At age 17, she reconnected with then little-known actor Rob Lowe, also 17. They had met briefly when they were about 14. In 1981, Gilbert, in her convertible, saw Lowe stopped next to her at a red light. Gilbert dated Lowe on and off for six years. During this time, both had affairs with other famous people. She also dated Tom Cruise, John Cusack, Scott Baio, and Billy Idol. After Lowe's failed romance with Princess Stéphanie of Monaco, he suddenly proposed to Gilbert. While making wedding plans, Gilbert found out she was pregnant. Upon being informed of the pregnancy, Lowe ended their relationship. Gilbert miscarried days later.