The Office: 10 Biggest Milestones In Dwight and Angela's Relationship

Dwight and Angela's relationship was one of the ongoing romances in The Office. Most fans swoon over Jim and Pam's bond, but Dwight and Angela's deserved respect aspect as well. It's not known when the couple began dating officially, but they wanted to keep their union a secret from Dunder Mifflin.

RELATED: Dwight & Angela's Relationship Timeline In The Office, Season By Season

As time wore on, Angela and Dwight broke up, made up, and experienced everything in between. Regardless of lovers, engagements, or marriages, these two couldn't stay away from each other. Each milestone moved them further in their relationship until they eventually said "I do" in the series finale.

In season 2, viewers became aware that Dwight and Angela were in some sort of secret relationship. The severity of their relationship became well-known in "Valentine's Day" when Angela got Dwight a bobblehead version of himself for his desk. Dwight soon realized now that he was in a relationship he had to give Angela a gift as well.

With a little help from his underrated Office best friend Pam, Dwight gave Angela a monumental gift for their relationship: a key to his home. From there on, they became more serious.

One of Dwight's best quirks or attributes is that he would do anything for Dunder Mifflin. As odd as he can be at times, he's a hard worker. Likewise, he's also a dedicated partner.

RELATED: Each Main Character's Best & Worst Quirk In The Office

When Angela messed up at work and forgot to send in Dunder Mifflin's expense reports, Dwight helped her out and hand-delivered the reports to corporate. Dwight driving more than two hours to help Angela in her time of need was a milestone in their relationship. Even more, Dwight was fired for covering for Angela and refused to admit their relationship to help his case. In those moments, Angela realized what a pillar of strength Dwight was.

Angela and Dwight's first breakup occurred after "Fun Run" when Angela found out Dwight mercy-killed her cat, Sprinkles. To get Dwight off her back, Angela started dating Andy as a means of hurting him and moving on. However, she wasn't attracted to Andy. Sooner or later, she started sleeping with Dwight again.

Eventually finding out, Andy had a duel with Dwight to see who was better for Angela. But when Dwight found out that Angela slept with the both of them, he was gutted. At that point on, Dwight was done with Angela and the torment she put him through. They've had breakups before but this one was monumental.

In season 6, both Angela and Dwight were still broken up and not sleeping with each other. It was the longest they had been apart in the series. Eventually, however, Dwight realized he wanted to be a father and who better to have a child with than Angela? Angela agreed to mother his child and a child contract was soon put in place.

RELATED: 10 Things On Dwight And Angela’s Child Contract

Without having a romantic relationship, the two embarked on a contractual agreement to sleep with each other a number of times until a child is conceived. Eventually, Dwight and Angela realized they were in different places in their lives and a child (and a child contract) wasn't working for them, so they ended it abruptly.

Around the time of Angela and Dwight's child contract, Angela met Senator Robert Lipton and fell in love with him. She ended things with Dwight, got married to Robert, and had a baby named Philip. At the time, Dwight didn't seem to care about Angela's new relationship, but when he realized how much her baby resembled him... he became intrigued.

It became clear that Dwight and Angela still messed around early in her and Robert's relationship. This meant that Dwight could potentially be Philip's father. The thought that Dwight fathered a baby, after all, became all-encompassing and he did everything he could to find out if Philip was biologically his.

When Angela found out that her coworker Oscar was sleeping with her husband, she fell apart. She had no idea that her husband was using her as a tool for his political goals. At that moment, the only person Angela relied on was Dwight.

Dwight and Angela proved they were relationship goals without even being in a relationship. He listened to her cry and promised to help her get revenge on both Oscar and Robert. Dwight comforted Angela during this stage and the two restarted their friendship. Her breakup with Robert was a big point in her relationship with Dwight.

In season 9's "Moving On," Dwight's Aunt Shirley stayed with him at Schrute Farms and he needed assistance from a woman to bathe and care for Shirley. The only possible option was Angela. Angela was happy to help Dwight; she was also the only one tough enough to endure Aunt Shirley's aggression.

Angela may have done bad things to Dwight over the years, but they were washed away when he saw her care for his ailing aunt. Dwight grew newfound respect and admiration for Angela as he watched her braid Shirley's hair, bathe her, and care for her. This was a huge turning point in their years-long relationship.

Despite the dramatic love triangles, baby, and deception, Angela and Dwight couldn't hide their feelings for each other. Regardless of who they ended up with, their new partner would never compare.

Eventually, Dwight had enough of the games and told Angela how much he loved her and that he didn't care if Philip wasn't his son — he wanted to marry her. Angela was happily surprised and accepted his proposal. She also told him the good news: Dwight was, in fact, Philip's father. The series ended with their wedding, tying up the biggest milestone in their union.

NEXT: 10 Most Dramatic (And Funniest) Love Triangles On The Office



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