The relationship between Dwight and Angela becomes known to the viewers in the Season 2 episode "Email Surveillance". They go to great lengths to avoid making their relationship public, including avoiding each other at group functions and speaking in code around others. Despite their efforts, Pam, Jim, Ryan and later Phyllis independently discover the relationship.
Angela breaks up with Dwight in the Season 4 episode "Dunder Mifflin Infinity" over his decision to euthanize one of her cats. Dwight takes the break-up very hard. Angela immediately begins revenge-dating Andy, a relationship that leads to an engagement, but it is clear that Angela still loves Dwight. The two arrange romantic encounters behind Andy's back, but are discovered by Phyllis. When the affair is exposed, Dwight and Andy engage in a duel at the end of Season 5, but decide that neither of them wants Angela back.
In Season 6, Dwight and Angela enter into a child-bearing contract. Dwight attempts to void the contract in order to date Isabel, but Angela holds him to it. During the resulting legal proceedings, the the two negotiate five additional lovemaking sessions.
In the Season 7 episode "Andy's Play", Angela attempts to win Dwight back, but when Dwight is receptive to the idea of rekindling their romance, Angela changes her mind. A few weeks later, Angela begins a relationship with state senator Robert Lipton and voids the lovemaking contract with Dwight.
Angela's relationship with Senator Lipton leads to marriage and a son Philip. Dwight suspects he is the father of the child, but DNA tests indicate that he is not. Nevertheless, the two rekindle their romance in the Season 9 episode "Moving On". Angela becomes jealous when she realizes that Dwight has begun dating Esther, a woman from a neighboring farm.
Angela learns that Senator Lipton is homosexual, and he divorces her publicly at a press conference at which he reveals his sexual orientation.
In the penultimate episode "A.A.R.M.", Dwight realizes that he loves Angela and proposes to her. She accepts and reveals that the DNA results were faked, and Philip is his son after all. In the "Finale", the two are married following Schrute family tradition.
Dwight and Angela carried on a secret office romance for a long time. The exact time that the relationship began is never specified, but it can be assumed to be in the middle of season 2 ("Email Surveillance"). In the first episode of the show, Dwight is seen singing Little Drummer Boy, Angela's favorite song. They kept their relationship a secret due at least in part to Angela's desire not to be the subject of scrutiny by the rest of the office.
In Email Surveillance, Pam notices that Angela bought two Baby Ruth bars from the vending machine, and with the help of the cameraman, notices that Dwight is eating the second one. Later, at Jim's barbecue, Angela and Dwight can be seen having intercourse at the end of the episode.
In the next episode, Christmas Party, a drunken Kelly Kapoor kisses Dwight in the break room. Angela notices this and feeling threatened, she rages in the parking lot and demolishes a box of ornaments.
In Booze Cruise, to avoid suspicion, Dwight and Angela do not attend the cruise together. But when Dwight is steering the ship alone, Angela comes to try to persuade him to stop steering the ship and bond with her. However, Dwight claims he cannot and Angela walks away, miffed.
In The Injury, Dwight has a concussion, causing him to act foolish to Angela. He approached her in the break room, not taking any caution to look around for people that could see them together, and then lovingly spanks Angela before dashing away. Although she isn't very happy with Dwight, when it is apparent that he is unwell, Angela pressures Michael Scott to take Dwight to the hospital.
ln The Secret, Angela and Dwight have a close shave when they stare longingly into each other's eyes in front of Kevin Malone. However, since Kevin isn't the sharpest tool in the shed, he doesn't put two and two together.
In The Carpet, when Dwight and Michael raid accounting, Angela gives Dwight a cold warning look. Dwight, who totally ransacked Kevin and Oscar Martinez's work, only took one pen out of Angela's pen holder before scampering away with Michael.
In Valentine's Day, Angela gives Dwight a bobblehead resembling himself. Dwight does not have a present prepared for Angela, as he didn't expect her to be interested in Valentine's Day. Running out of time, Dwight asks Pam Beesly for help, and after discussing possible gifts, he settles on giving Angela the key to his home.
In Dwight's Speech, Angela feigns sickness in order to be able to leave early to spectate Dwight's top salesman speech.
