Deborah Gregory, 43, had never been what she calls a “program person” — someone who sticks with addiction treatment. But she found out she was pregnant a few months ago, and she didn’t want her baby taken away.
So she agreed to try Women’s Hope, a residential treatment program that blends into a quiet row of Edwardian-esuqe houses in San Francisco’s Mission District.
“It’s the first time I’ve completed anything in my life,” said Gregory, who recently graduated after a 90-day stay.
Gregory returned to the house last week for a special occasion: a makeup tutorial featuring two political heavy-hitters. The teacher was Honey Mahogany, an activist and politician who once competed on RuPaul’s Drag Race. Her canvas was retired San Francisco Superior Court Judge Ellen Chaitin.
Chaitin and Women’s Hope go way back. Chaitin presided over San Francisco’s juvenile dependency court, which handles cases of child abuse or neglect. She said she referred dozens of mothers with substance abuse issues to the program.
“The moms were bedraggled and beaten, recovering from labor and childbirth, postpartum issues and detoxing,” Chaitin said. To avoid their newborns being put into foster care, they elected to go to Women’s Hope, where they could live together. “What I witnessed during their regular court appearances was transformative,” Chaitin said.
The atmosphere at Women’ s Hope is closer to a co-op than a clinic. Children run down the hallways under the watchful eye of staff who wear many hats: nanny, substance-abuse counselor, therapist. Mothers in the program typically keep a tight schedule of room checks, parenting classes, and counseling sessions.
But on this day the transformation talk was light-hearted. For a few hours, the women gathered in a room that smelled of lotion and fresh roses to learn how to do something just for themselves. The theme of Mahogany’s tutorial was “You deserve to bloom.”
At the news that a judge was among them, the dozen or so former and current residents tittered. One, Alexis Hale, looked around. “Where’s the judge at?” she asked.
“Retired,” Chaitin clarified. “Don’t get scared.”
As Mahogany dabbed primer on Chaitin’s cheeks, women called out makeup techniques they were interested in.
Hale wanted to learn how to contour her nose “like a Snapchat filter.”
Mahogany agreed to share some tips, but, she added, looking like a filter should never be an expectation. “Make-up is personal,” Mahogany said. Chaitin “may not be looking for an airbrushed look.”
Chaitin was not, in fact, going for an airbrushed look. She was a ’60s kid, she said. Doing her make-up or plucking a hair on her body was not a concern. But she did warn Mahogany that she had a lot of freckles.
“You looked beautiful before she started,” one woman said to Chaiitin. “She doesn’t need much at all,” another chimed in. “I love her,” Hale decided.
“I deserve it,” Chaitin mumbled as Mahogany powdered her face.
This comfort is hard-won, staff said. Mothers often arrive at Women’s Hope scared to even ask where the coffee is.
Many are referred through Family Treatment Court, a program that runs parallel to juvenile dependency court. Parents who opt in receive addiction treatment, temporary housing, and parenting classes for one to two years at places like Women’s Hope.
Several alternative San Francisco courts offer defendants, like young adults, veterans, or people with mental health disorders, a chance to avoid a prison sentence if they complete a treatment program.
But Family Treatment Court is unique among them. Its clients don’t risk their cases getting sent back to criminal court. They’re not trying to clear felonies from their records. There is no guarantee that parents who comply will get to keep their kids.
Despite this, Family Treatment Court has among the highest graduation rates of the city’s collaborative courts. Graduates outnumbered those who left the program more than two to one, according to San Francisco Superior Court data from July 2022 to October 2025.
Not everyone at Women’s Hope comes from the court system. Gregory was referred by the hospital. Briana Hightower’s brothers helped her find a place where she could escape from a problematic ex. Paula Alvarado had never touched drugs, but she did have a case with Child Protective Services.
They all had one thing in common: The feeling of home cultivated by staff made them stick with this program, the women agreed.
Program Director Shelly Wynne has complete faith in her clients’ ability to transform. She credits HealthRIGHT 360, the city-contracted nonprofit that operates Women’s Hope, for saving her own life when she was a client.
Wynne’s concern is the lack of resources for women once they graduate. Many transitional programs do not accept mothers with older children, she said. That’s why Women’s Hope makes a point of inviting graduates back for workshops.
Makeup may seem trivial, organizers added. But it’s a reminder to women focused on improving for their children that how they feel about themselves matters, too.
As Gregory departed, her lashes now dark with mascara, Wynne rattled off encouragements in her wake, like a sports coach.
“Keep coming back.”
“It works if you work it.”
“Love you.”