Bobby was conceived by Sybil Thorne and Cliff Warner shortly after Palmer engineered a breakup of Cliff and his daughter, Nina. Sybil used Bobby to keep Cliff close to her after his birth, even though Cliff was married to Nina at the time. After Sybil was murdered, Cliff and Nina raised Bobby and Nina adopted him when he was still a baby. Bobby had a happy childhood, despite his parents divorcing and remarrying three times.

After many years away from Pine Valley, Bobby returned in the fall of 1995 to live with Palmer and Opal because Nina and Cliff could no longer handle this bold, young rebel. Bobby enrolled in Pine Valley High School where he romanced Anita and tried to seduce her. Kelsey Jefferson's arrival, pregnant with his child, forced Bobby to leave Anita alone. Kelsey constantly threatened to tell Anita who the baby's real father was, even after she gave him up for adoption to Anita's sister Maria and her husband Edmund Grey.

Bobby came to really love Anita, but the truth about Sam's parentage split them up. Bobby married Kelsey after she took Sam back with the agreement that she would give the baby back to Edmund and Maria in trade for one half of his trust fund, which he thought he would receive upon marrying. After Sam was safely and legally adopted by the Grey's, Palmer convinced Kelsey to annul her marriage to Bobby. Bobby's devotion to Sam and his willingness to return Sam to the Greys, even though he truly loved him, convinced Mr. and Mrs. Santos that he was worthy of dating their daughter, Anita. On New Year's Eve (1997) Bobby and Anita announced their engagement and their plans to marry after graduation from high school and before entering college.

Shortly after their high school graduation, Bobby and Anita left Pine Valley and headed to The Windy City. There they will attend college and begin a life of their own---together.

Anita returned to Pine Valley in the winter of 2004 to help Maria and Edmund, following Edmund's shooting and subsequent paralysis. Anita brushed off advice from her mother, Isabella, to return to Chicago and be with her husband. When Bobby tracked his wife down in March 2004, it was then revealed why Anita had left her husband: Bobby had had an affair with a co-worker and the affair devastated their marriage. Bobby tried desperately to repair his marriage, but he kept causing himself more trouble by lying to his wife about business ventures and his role in trying to seduce Greenlee Smythe Lavery into bed. Eventually, a furious Bobby gave his wife what he thought she wanted: a divorce. After his dealings landed him in the hospital, Bobby fled town, location unknown. He has no idea that Sam knows he is his son.