Alone again, Terry took up ballroom dancing with Viv Windsor, the wife of his best friend Vic, as his partner. After a while they began sleeping together and when the truth was revealed he was forced to let Viv and Donna move into the Woolpack. The situation was unhappy for all involved and the relationship quickly fizzled out - with Viv going back to her husband in the end.
Terry’s tenure at the Woolpack came to a violent end in 1998 when he slept with Alan Turner’s granddaughter Tricia Stokes, only to discover that Scott Windsor was doing the same. When he exposed Tricia as a woman with loose morals in front of the entire pub, Alan punched him in the face and sacked him.
In 2000, Terry began to work for Chris Tate and the two men developed a very deep friendship. Meanwhile, Terry was starting to fall in love with Woolpack barmaid Louise Appleton. However, she didn’t feel the same way and began dating businessman Ray Mullen. When Louise became the target of a stalker, she thought Terry was the culprit - but it was actually Ray.
When the truth was revealed on Christmas Day 2002, Louise had a scuffle with Ray and accidentally killed him. She called Terry for help and the two of them covered up Ray’s murder. Thinking their relationship had developed, Terry tried to kiss Louise but she rejected him and he left Emmerdale to go on holiday to Spain and stay in his good friend Bob Hope’s ex-wife’s hotel.
While in Spain, Terry fell head-over-heels in love with Bob’s daughter Dawn and returned to Emmerdale with her. The couple become engaged and both Bob and his ex-wife were horrified. Despite objections, the two married and soon Dawn was pregnant with their first child. However, just hours after baby T.J. was born, Terry suffered a stroke and was left close to death. He clung to his life though and for the next year Dawn had to nurse Terry back to health. The situation took its toll on their relationship and Terry was heartbroken when Dawn left him for Scott Windsor. After a brief custody battle over T.J., Terry and Dawn’s relationship improved and life was more stable for the entire family.
In the meantime, Louise discovered that she did have feelings for Terry and they finally got it together. They’re so happy they decide to buy the B&B from Alan Turner and go into business together. However, Louise can’t resist when sexy businessman Matthew King makes it clear he wants her and the two begin having a passionate affair behind Terry’s back. It goes on for weeks and Terry only finds out when Louise breaks up with him just as the deal for the B&B goes through. He’s left distraught and raging so when Louise – who is quickly dumped by Matthew – begs for a second chance Terry tells her to clear off. Instead, he throws himself into work and takes a job at Tom King’s as his chauffeur. When his pal Bob Hope gets married, Terry is surprised to find himself spending the night with his ex-mother-in-law Jean. They agree it was a one off and move on but fate is about to throw them back together. Both Terry and Jean are devastated when Dawn is sent down for benefit fraud and the trauma brings them together. They begin a secret affair and its clear they are falling in love. Desperate to keep the romance secret, Jean allows Tom King to believe he has a chance with her. But the whole scam is exposed when Jean and Terry are caught getting frisky in public and marched down the nick! When Dawn discovers what’s been going on, she hits the roof and insists it stops. But Jean refuses and Dawn retreats to Newquay to think everything over. When she arrives back, Dawn tells them she will put up with the relationship but plans to leave Emmerdale to start a new life in Cornwall. Hurt beyond belief, Terry threatens to sue for custody of TJ but backs down when he realizes he’s tearing the family apart. After Dawn's death on 13 July 2006, he is assumed to now have full custody of TJ.
In the aftermath of Dawn's tragic death the Hope family (led by Bob and Jamie) begin a campaign for revenge to avenge Dawn's death. Jean grew increasingly tired of Bob's campaign against their former employers and was trying to persuade Terry to talk some sense into Bob. When Tom offered compensation for Dawn's death and Bob refused, Jean went behind her families back and accepted the offer thinking of the money as a new start for grand son TJ. Jean then fled to the airport with TJ. Terry discovered Jean's deception and raced to the airport to stop her leaving with his son. However Jean managed to board her flight to Morocco and left the village for good.
Terry was devastated. He then became a prime suspect in the murder of businessman Tom King who he now blamed mainly for him losing his son to Jean as well as Dawn's death. Shortly after Tom's death Terry disappeared from the village. He arrived a few weeks later with TJ back! He was soon questioned by the police as a suspect in the murder investigation but was released without charge.
Terry's father, Duke arrived in Emmerdale in June 2007.