When Chuck learned he was dying, he asked Bob to take care of his family. Bob kept his word and ended up falling in love. Though Jennifer's daughter, Barbara, liked the Hughes family, Rick, who idolized his father, deeply resented Bob and vehemently opposed their relationship, going as far as to tell his mother that Lisa (who was now dating Bob's brother, Don) was pregnant with Bob's child. Jennifer saw right through the lie and married him. Unfortunately, Rick's poor performance at Memorial put a strain on their marriage because Jennifer continually accused Bob of being too hard on her son, who was an aspiring doctor. However, Bob refused to condone Rick's shoddy work, which included shamelessly stealing patients from Bob and David and making careless near-fatal diagnosis. With Rick a constant source of strife in the marriage, Bob and Jennifer's started coming apart. Finally, at a convention in Florida, Bob was pleasantly surprised to see Jennifer's sister, Kim Sullivan Reynolds. A singer, the widowed Kim was performing in Florida and she and Bob became reacquainted and had a fling. Afterwards, Kim, smitten with Bob, followed him back to Oakdale and observed for herself the deteriorating state of the marriage. Then came a shocking twist—both Jennifer and Kim ended up pregnant. Knowing there was a baby on the way changed everything and Kim decided to cover up the fact that she was pregnant with Bob's child - keeping the secret even from Bob himself. Although Kim had resolved to raise the child on her own, she quickly fell prey to Bob's rival, Dr. John Dixon, and fell for his arguments that she marry him to give the child a name. Later, one night, Bob and Jennifer fought and Bob ran out of his house and was hit by a car, in a delirious state, he blurted out to Jennifer that Kim was pregnant with his baby. Though shocked, Jennifer placed the brunt of the blame on herself and resolved to be a more understanding wife. Late that year, as Jennifer gave birth to their daughter, Frannie, while Kim was told that she had suffered a miscarriage. Kim stayed in her loveless marriage to John while Bob and Jennifer resolved to patch their marriage back together. Though things got easier when Rick left town, tragically, Jennifer would lose her life in a car accident, leaving Bob to raise Frannie alone. Not long after, Sandy returned to town, running from her abusive husband, Norman Garrison. Soon, Norman followed demanding that she return to him.