She crossed the street to buy the stranger a cup of coffee. The lunch-cart vendor took her order with a casual "How you doin'?"
"I guess I'm all right," Karen answered, her words cheery but her eyes welling up. "At least, I'm not waking up on the street like that woman over there."
"So why are you crying?" the vendor asked, looking down at her with concern.
Because, Karen explained, that used to be her.
Three years ago, at age 46, Karen Webb was a fixture on Market Street.
She was thin and dirty, with matted blond hair. She pushed around a shopping cart and wore black Harley-Davidson boots. She hid her hair under a bandanna in the summer and a wool cap in the winter.
She would sit on the sidewalk and panhandle with a cup, a sign - "Homeless and hungry" - and her dog, Kenya.
People loved the big pit-bull mix and tossed coins in Karen's cup. They offered to take Kenya home. Not her owner.
With the hindsight of sobriety, she sees that much of the mess of the last five years was the result of her choices.
Karen Webb grew up in a middle-class household in Hatboro, Montgomery County. Her father was an elementary school principal, her mother a piano tutor. The oldest child, she had a brother and two sisters.
When she was 12, as the family was returning from a Fourth of July celebration, her 8-year-old sister was killed by a drunken driver, an event that scarred the family, but particularly Karen. "That threw her," said her mother, Ricki.
As she got older, Karen held a string of jobs, from working for a veterinarian to washing trucks, but nothing that lasted long.
At 32, she was diagnosed as bipolar, and began receiving government benefits of $674 a month.
Nowhere to go
Her world started to unravel in December 2006, when she stormed out on her father after a disagreement.
She grabbed her things and threw them in her Blazer. She slept in her truck for months. Living off her benefits, she was content - until Philadelphia police towed the Blazer from a meter on Delaware Avenue.
It was spring 2007. Karen didn't have the money to pay off her parking tickets, or a fall-back place to stay. Her drug habit and mood swings had left little room for family or friends.
She had nowhere to go but the streets.
"I'd never slept outside," Karen recalled. She put her only belongings - six blankets - in an old baby stroller picked from the trash. "I was by myself and thinking, 'Where am I going to lay my head?' It was getting dark, dark, dark."
As office workers streamed from the Federal Building at Sixth and Market Streets, she thought about curling up next to a wall there. But she nixed that idea. Too exposed.
Wandering the streets east of City Hall, she settled on a spot under a pine tree near the Vine Street Expressway.
She slept little. "I was terrified," she said, "that someone might come up to me and stab me, or rape me, or beat me over the head."
Karen got an education on the streets. She learned to pick out buildings with overhangs - cover on rainy or snowy nights. She figured out how to pee in a cup. She also knew whom among her homeless friends she could trust to watch her stuff when she ducked into a building to use a public restroom.
She had favorite places to sleep: a dead-end alley behind a Burger King at Eighth and Market; next to the front door of the Independence Branch of the Free Library on Seventh Street.
Many nights, she set down her blankets next to a parking garage on a walkway near the former Rohm & Haas headquarters at Sixth and Market. She would awaken with the tolling of the church bells in Society Hill.
"I would count the bells," she recalled. "If I would hear five bells, I knew I had made it to another day."
Too many rules
Going into a shelter was not an option as far as Karen was concerned. Too many people, too many rules. "I'm not good with authority," she confessed.
Plus, shelters don't allow pets, and Karen was not about to abandon her dogs for a cot.
There were always dogs. When she first hit the streets in the spring of 2007, she had a Doberman pinscher and a shepherd mix. One died, one disappeared. They were followed by Kenya, the pit-bull mix that she got from someone she met at a soup kitchen in Kensington.
During her nearly two years without a home, Karen's family worried about her and went looking for her. Sometimes they found her, but "she wouldn't always accept help," said her mother.
Karen always had enough to eat. Some days it was only a Reese's Peanut Butter Cup. But lots of times, strangers brought her a sandwich or coffee. A worker from a restaurant on Chestnut Street regularly brought her full meals.
And all the homeless regulars on Market Street knew that about 7:30 each night, Dunkin' Donuts would throw out its day-old baked goods. Karen and the others would tear apart the bag and eat as much as they wanted.
