Photo of Street Sense vendor Roberta Bear in her sales vest.
Peter Suwondo

Roberta Bear’s voice sounds like it could belong to the Fairy Godmother in the original production of Cinderella. But up until two years ago, when she started working with Street Sense, not many people had the privilege of hearing it.

“I’m a very sensitive person. I’m very shy, so I’m trying to get out of myself and meet people and get the word [about homelessness] out,” she says, when asked about her goals with Street Sense.

Bear graduated from Drake University in Des Moines, Iowa, with a degree in human services. She has career experience working with special needs adults and children. “I’m a caretaker,” she summarizes, smiling. Despite being 57, this is still the profession to which she enthusiastically hopes to return.

On the street, Bear’s sweet disposition has both advantages and disadvantages. She left her hometown, Chicago, in 1984, to “take a vacation” to her uncle’s house after battling with a love-induced drug addiction, but her passion for taking care of others led her astray yet again. She wrestled with addiction and domestic abuse, which followed her for 11 years, until finding help at the Oxford House and The House of Ruth, both in DC.

She says of the struggle, “I never went back [to Chicago], and my addiction followed me. I was just clean [not recovered], but of course when I found someone who was also an addict …” At this she embarrassedly blushes and abandons the sentence. “It’s always men! It’s always men who I become attracted to and want to change, and then I get started. I call it my man-picker. My man-picker is broken!”

In this statement, Bear unknowingly connects with billions of both unsheltered and sheltered women around the world.

Now in transitional housing and drug-free, Bear has a perspective that is jaded, yet hopeful. She has returned to her faith and has confidence that “God is changing and protecting” her. Bear’s favorite part about working with the newspaper is “getting to know the customers,” and she’s always amazed at the amount of love and concern some of her regulars show her. She is grateful for the men and women who encourage her to not “stay out here [in the cold] too long” and who care for her like family.

If she could tell the public about any one thing, it would be the ease into which a person can fall into a life of poverty. “When I came from Chicago, I knew nothing about homelessness,” Bear says. “I had a sheltered life.” At this comment she pauses, as if to contemplate whether by “sheltered” she means “naive” or “housed.” Perhaps it means, as it does for so many people in the city, both.

“Homelessness can happen to anybody. … People need to know what homelessness is all about. We aren’t bums. I wasn’t born to be homeless. People need to understand that a lot of us are trying to help ourselves.”

Bear uses the money she makes selling the paper for medicine and food. She enjoys watching action movies, eating Chinese food, and spending time with her friends and with “positive people,” especially the ones who have their own inspirational stories to share, which encourage and motivate her.

This month she will travel to Chicago to reunite with her family after many years. She is beyond excited for her trip.

Bear sells Street Sense in the Van Ness neighborhood and at the Sunday Dupont Circle Farmers’ Market. When you see her, feel free to give her a big ol’ hug; it might just make her day.