- "We're all bad people. That's the only thing we have in common."
Bonnie Winterbottom is one of the main characters of How to Get Away with Murder. She appears sweet and kind, the perfect counterpart to Annalise, but she will show her claws when you least expect it. As Annalise's dedicated associate, Bonnie works around the clock to do all the behind-the-scenes casework, as well as help guide the students. Though she may reprimand Frank about his questionable decisions when it comes to his personal life, she is his biggest ally and protector. Besides, Frank knows that Bonnie has secrets too.
Bonnie's father sexually abused her as a child. The case was presumably taken to court since Annaliese has access to related files. ("Meet Bonnie")
Ten years before Annalise gets shot, Bonnie was one of the Keating 4. She was very shy but also very efficient. She helped Annalise with some of the struggles of her pregnancy ("She Hates Us"), while she was getting therapy from Annaliese's husband, Sam Keating. She is the only one from Annalise's Keating 4 groups that stayed working for her over the years.
Bonnie is too friendly with Sam Keating, Annalise's husband. ("Pilot")
Bonnie Winterbottom escorts Gina Sadowski, a woman charged with the attempted murder on her boss and lover, Arthur Kaufman, into the office of Annalise Keating so she can tell her side of the story to the professors law students so they can come up with a defense, which will help her walk free. After Annalise explains the competition to the students, she tells them they can get help from her associates, Frank and Bonnie. After Frank introduces himself to the class, Bonnie introduces herself, explaining that she'll like the students more if they come to her with answers instead of questions. When the students present their ideas, Bonnie and Frank help Annalise determine who will go through to the next round. After the winners are chosen, the court sessions start. Bonnie sits in the sessions on the defense desk, and she is in charge of most of the evidence and facts for the case. When Connor Walsh presents an illegally obtained email that will help the case, Annalise uses Bonnie to help confirm its legitimacy in court...and it works, impressing Connor. Later that night, Bonnie and Frank stay at Annalise's office while the professor and her selected students attend a formal party with Sam Keating, Annalise's husband. Annalise and Sam return to the office as Bonnie and Frank work. Bonnie, over-friendly, greets Sam and gives jealous looks towards Annalise as she kisses her husband. Later on, Bonnie witnesses Frank flirting with Laurel, so she wants him to stop "screwing the students". The following day, after learning Gina bought aspirin the night before the attempted murder, Annalise is upset with Frank for not getting that bit of information out of the client. They end up winning the trial; however, Nate Lahey is later brought in to testify. Bonnie is then present when Annalise reveals who will come to work at her firm. She gives Frank suspicious looks when it's revealed Laurel is one of them. ("Pilot")
Bonnie talking to a guy at a bar. ("Kill Me, Kill Me, Kill Me")
In a bar, Bonnie is listening to the TV broadcast about Lila. A man is sat next to her. He tells her that the stuff that they are saying about Lila is crazy. Bonnie asks him if he has secrets to hide and the man replies "don't we all?" Later, in a posh hotel, Bonnie is kissing the man who was talking to her at the bar. Bonnie asks him about his job. He tells her that she smells so good and continues to kiss her. After, Bonnie is leaving the hotel in a bit of a rush and looks emotional. She calls Asher and asks him if his party is still happening. He tells her it was kind of a bust and asks her why. She tells him that she could swing by his place for a bit. Back in the car, Laurel suddenly notices Asher crossing the road directly in front of the car. Connor stops the car before he ploughed him over. Asher is surprised that Bonnie would want to spend time with him and stops in the middle of the road blocking Connor's car unknowingly. Bonnie asks him if it is ok with him. He tells her that he will be there in 20 and walks off. Bonnie hangs up the phone and walks out of the hotel. She the goes to Asher's place. Asher casually tidies up while Bonnie looks at something. He asks her if she wants a drink. Bonnie tells him that she thinks that she's had enough and takes off her shoes while sitting on his couch. Asher asks her if she has had a rough night. He offers to talk about it. She tells him no and to sit down while stroking the chair. Asher doesnt want to take advantage of her as he thinks that she if pretty wasted. She tells him that shes a woman and she knows what she wants, even though she might be drunk. So she tells him to get over there. Asher sits down next to her and Bonnie gets on top of him and kisses him. He lifts her up and moves her on the couch. She hits her head on some books. He moves them while she tries to get his pants down. ("Kill Me, Kill Me, Kill Me")
Asher and Bonnie after sex. ("Kill Me, Kill Me, Kill Me")
After Asher and Bonnie have sex, Asher checks his phone and sees pictures of Connor, Wes, Laurel and Michaela at the bonfire. He says that they never even wanted to go. Bonnie says that he can never tell anyone about them. Bonnie tells him that them having sex never happened. Asher agrees and claims to never be 'that guy.' Asher wants it to happen again when Bonnie's phone rings. She answers it and its Annalise crying. She asks Bonnie if she is with Sam and Bonnie says no as she isn't and asks why. Annalise tells her that something terrible has happened. ("Freakin' Whack-a-Mole") She tells her that they fought last night after she left and that the D.A. was going to find out that the baby was his. He thinks he is going to go away for the murder. She says that he isnt answering his phone and she's worried that he might have done something stupid. Bonnie tells her to stay right where she is and that she will be right over. Asher asks who was on the phone. Bonnie tells him that she needs to get to the office. He offers her a ride and breakfast but Bonnie doesn't think that its a good idea. ("Kill Me, Kill Me, Kill Me")
When Asher gets suspicious of everyone's seretiveness and wanted to testify stating that Annaliese had asked her lover Nate to kill her husband Sam, Bonnie goes into detail explaining to him that Sam almost raped her and that is why she had to kill him. Later, Bonnie follows Asher, she discovers that he bought himself time. She reports this to Annalise, and then Asher comes into her car. Asher asks questions about Frank and the murder. Bonnie tells him that Frank helped and that the others do not know about this, so he must keep this a secret. Bonnie als falsely confesses that she used Asher as an alibi for her murdering of Sam. ("Meet Bonnie")
Bonnie was romantically linked with Asher Millstone, one of the Annalise Keating's interns. They had sex for the first time the night Sam was killed, then again after Bonnie won her first case in court. They broke up when Bonnie suspected Asher of seeing another woman, not knowing he was behaving strangely because he was being blackmailed by Emily Sinclair. Their relationship ended permanantly when Bonnie discovered Asher's role in a gang-rape coverup and learned Annalise had revealed Bonnie's past trauma to him