Timothy is preparing for a job interview but has a recurring dream that the interviewer is his old headmaster, who wants to cane him. He visits a psychotherapist who tells him not to worry but to enjoy the experience of the interview. Unfortunately he enjoys it rather too much with an overly laid back attitude. And those dreams still persist with Mother replacing the headmaster.
Timothy is not pleased when his cousin Brinsley, who bullied him as a child, comes to stay, especially as Mrs Lumsden gives him preferential treatment, banishing Timothy to the attic to give Brinsley his bedroom. In fact she even tells Timothy to move out though fortunately the constant fussing over him is too much for Brinsley, who makes his own decision, thus negating the need for Timothy to emigrate.
When rich Aunt Esme visits the family Timothy and his father are so embarrassed by Mother's attempts to get Esme to leave her her money they sneak off to the pub but prang the car in the process. A shifty garage owner mends it at cut price, thanks to aunt Esme, but since Mrs Lumsden has reported the car stolen the police give chase and there is a second accident before Timothy learns who will benefit from the will.
Frank is getting married to Jennifer but has asked his friend Richard to be best man - to Timothy's annoyance. However, after Timothy has indirectly caused Richard to break a leg, he gets his request with Mrs Lumsden inviting the happy couple to tea. Timothy decides to sabotage the occasion though ironically he is the one who also ends up with a broken leg.
The night before Frank's wedding Timothy meets and gets on extremely well with bridesmaid Liz, who also has a restrictive family life and is accident-prone like himself. Next day Timothy has to come to her aid but, as best man, has to get the ring to the church on time, and almost fails to make it due to a succession of mishaps. On arrival he encounters disappointment and a lucky escape both at the same time.
The town is gripped by gold fever when the local paper prints a series of cryptic clues which, when linked together, will lead to the site where a golden rabbit has been buried, the first to find it winning three hundred pounds. After helping Frank Timothy decides to enter the contest himself and, whilst he fails to win the prize, he does get to meet the delightful Winifred - or Freddie to her friends.
Muriel and Kevin invite Timothy and Freddie to stay the weekend with them to help their romance along but when Timothy's dreadful mother finds out she pretends to be dying to coax Timothy back home. Oddly enough, despite his weakness, Freddie is still happy to go out with him and they plan a trip abroad.
When the mobile library breaks down in the country Timothy takes shelter from the rain in a barn where three elderly women tell his fortune. Although Muriel dismisses it all their prophesies come true so that when they foretell a successful job interview with a move to Yorkshire Timothy knows the job is in the bag. Sadly once again he had reckoned without his dreadful mother.
Timothy is obsessed with the fair Jean from Acacia Avenue but is too cowardly to approach her. On Mrs Lumsden's birthday she is predictably ungracious about the family's presents but delighted when Timothy arranges a day on the river with her ukulele-playing old friend Edgar. Typically it rains and things go from bad to worse as Timothy literally goes overboard in front of Jean.
After an accident at the tennis club Timothy is taken to hospital where he wrongly believes that he is terminally ill. As ever Mother is too bound up in her own selfish world, Father more concerned in ridding the garden of moles and the people at the pub more interested in the Colorado beetle in the sausage roll to listen to him. At least he can dream that he had an heroic funeral with a glamorous mistress among the mourners. But then he wakes up.