In Take Your Daughter to Work Day, Angela seems disappointed in the meager amount of discipline that Dwight exhibits in front of children.
In Michael's Birthday, Dwight and Angela squabble for the ice-cream cake. Eventually, Angela caves in and gives Dwight the cake box, but vows that she won't give him a cookie the next time they meet, no matter how hungry he is.
In Drug Testing, Angela seems smug and impressed by the show of power that Dwight is putting on when he questions Ryan Howard about drugs. When Angela herself is sent into the conference room for drug testing, Dwight says that he knows she is innocent, but he has to look like he's not giving her special treatment. With that, he starts to yell at Angela, who isn't frightened at all.
In Casino Night, Dwight and Angela meet at a table. Dwight rolls an eight, the exact number he was hoping for. Elated and impulsive, Dwight suddenly swoops down and gives Angela a peck on the cheek. Angela is shocked, but then slaps Dwight (though not very hard) before pacing away, smiling to herself.
In Gay Witch Hunt, Dwight is enraged when Oscar shoves Angela in a forceful way. He roars and runs forward, throwing alternating push-kicks, though he is restrained by various office workers before he can harm Oscar.
In The Coup, Angela motivates Dwight to meet with Jan Levinson about taking Michael's job, saying that he would run the office much better than Michael. Dwight does so, but pays dearly when he realizes Jan has informed Michael about Dwight's treachery.
In Initiation, Dwight takes Ryan to a sales training. Kelly, Ryan's girlfriend, chats with Angela about how she hopes Ryan will be okay. Angela assures Kelly that Dwight will protect Ryan, but things escalate quickly once Kelly calls Dwight a "Weirdo" and a "Freak." Angela seems extremely offended and screams at Kelly before storming away.
In A Benihana Christmas, Angela goes to Dwight for assistance when she realizes that The Committee to Plan Parties is making a rival party. Dwight orders the members of The Committee to Plan Parties (Pam Beesly and Karen Filipelli) to stop party-planning, but Jim Halpert steps in and is able to make Dwight's efforts futile.
In Traveling Salesmen, Angela forgets to ship important expense reports to corporate. Dwight lends her a favor and drives all the way to New York to give the expense reports in person, but when Andy Bernard finds this out, he convinces Michael that Dwight might be going behind his back again. Andy succeeds, and Dwight is fired.
In The Return, Angela is able to persuade Michael that firing Dwight was wrong and that Michael should rehire Dwight.
In The Negotiation, Dwight saves Jim from being beaten up by Roy Anderson by peppering Roy with powerful blasts of pepper spray. Angela, turned on by Dwight's heroics, tries to find all of the stories and eyewitness accounts of it. Then, at the end of the day, Dwight meets up with her and they kiss passionately together, although Jim spots it from inside the hallway between the Annex and Bullpen.
In Beach Games, Angela is put into Andy's cohort. She meets with Dwight in the tall dunes and promises that she will try to sabotage Andy's cohort in order for Dwight's to win.
In The Job, Angela is thrilled when she realizes that Dwight is the new manager (this is not entirely true, though). She plans to fire Kelly when Dwight promotes her and supports Dwight's Schrute Buck program.
In Fun Run, Angela asked Dwight to care for her severely ill cat, Sprinkles. Dwight decided that the cat should be euthanized instead, and it died trying to escape from Angela's freezer after Dwight's unsuccessful attempt to mercy-kill it.
In Dunder Mifflin Infinity, Angela asks Dwight to take her out for dinner. Dwight is joyful and scrambles to make reservations. However, once there, Dwight is dismayed when Angela breaks up with him, since she is upset that Dwight was the cause of Sprinkles' demise.
But all throughout the rest of the episode and Launch Party, Dwight doesn't take a hint and keeps trying to seduce Angela, who is increasingly distressed by Dwight's continued flirting. She resorts to being cruel, by constantly and publicly hinting that she would like to have a relationship with another man.
In Money, Dwight starts to feel threatened when Andy is making continued moves to flirt with Angela. Near the end of the episode, his worst fears are confirmed- A final present makes Angela open up to the idea of dating Andy, and she gives him permission to ask her out on a date. Dwight quickly runs for the stairs, where he starts to sob. Luckily for him, Jim consoles him and Dwight is able to return to his desk and make sales calls just a few minutes later.
