Oscar-Robert Lipton Relationship

Oscar Martinez and Senator Robert Lipton had an affair while the senator was still married to Angela. The exact moment that their relationship began, is unknown, but it started between Free Family Portrait Studio and New Guys. After the Senator realizes that his homosexuality would be revealed anyway when the documentary releases, he comes out in Stairmageddon as gay and divorces Angela and also breaks up with Oscar.

Season 8
Oscar starts to warn the office that Senator Lipton could be gay, but they pooh-pooh his accusations. Oscar takes it one step further in Fundraiser, where he claimed that the Senator gave him his number to call and touched him. Jim doubts this and proves that the Senator treats everyone the same by doing the same thing. But this is proved wrong in Free Family Portrait Studio, where the Senator reminds Oscar to call again, very covertly.

Season 9
Their relationship starts to become very visible in New Guys, when Oscar offers to take on Angela's former cat Comstock, who had to be ousted since Angela's son, Phillip was allergic. When Oscar hears that Comstock is Robert's favorite, he snaps him up and is shown revealing that he took in Comstock in the stairwell to Robert over phone.

In Here Comes Treble, Oscar and Robert are shown kissing in a hidey-hole in the parking lot before Robert leaves. Oscar sees him off and then is alarmed when he spots the documentary cameras pointing right at him.

Oscar pulls the documentary crews aside in The Boat and talks about his relationship with Robert, but Kevin had been eavesdropping and now knows the secret. This makes things even harder, and Kevin comes very, very close to revealing the affair to Angela, and when Robert arrives in the office, it makes things even harder. However, Kevin forgets all about the affair and Angela has no clue.

In The Whale, Angela starts to realize that Robert and Oscar are having an affair after they scout him out at a yoga gym. She is irate and asks Dwight for assistance in The Target.

Dwight's helper, Trevor tries to break Oscar's knees, but fails. After that, the relationship is tranquil, until the Senator reveals that he is gay in a press conference and kisses Wesley Silver, who he had also been dating. He ends his relationship with Oscar and Angela, never to be seen again.

Status: Broken-Up