Soon after EJ DiMera was shot, Kate came to Philip and asked him to hide her gun for her, since she was a suspect in his shooting. As a favor to Belle, Philip arranged for Shawn to find Kate's gun in the alley behind the Brady Pub, since retrieving the evidence would further his career in the police department. In exchange, Philip asked Belle to spend one evening with him. Belle complied and met him at the hotel by the airport and confessed that she was in love with two men. Philip realized the difficulty he was imposing on her life and decided to let her go. He was stunned when he encountered his old flame, Chloe Lane Black, just outside his hotel room. They shared a drink together and she told him that she was now divorced and her career as an opera singer didn't pan out.
Chloe appeared interested in Philip again, but it was obvious that he only had eyes for Belle. Philip even challenged Hope to tell Shawn the truth about his affair with Belle. He and Chloe nearly made love at his Titan office during Christmas of 2007, but he ended up rejecting her and throwing her out. Afterwards, Philip did some research on Chloe and discovered that she was wanted by the Vienna Police as a person of interest in the case of her missing husband. Additionally, he found that Chloe was never divorced nor legally separated from Brady. He confronted Chloe with the information and she confessed that she and Brady got into a huge argument before he went missing, but swore up and down that she had nothing to do with his disappearance. She begged him for his help, revealing that she really came to Salem because she needed someone's help who had money, power, and connections. Philip agreed to secure her freedom using his connections if she agreed to get close to Shawn.
Shortly after the new year in 2008, Philip stood by his half-brother Lucas's side after he was arrested for the attempted murder of EJ DiMera. He urged Lucas to plead temporary insanity and fight for his freedom, but his pleas fell on deaf ears. During this time Belle also confessed to Shawn that she slept with Philip. After Belle and Claire were kidnapped by psychic Crystal Miller, Philip jumped into the cold water and saved Belle. He still professed to love her and kept vigil by her in the hospital.
When Belle was recovered, Philip, Chloe, Shawn, and Belle took the Kiriakis jet to Ireland after a clue indicated that Claire had been taken there. Philip and Shawn decided to call a truce. The foursome met other Salemnites there and were reunited with Claire. It turned out that Colleen Brady had arranged for the kidnapping, believing that Stefano DiMera was after them. Philip and Chloe grew closer during their time in Ireland and commiserated over their lost loves. On the way back, several Salemites lives were endangered when John Black's private jet was sabotaged. Philip comforted a hysterical Chloe the whole time their lives were at stake. Grandpa Shawn heroically died after giving up his oxygen mask for Bo. The plane crashed in Greenland and crushed Philip's prosthetic leg. While awaiting rescue, Philip and Chloe nearly made love in the tent, but decided to refrain from doing so.
After arriving back in Salem, Philip invited Chloe to stay at the mansion. He secretly recorded her German phone conversation, as he was still suspicious whether or not she had anything to do with Brady's disappearance. He discovered that she threatened Brady, But Chloe insisted that the threat was taken out of context.
In March of 2008, Philip mended fences with his half-brother Bo after he nearly died from pancreatic failure. He also shared one final tender moment with Belle after she announced her plans to sail around the world with Shawn and Claire.
Philip has since turned his attention to Kiriakis Shipping, as a money hungry John Black has taken control of the DiMera empire and has bribed a customs official to hold all Kiriakis shipments. He has also taken notice to the custom official's daughter, Morgan Hollingsworth. Will Philip find love with Chloe, Morgan, or perhaps another woman and smile again? Stay tuned!
