The 62-year-old media mogul and 64-year-old businessman were all smiles in a snapshot Winfrey shared on Instagram captioned, "Stepping out with my Valentine of almost 30 yrs!"
Winfrey and Graham took the photo at Liberty Ross and Jimmy Iovine's wedding Sunday. The 37-year-old model and 62-year-old Interscope Records co-founder married in Malibu, Calif., and requested female guests wear red.
The post showed off Winfrey's slimmed-down figure after her nearly 30-pound weight loss. The television personality became a spokesperson for Weight Watchers last year and revealed she's lost 26 pounds in a promotional video in January.
Winfrey and Graham have been together since 1986, but largely keep their relationship out of the spotlight. The couple were engaged in 1992 but never wed, and Winfrey later told Access Hollywood she doesn't believe she'll ever marry.
"I thought about it again at Tina Turner's wedding," she said in 2013. "Because Tina was like, 'Oprah, you need to do this. You need to do it.' And I was just thinking, 'Well, okay, would things really be different?'And no, I don't think so."
"If you ever interviewed [Stedman], he would tell you that had we married, we would not be together today," she shared. "Because he's a traditional man and this is a very untraditional relationship."
Graham attended an Oprah Winfrey Show taping just three times during the series' 25-season run. Winfrey has further developed her Oprah Winfrey Network since the talk show came to an end, and presently hosts Where Are They Now? on the OWN channel.