Later seasons
At the start of the third season, Joe began dating a voluptuous beauty named Sam (Mary Ann Pascal), a very materialistic real estate agent who was not only content with the physical aspect of their relationship, but also out to reap the benefits of an ex-pro athlete's bank account. During their mating dance, Sam became another regular patron at The Point After, where at times she found herself in competition with Kelly over practically everything. Penny, who had rapidly matured from a gentle, innocent high school senior to a wild, vivacious party girl with a punk hairdo, began working as a dancer at Girls, Girls, Girls & Beer, a local dance hall, during her sophomore year in college. Everyone else on the scene had mates that came and went, and Joe was no exception with Sam, as they were on-again, off-again for a while; while Sam chose not to play the field, Joe dated others. In the fourth-season premiere, perky, cultured Ann Marie Wagner (guest star Judith-Marie Bergan) showed up, as a girlfriend of Joe's who had been with him for six months. Joe and Annie decided to get married during the course of the episode, but after much meddling from a jealous Sam, and a discouraging ceremony speech from Donald (who presided over the restaurant ceremony), the two called it off. A few episodes later, Joe went into overdrive dating both Annie and Sam, but felt guilty; when he went to break the news to Annie that he had been playing her, she revealed that she had been cheating too, so the two parted ways mutually, leaving Sam, who encouraged an open relationship, as Joe's only romantic focus.
In time, Joe and Sam discovered that they had a whole lot more in common beyond money and status, and love blossomed. Kelly and Sam even learned to put their feuding aside, forming sort of a "girls' club" together with Penny and Donald. Meanwhile, Cliff, who graduated from college early in the fourth season, was on the verge on launching his journalism career with a local newspaper when he had an epiphany-–that he suddenly had the affinity for cooking—and announced to everyone that he was enrolling in culinary school. Joe, Lou, and especially Donald tried to save him for turning down the offer to work at the paper, but in the end, decided to throw caution to the wind after tasting Cliff's impressive tomato sauce. Later that year, after dating many young men on the fast track, aspiring yuppie Penny fell for none other than Jim Grant (Tommy Hinkley), a construction worker from Lou's company. Jim was actually from a very wealthy family, but loved the laborer's life better, resulting in his turning down the opportunity to helm his family's million-dollar enterprise in order to be truly happy. Their romance lasted a single season. It was also at this time that the youngest of Lou's kids, athletic teenage prodigy Louella (Yeardley Smith), became a regular.
The fourth-season finale saw The Point After get upgraded to a three-star establishment by a local Philadelphia food publication, and Joe quickly received an offer by another top restaurateur for a huge buyout of his place. During the celebration of the three-star news at Donald's, everyone was shocked at the offer given to Joe, and Kelly expressed her worry over losing her job. After a series of flashbacks chronicling memorable moments the cast had at The Point After, Joe ripped up the papers granting its sale, and it was assumed as the episode came to an end that the gang would remain intact. However, as the fifth season began in June 1988, Kelly was no longer around (Robin Riker-Hasley had left the series). At this time, Sam, whom Joe had still been going steady with, revealed she was pregnant. Joe didn't take the news too well at first, since new fatherhood wasn't exactly in his game plan. Sam was dead set against abortion, and ended up giving Joe an ultimatum — either he opened up his mind to having a new family, or she left him to raise the child alone. Joe chose to stand by Sam, and the two rushed off to Las Vegas to tie the knot. Through the next few months he had many adjustments to make, but when their daughter, whom they named Caroline, was born in the December 2, 1988 episode, Joe was more than ready to embrace her. Lou, Cliff and Penny all shared the designation of being Caroline's guardian, in case anything ever happened to her parents. Baby Caroline (who was named after executive producer Gary Nardino's daughter) was played in her birth episode by boy and girl twins Charles and Cathryn Hacker, but for the remainder of the series, was played by Cathryn alone.
As Joe and Sam were busy adjusting to married life, as well as preparing to bring in the newest addition to the Waters family, Cliff found himself getting promoted to manager of The Point After while continuing in culinary school. On the side, he was gradually building his own catering business from scratch, at times joining his services in with the restaurant's catering in order to turn over larger profits. Penny found a new love interest in Mike Chandler (Timothy Williams), a suitor that Joe had an extremely hard time having around. Mike happened to be the lawyer hired by Penny's mother, Joe's ex-wife Janey (who was played in a 1985 guest appearance by Rebecca Balding, Walden's former Lou Grant co-star) to retrieve part of Joe's pro football salary that she had yet to receive as a part of her divorce settlement with him. During their legal dealings, Penny moved out of Janey's house when her mother remarried on a whim, and got her own studio apartment. She graduated from college the following spring, and was hired as a junior writer for a big-time advertising firm.
Other developments included Donald's close brush with a career in Hollywood, when he was hired to meet with a veteran movie actress in hopes of writing her biography. After getting lost in all of Tinseltown's glitz and glamour, Donald decided on his own will that Philly was where he truly belonged, and hired a "stringer" writer to collaborate on the biography project so he could return home. In November 1988, Lou was promoted to project designer in the offices of the large corporation that now owned Santini Construction. He was bribed into taking the promotion to keep quiet about an increase in accidents happening down at the job sites, as a result of inferior conditions and materials the new company provided. Upon finding this out, Lou was faced with a moral dilemma, and ended up quitting after 28 years on the job. He worked many odd jobs to compensate for his loss of income, before Donald proposed a business deal in which he found homeowners who needed private renovating done by a craftsman of Lou's expertise. A local mansion renovation job put Lou on the map, allowing him to buy out Donald's share in the partnership so he could become a stand-alone private contractor. Also, after his own steady succession of casual intimate encounters and regular boyfriends, Cliff's valiant search for Mr. Right continued, with a lot of help and advice from his family and friends.