Jessica Buchanan and Will Rappaport
First Got Together: 1998
When Will's mom, Lindsay, wed Jess's dad, Clint, the teens bonded. Will continued to be there for Jessica when her then-boyfriend, Cristian, began to spend more time with sultry Roseanne. Will and Jessica's relationship changed for good one night when a distraught Jessica got drunk. She lost her virginity to her stepbrother and became pregnant with his child. Sadly, she lost the baby after Dorian mowed her down with a car. Jessica waffled between Cristian and Will, and eventually moved in with the latter. She broke up with him because of his lying tendencies, and he left town.

Al Holden and Marcie Walsh
First Got Together: 2003
At first, these college students didn't get along. Needless to say, Al was less than pleased to have Marcie tutor him. Gradually, a friendship blossomed. Marcie assisted him with his grades and helped him overcome a drug addiction. Meanwhile, he stood by her as she battled with other students over the war, endured vicious hazing from a sorority and was thrown into a Dumpster by her enemies. Eventually, Al and Marcie made love, but she unknowingly passed on a virus she had contracted while in the Dumpster. Sadly, Al didn't make it, but his soul lives on in Marcie's new boyfriend, Michael.

River Carpenter and Adriana Colon
First Got Together: 2003
When Cassie and Andrew's teenage son returned to town, he immediately fell for Carlotta's goddaughter, Adriana. Carlotta was against them being together, so most of their romance consisted of sneaking around. Eventually, Dorian revealed that she was actually Adriana's mother ... which made Adriana River's aunt via adoption, but this didn't seem to bother them. River was much more concerned about sleeping with his girlfriend. Adriana finally lost her virginity to him, but broke things off when she caught him with sexy Shannon McBain. He then went to Juilliard. Adriana had a pregnancy scare, but was thankfully not carrying her, uh, grandnephew.

Starr Manning and Travis O'Connell, 2004
Her daddy was once the main man in her life, but this changed when a distraught Starr ran away to New York City to escape her fighting parents. While there, she met up with an Internet buddy, Travis, and in typical 13-year-old fashion, the youngsters immediately fell in love — and Starr experienced her first kiss. The duo intended to run away to California, but their plans were thwarted when Starr was kidnapped. After Travis helped Blair and Todd find their daughter, they reluctantly agreed to let Travis and Starr date. The pair enjoyed a summer together, but Travis had to return to New York for school.