Oliver Jones is the cousin of Whipple Jones III, and the brother of Agnes Jones (AKA Sandy Sommers). Oliver had been a source of strength when Agnes was raped years ago, and was in Los Angeles reconnecting with Agnes. While working as a DJ at the Insomnia Cafe, Oliver, on separate occasions, met Hope Logan and Steffy Forrester. Oliver and Hope hit it off, and began dating. But Steffy had her eye on Oliver as well, in part to harass Hope, her adversary. Steffy teased Oliver in sexy lingerie, and they kissed, but Oliver had fallen in love with Hope.
One night, Oliver accidentally videotaped Bridget Forrester and Owen Knight cheating on their respective spouses. Steffy was on an anti-Logan crusade, and, since Bridget was Brooke Logan's daughter, Steffy tried to sweet-talk Oliver into giving her the video so she could hurt Brooke. Oliver talked Steffy out of the scheme and uncovered Steffy's vulnerable side, but stayed true to Hope.
Hope was having a graduation party, and Oliver used his connections to have Daddy Yankee perform at the bash, where the guests wore identical costumes and masks. Hope had told Oliver she would let him know when she was ready to let him take her virginity, so, at the party, Oliver heard Hope whisper "I'm ready," and Oliver made love to Hope on the terrace. But Oliver was horrified when he discovered he had made love to Hope's mother, Brooke, and that Brooke thought she was making love to her husband, Ridge Forrester.
Steffy pounced when she found out: Hope had to leave for college, Brooke had to leave Forrester, and Oliver had to date Steffy, otherwise Steffy would expose Brooke and Oliver. Brooke confessed to Ridge, who forced Steffy, his daughter, to produce a tribute video to Brooke as punishment. Spencer Publications got hold of the video and added a recording of Steffy talking about the "mask boink." Soon the truth was made known to the world, and Oliver was humiliated. Hope couldn't get the image of Oliver and her mother out of her head, and dumped Oliver. Ridge let Oliver keep his newfound job at Forrester, but punched Oliver to even the score.
Amber Moore, who was working at rival fashion house Jackie M, cozied up to a vulnerable Oliver, who was pining for Hope. Oliver was using his iPad to produce a video featuring Forrester designs. Amber figured out Oliver's password ("Hope") and gave the designs to Jackie M. Oliver was still allowed to keep his job, but Amber was fired and needed a place to stay, so a forgiving Oliver put Amber up. Amber and Oliver got drunk one night and had sex, and soon Amber discovered she was pregnant. But Amber was determined to name the rich Liam Cooper, who she had also slept with, as the father. As Hope was now seeing Liam, Oliver worked with Amber to break them up. In addition, Liam's father, the powerful Bill Spencer, Jr., put pressure on Oliver to lure Hope away from Liam.
Hope and Liam went through a dizzying array of breakups and makeups, trying to decide between their love and what was best for the baby. Oliver made sure to be there for Hope, and even asked Hope to marry him. But when Amber gave birth to an African-American baby (Marcus Walton Forrester had been Amber's "friend with benefits"), Liam raced to the Big Bear cabin and exposed Oliver's part in Amber's scheme.
Afterwards, Oliver was only occasionally seen doing photo shoots or working Forrester events. Much later, listening to Hope lament repeatedly losing Liam to Steffy, Oliver admitted he still had feelings for Hope and showed her an ankle tattoo he'd gotten of the Chinese symbol necklace he once gave her (which had figured into his “mistaken identity sex” with Brooke). Oliver continued to support Hope as Liam prepared to marry Steffy a second time.
Oliver moved in to a beach house with Steffy's brother, Thomas Forrester, and together they tried to cheer up the sullen Hope. Asked to take part in a fundraising fashion show, Oliver modeled sleepwear with Thomas and other male executives at Forrester to benefit the Caroline Spencer Cancer Foundation. Later, Oliver was hired to do a photo shoot at Jabot Cosmetics in Genoa City, Wisconsin, where he captured images of Summer Newman and caught up with old friend Tyler Michaelson.