In the next episode, Local Ad, Andy talks to Dwight about his relationship with Angela (not knowing that they used to date). Dwight seems to be trying to tone Andy out, but then listens intently when Andy reveals that Angela always whispers "Oh, D" every time they kiss. Dwight realizes what this means (Angela's nickname for him was "D"), and his spirits are lifted.
In Dinner Party, Dwight feels jealous when Michael and Jan invite Jim, Pam, Andy, and Angela to their house for a dinner party. Dwight crashes the party with his babysitter, Melvina Whitaker as his date. He constantly tries to flirt with Angela, but each time he tries, Angela shoots his attempts down.
In Weight Loss and Business Ethics, Angela sends a secret signal to Dwight every time she feels burdened by wedding planning. Once that signal was shown, both Dwight and Angela ventured down into a secret chamber in the warehouse where they had sex.
In Crime Aid, Dwight took initiative by giving Angela an ultimatum- She would have to break up with Andy by a certain time, or else he would refuse to have sex with her. However, Angela doesn't respond to the ultimatum. Phyllis, who had been helping Dwight with the ultimatum, motivated him to look for someone else to date, but Dwight stubbornly refused.
But it is clear that the ultimatum didn't affect anything. In Business Trip, when Andy calls Angela late at night, Dwight is heard asking, "Who is that, Monkey?" Which probably means that they were sleeping together while Andy was gone on his trip.
In Moroccan Christmas, Phyllis reveals to the whole office about Dwight and Angela's affair. Dwight doesn't seem at all shameful, while Angela seems like a deer caught in the headlights.
One episode later in The Duel, Andy hears about the affair. He challenges Dwight to a duel, but as they fight, both realize that Angela is an immoral cheater. They both break up with her when they return to the office.
In The Delivery, Dwight feels the urge to have a child and asks Angela if she will participate in a child-bearing contract with him. Angela happily accepts, and the two meet in the warehouse to type out the contract.
But in Happy Hour, Dwight violates the contract by starting to get a bit too cozy with Isabel Poreba. Dwight soon feels that he prefers Isabel to Angela, and reassures Angela that the contract is not needed and that she doesn't have to participate in it. But Angela feels differently, however, and vows to take Dwight to court for the breaking of the contract.
In The Chump, Dwight and Angela decide that instead of spending money on lawyers and court hearings, they would use a mediator. After driving hard bargains, Dwight and Angela decide on five more rounds of intercourse.
In Andy's Play, Angela attempts to seduce Dwight by wearing more attractive clothing. This does the trick, and Dwight seems to be falling for her again.
In WUPHF.com, Dwight and Angela schedule another intercourse meetup, but Angela meets Robert Lipton at the Hay Place. Angela seems attracted to him, and Angela breaks up with Dwight, finding better love with Lipton.
In Jury Duty, Dwight goes to see Philip Lipton, Angela's newborn baby. Then, Dwight slowly starts to wonder if the baby was actually his, as months ago, he had sex with Angela one last time and the baby looked far too old to be born recently. Angela gets very defensive once Dwight suggests this and demands him to leave the birthing ward.
In Free Family Portrait Studio, to further try to get evidence that the child is his, Dwight attempts to get Philip's DNA tested. Angela tries to stop him, but to no avail- Dwight is able to get the DNA to the lab. But although Angela lost the battle, she won the war, since the lab told Dwight that he was not the father.
In Moving On, Dwight asks Angela if she could come to Schrute Farms so she could help him tend to his elderly relative, Aunt Shirley. Angela accepts, and after they finish cleaning Shirley up, Dwight and Angela kiss.
But Angela is dismayed when she realizes that Dwight, after getting rejected by her, has started to date Esther Bruegger. Angela's jealousy shows all from Stairmageddon to A.A.R.M., but at the end of A.A.R.M, Dwight pulls her over onto the side of the road and proposes to her.
In the Finale, Dwight and Angela are married at Schrute Farms.
Status: Married 6 Years. (2020)