When her money ran out, wasted on drugs, she panhandled. "People would walk by, throw a penny at you, give you the finger, or laugh," she recalled.
As harsh as some were, others displayed unbelievable kindness, Karen said.
"There was a girl, an African American, who pulled out a wad of money and said, 'Here.' She gave me a $100 bill. I said, 'I can't take that.' She said, 'Don't worry about it,' handed it to me and walked into the mall."
Then there was Roxanne, a white woman in her 50s who worked at Thomas Jefferson University Hospital and regularly slipped Karen a five.
Roxanne stopped by the day the puppies were born, Oct. 2, 2008. Karen had strung an old shower curtain between two Dumpsters behind Burger King. With Kenya stretched out on a blanket, Karen played midwife. The first puppy was born at 6:15 a.m.; the ninth and last at 11 p.m.
Roxanne took one look at a big pup and said, "He looks like a Buster to me."
And that's what they named him.
Karen gave away five puppies to people who saw her regularly, including two police officers and a woman who worked near the Bourse. The others she pushed around in her shopping cart, with Kenya, teats hanging low, walking beside her. Strangers brought Karen so many bags and cans of dog food that it created a bunker in front of Dunkin' Donuts.
The weather in the fall of 2008 turned cold early. On a windy, wet night, Karen was in the alley with her dogs when a woman named Emily approached her. She had a photo of Karen. Emily asked if she would like to move into an apartment of her own.
Not a shelter bed, but a real place to live.
"I can get you in an apartment in 10 days," the stranger insisted.
"Yeah, OK, whatever," Karen thought.
Emily Lattimore did outreach for a nonprofit agency working with the homeless, Pathways to Housing. They already knew about Karen. The city has a team of professionals who comb the streets each night, trying to persuade people to come in.
Those who had interacted with Karen thought she probably suffered from mental illness and addiction - the most common denominators among chronically homeless people.
Pathways had an offer: It would place Karen in an apartment, help her pay her rent using federal funds, and steer her to services to make her well. The agency wouldn't insist on sobriety. It could be a goal, but not a condition of staying in the program.
Best for Karen, she could take her dogs with her.
She had every reason to be dubious, but she was freezing and tired. Instead of turning away, she said yes.
On Nov. 17, 2008, Karen moved into a one-bedroom in Southwest Philadelphia. That first night, she slept on the couch in the living room, too disconnected to feel comfortable sleeping in a bed.
The arrangement didn't last. The landlord got fed up with the dogs.
Pathways moved her into a second place, in West Philadelphia, but that too was cut short. Still using, Karen violated the terms of her probation from a 2007 arrest for disorderly conduct.
She went to jail for 48 days.
As soon as she got out, she lapsed back to her old habit. "You can't force someone into sobriety," she said.
For a third time, Pathways placed her in an apartment - this one in South Philadelphia. She has been there more than a year. Unlike many programs, Pathways tolerates relapse and commits to working long-term with clients. "Once you're in, you're in," Karen said.
What pushed Karen into a drug-recovery program was a health scare that landed her in the emergency room. Doctors removed two large abscesses, stemming from her drug use. The procedure was so excruciating that it persuaded her to quit.
Now clean, Karen sometimes gets overwhelmed by the challenge of managing her mental well-being. She keeps in regular contact with a team from Pathways, which charts her progress and offers help when necessary.
On a recent morning before Christmas, Karen sipped a peppermint mocha in a Starbucks on Market Street. She wore a hot-pink down coat, a gift from her mother.
Her hair was in a neat ponytail, her blue eyes clear. She's put on a few pounds in the last year, a byproduct of better eating and living.
"What are you going to do?" she joked.
She passes her days as a volunteer at an animal rescue clinic or tending to the strays in the neighborhood. She likes to bake and surprised her therapist with a box of heart-shaped tarts, with cherry filling and creme de menthe candy bits.
She took a train to her mother's house for a holiday dinner. She had missed many family celebrations and was not about to be absent anymore.
Ricki Webb had looked forward to seeing her. She still could not believe the change. "We all say, 'We have her back.' "
See a video about Karen Webb revisiting the city streets she used to inhabit at www.philly.com/karenwebb
Contact staff writer Jennifer Lin at 215-854-5659, email@example.com or @j_linq on Twitter.