not so perfect. What would your children or grandchildren think of you if they knew what you'd done?"
Leslie then discovered that Rose died in 2007 in Evanston, IL, from a stroke, and that Rose had a daughter, Ann Turner, who had left the country after her mother had died. Leslie was trying to track her down.
Neil later remembered that he had been in Evanston that year during his alcoholic period, and met a woman named Rose in a bar. Neil and Leslie went to the bar where the bartender indentified Rose's photo. He also remembered how Neil had rescued Rose's stolen purse and subdued the purse-snatcher, how they had left together, but said that he had never seen either of them again. Leslie suggested hypnosis, which made Neil remember that they had talked about his kids and her daughter Ann, that after he caught the purse-snatcher, Rose had kissed him as a reward. They left the bar together falling-down-drunk as he gave her his business card, and they ended up at a hotel. But Neil also recalled that after Rose passed out, he had put a "do not disturb" sign on the door and left. But when Neil told Leslie about it, they put it together that this happened the night that Rose died April 15, 2007.
Feeling guilty, Neil confessed to the police who felt that no crime had been committed. Neil followed the detective's suggestion that they bait the blogger telling them that he knew what he did, and wanted to meet and explain the truth. The response called him a murderer, saying they would not back down until he lost everything just as they had. Neil decided that the blogger had to be Ann Turner, and despite Leslie's insistence that the blogger had to be in Genoa City, Neil took off for her last known address in London. Viewers then saw Cane's assistant Hilary Curtis staring at a photo of Rose, and realized that Hilary was Ann Turner. Neil returned with information that Hilary had been working for a successful financier, but had suddenly quit the day that Gus was released from prison. In Ann's belongings left behind, Neil found his old business card and some newspaper clippings, one announcing that Leslie had joined Jabot and was working for Neil. Meanwhile, Hilary told her boss Cane how her mother had gone through hell, and she had died alone, and that Hilary should have been there for her. Neil gave Kevin the phone number Ann had called repeatedly from London which Kevin tracked back to Newman. Then viewers saw Hilary arrive home and kiss a half-naked Mason Wilder, who formerly worked at Newman and modeled for Jabot. Mason had been her accomplice. Cane and Lily discovered that Hilary was Ann, and told Neil. Neil met with Hillary and explained what had happened between him and her mother, Rose. He assured Hillary that he was not interested in punishing her, but asked her to stop punishing him. But after they parted, Hillary played his confession to the GCBuzz, and it was published that Neil was responsible for Rose's death.
Neil again tried to reason with Hilary, finally telling her that he deserved her anger, to go ahead and hate him, but to stop hurting the people that he loved who were innocent. They sat down and had a heart to heart about how close she had been to her mother, the shock of her death causing Hilary to leave school and the country, desperate to forget. Neil offered to start a memorial in Rose's name or a college scholarship. Hilary agreed and toasted to a fresh start between them. Neil was pleased until he realized there was vodka in the orange juice she had given him, and spit it out. Hilary admitted to trying to get him drunk, just like he had done to her mother. Neil gave up, and left. Determined to put an end to it, Devon offered Hilary a million dollars to go away and leave them alone, but she turned it down. Mason overheard, got mad and walked out, realizing they were not partners, and that she had just been using him.
Leslie intervened and gave Hilary the old letters that Rose had written to Gus. After reading them, Hilary apologized to Neil for tormenting him and his family, saying that she knew in her heart that Rose had been drinking ever since Hilary had left for college. Hilary admitted that she had been caught up in grief, and what she had done to his family had not brought her mother back nor made the ache in her heart go away. Neil forgave Hilary, and Hilary reminded Neil that it was time he forgave himself for Rose's death as well. Believing Hilary to be sincere, Neil offered her a job at Jabot as assistant to CEO Jack Abbott. When Jack heard the story, he took up for Hilary against the rest of the Winters family who still did not trust her. The always efficient assistant, Hilary soon became Jack's sounding board and friend. Devon began hanging out with Mason, and dismissed Hilary's warning not to trust him, while Mason continued make charges to a duplicate of Devon's credit card.
Stuck in an elevator together, Jill showed Hilary the music box she had inherited from Katherine, and in chatting, discovered they had similar roots; their families being abandoned by their fathers when they were very young.
Hilary tipped Devon that Mason was the one who had stolen his identity. Devon slugged Mason, accused him, and told him to stop lying as he was about to prove it. Later Mason threatened pressing assault charges. Although the security footage had only shown the back of someone's head, Devon bluffed Mason that they had a great shot of him checking into the hotel, plus handwriting analysis, which sent Mason fleeing.
When Devon heard that the athletic club was for sale, he bought it. Cane agreed to become the business manager, and Lily the club manager. Lily's first act as manager was to kick Hilary out, but Devon stood up for Hilary and got her a suite instead.
