During the third series, Tom and Diana get together as a couple after a one-night stand, though Diana is far more casual about the new state of their relationship, much to the chagrin of Tom, who wants a committed relationship. In series four, Diana's financial situation collapses and Tom discovers that his room is infested with damp. Tom forces Harvey to upgrade him to a new apartment in Bayview and allow Diana to live with him as his lady friend. By series five, the two become engaged along with Harvey and Jane, who first get together as part of a cynical scheme to get Harvey accepted into an exclusive country club. When the plan fails, and Jane responds by quitting her job to begin the process of becoming a nun, Harvey realises that he has come to enjoy Jane being in his life and the two go through with their vows. But Diana gets cold feet regarding her impending marriage to Tom (much to her niece Sarah's shock). Tom discovers this before the wedding and saves Diana from having to either go through with the wedding or have her niece sever all ties with her aunt, by calling off the wedding just as the two were about to say "I Do".