Bonnie Winterbottom, How To Get Away With Murder

Bonnie Winterbottom (Liza Weil)

Bonnie Winterbottom is one of the main characters of How to Get Away with Murder, and lead Annalise’s dedicated assistant. She is the only person out of Annalise’s Keating 4 groups that remained with her over the years.

Bonnie’s father sexually abused her as a child and the case was presumably taken to court since Annalise had access to related files.

Bonnie only had relationships with men on the show. In season 1, she hooked up with an unnamed man at a bar and went back to his hotel room. It was also implied throughout the season (and Annalise suspected) that Bonnie was secretly in love with Sam Keating, Annalise’s husband, and in an attempt to manipulate her, Sam kissed her, and Annalise fired her as a result.

Bonnie then slept with and started dating Asher Millstone, one of Annalise’s interns, but broke up with him first when she suspected Asher of cheating and then permanently when she discovered his role in a gang-rape coverup.

In season 3, episode 5 Bonnie traveled to Coalport to take care of her father’s funeral arrangements and to meet with Frank Delfino at a motel, trying to convince him to come back to Philadelphia – and telling him that he and Annalise just needed to forgive each other for everything. Later, Bonnie was in bed while Frank slept on the floor. He suggested they run away together, to a small town somewhere where they could live normal lives and have a family (“We’d have cute babies, no?”) but quickly added he was only teasing. After Frank had a bad dream, Bonnie tried to relax him which lead to them kissing and having sex. It was unclear whether it was the first time or whether it had happened before.

Relationship with Annalise

Throughout the show, Bonnie’s relationship with Annalise toes the line between mentor-mentee and single white female obsession on Bonnie’s side. Throughout the series, Annalise emotionally abuses and takes advantage of Bonnie and they share a co-dependent bond.

Bonnie is also responsible for the murder of Rebecca Sutter, whom she strangled with a plastic bag, because she believed that Rebecca had killed Lila and wanted to protect Annalise.

Actress Liza Weil also called the relationship maternal: “There’s a real need to connect and feel seen, so I think that can be confusing to everyone. But I think there’s also a maternal thing that they have with each other. They take turns taking care of each other in a very pure way. I don’t know if it’s going to be as sexualized as people might initially think.”

In episode 3×06 Annalise got into an argument with Bonnie, after she found out Bonnie met up with Frank. While trying to convince her she hadn’t betrayed her, Bonnie told Annalise she was willing to put up with whatever treatment she wanted to dish out, and also told her that she loved her.

In episode 3×09, after Annalise was charged with arson and first-degree murder and she was convinced she’s be going to jail, she went to see Bonnie, who instead of joining her drinking, fed her soup and coffee, tucked her into bed and kissed her. Both executive producer Pete Nowalk and Viola Davis called it a moment of drunkenness.

Female love interests:

• Annalise Keating (Viola Davis, bisexual, regular)

Relationship story arc with a woman: Questionable

Male love interests:

• Unnamed man (uncredited)
• Sam Keating 💀 (Tom Verica, recurring 17 episodes, kissed)
• Asher Millstone (Matt McGorry, regular)
• Frank Delfino (Charlie Weber, regular)

Relationship story arc with a man: Yes

Filter Relationship Arc:

• Male (Regular)

Storyline during sweeps? No

[1] A relationship story arc is defined as explicit, developed on screen, and lasting more than 3 episodes. It is listed as questionable or subtext if romance is only implied, mentioned instead of shown on screen, part of a dream sequence, or otherwise not explicit for the viewer.
[2] Sweeps episodes air in February, May, July and November, the periods when advertising rates are set. A character is marked as "sweeps" when there is a very limited number of episodes that address their sexuality, all air during sweeps period, and the storyline is otherwise ignore/dropped.