When a drunk Mary tells Dick she once had a fling with his archenemy Vincent Strudwick, he is outraged and decides to get even with the pair of them by convincing Strudwick's wife to sleep with him. Tommy supports Dick's decision, imagining double dates - himself with Alissa and Dick with Strudwick's wife. Meanwhile, Sally gets the hots for Don after he starts riding a police motorbike, but the pair crash and Don ends up in full body plaster.
Dick crashes the car into a tree and calls an insurance company to cover it, but the salesman informs him that in order to be covered, he needed to have taken out insurance before the crash. Instead, the salesman manages to convince Harry to buy insurance, but then ignores all of Harry's attempts to call him. Dick, meanwhile, is pleasantly surprised when he discovers just how much more advanced his rental car is than the old Rambler, and so sells the latter for scrap; however, the Solomons soon begin to miss it.
Mary is tired of spending all of her time with Dick's family and so suggests that the pair befriend another couple - her tennis partner Gwen and her husband Larry. Dick is apprehensive but quickly warms to the pair; however, they soon start brushing he and Mary off, so Dick finds them at the tennis club, where they tell him that it's because they find Mary to be tedious and self-absorbed. Meanwhile, Sally, Harry and Tommy are forced to use the laundromat when their washing machine breaks down, and immediately fall in love with the place, even setting up a laundromat court, in which Sally, imitating several of the phrases and mannerisms of Judge Judy, settles squabbles over people's washing.
Valentines Day is approaching and Tommy hopes to get a hotel room and lose his virginity to Alissa, however, he is nervous when he discovers that she is sexually experienced and so loses his virginity to Mary's niece Tiffany (Lindsey McKeon) first. Meanwhile, Dick discovers that Mary is seeing a therapist and, paranoid, he starts seeing her too, in order to find out what Mary has been saying about him. Paranoia fills Sally also, when Don gives her a gift which he teasingly says is from her 'secret admirer', and she mistakenly believes she has a stalker.