Thanks to some effective sleuthing by Hilary, she and Jack discovered that Bonaventure Industries had become profitable by selling diet drugs illegally online only after Victor took over Chancellor and control of Bonaventure. After Summer nearly died from taking Bonaventure's VivaSurge, Jack knew he had the means to get back at Victor.
Devon agreed to underwrite the Delia Project fund raiser that was to be held at the athletic club. Lily was resentful when Hilary came up with a fairytale theme "Once Upon a Winter's Evening". Devon was impressed with her creativity and asked Hilary to help. Lily was shocked to realize that Devon liked and was attracted to Hilary. Neil approved and said he felt confident that Hilary had changed, so Devon finally asked her to have dinner with him.
Jack attended the Delia Project Valentine's Day benefit, calling Phyllis to say good night and wish that she were there with him. Hilary adjusted his tie and kissed him, backing away embarrassed. She later apologized to Jack for being so forward.
Neil and Hilary were appointed by Jack as liaisons between Jabot and Forrester Creations for the promotion of the Chelsea line, but Lily refused to work with her on the fashion show. Hilary and Neil traveled to L.A. to meet with the Forresters, and began to enjoy each other. They ended up making a bet on the outcome of the basketball final 4, even though Hilary disliked the game. Then for fun they attended a television taping of 'The Price is Right', where Hilary won $12,500. Upon their return, Neil was shocked to find out that Leslie had gotten married to a doctor she had known online for only three weeks. Neil took it very hard, doubting that she had ever loved him. Hilary told him that he was lucky she had set him free, that it was not meant to be, and reminded him that she knew his history of spending years chasing the wrong women. Neil, in trying to explain what real love is, ended up kissing Hilary. He said that if only they had met at another time.
The fashion show was held using real women of Genoa City as models, Lily, Hilary, and Abby alongside Esmerelda the featured model for the line. Lily insisted on bickering with Hilary throughout, but the fashion show was a hit. Devon accidentally walked in on a half-dressed Hilary as she was changing for the show, and was impressed with what he saw. Afterward, Hilary berated Leslie for breaking the heart of a good man like Neil. Leslie accused her of wanting Neil for herself. Later, when Neil kissed Hilary again, she backed away saying that he was only on the rebound, and her number one rule was to not get involved with someone she worked with. But she succumbed to his advances and they made love. Afterward, Hilary felt that it should stay a secret due to the way his family still felt about her.
Many sexual rendezvous later, Neil suggested taking their relationship public, and telling Devon first, but Hilary reminded him that the gossip rags would have a field day with it. But Devon saw them kissing as Neil left her room and confronted Hilary, calling her a gold digger. Joining Neil, Lily and Cane in the GCAC dining room, Devon announced that Neil was sleeping with Hilary. All were shocked. Hilary joined them, and Lily tore into her. Hilary left, Neil made his choice, and followed her. He then told Hilary that he loved her, and she admitted that she felt the same way. Tired of the flack from Lily and Devon, Hilary packed her bags to move out of the GCAC. Neil intercepted her on the way out, and announced to a shocked Lily and Devon that she was moving in with him.
At the family father's day celebration, Lily tried to shame Neil into dumping Hilary by telling him that his son Moses would be going to kindergarten this year, and other people would tease him because his father was living in sin with a younger woman. Neil decided Lily was right, and asked Hilary to marry him instead. Hilary accepted, and Lily was appalled when she found out. Neil decided they would get married the next day. So Devon met Hilary in the park and told her he thought she would be better with him and kissed her. Hilary admitted there was a connection between them, but it was too late, that Neil was fulfilling all her dreams she was committed to him. Neil and Hilary were married in Chancellor park, and only Devon showed up to be his best man. Hilary hesitated her I do, looking into Devon's eyes, but went through with it. Devon wished them the best, and to be happy. But Devon drank all night and cornered Hilary in the elevator the next day trying to tell her how much he loved her. Hilary told him to sober up and shut him down. Then Hilary went to Neil and told him she wanted to have a baby. Neil assured her there was no rush.
Marriage did not keep Lily from continually snarking at Hilary, in fact she even pushed Hilary into the GCAG pool. Neil shamed Lily in front of her kids and told her to grow up and get over it. Devon took Hilary to a room, told her to take a relaxing bath while housekeeping took care of her clothes. Devon bought her some clothes when Lily made Hilary's clothes "disappear". Devon and Hilary went to the laundry to look for her clothes, where he told her that he was leaving town for however long it would take to get over her. Hilary tried to talk him out of it until Devon kissed her, and passion overtook them as they started tearing at each others clothes. Cane spotted them and made a noise to interrupt them. Cane later told Hilary that he knew about them, and suggested to Hilary that if she had feelings for Devon, she needed to break it off with Neil.