When that doesn't work, she looks for help from the people who surround her -- her attorney, her financial planner and the personal assistant employed by the nursing home in Ladue where she now lives. Other than that, there's nobody. She has no children, and her husband, Frank Dempsey, who was a barber, died years ago, sometime in the 1970s -- she can't remember exactly when.
She also can't remember how much money she actually has, and sometimes she loses track of where it's all going. Her attorney, Eric Taylor of St. Louis, reminds her that he's set up a trust fund that will donate $10,000 in her name to local charities every year, but then she stares at him for a few seconds as though she's trying to figure out exactly who he is.
Mrs. Dempsey does remember that she doesn't remember so well anymore. Like most people who've earned the right, she's not apologetic. "Don't ask questions like that," she says, for example, when asked how old she was when she first went to work. "It was too long ago."
Her attorney and trustee of the fund is intimate with the paperwork and fills in some of the blanks. "It would have been between 1915 and 1920," he says, looking down to Mrs. Dempsey, who, from her wheelchair, nods back up in belief.
But slowly it starts coming back: She dropped out of school in the eighth grade and went to work for Southwestern Bell as a stenographer when she was 15. At the time, she lived in North St. Louis with her parents and older sister, Stella, and after giving her family a small portion of her paycheck every month, she put the rest into her savings account. She doesn't remember how much. When she had enough in her savings account, she took it out and bought a bond. Then she took the bond and tucked it into a safety-deposit box. And so it went, month after month, year after year, for more than 50 years.
"I just didn't spend money on things I didn't need," Mrs. Dempsey says. "I'm just of that character. I didn't want to worry about the future, so I just saved whatever I could."
In her lifetime, Mrs. Dempsey never went away on vacation, never bought a car and never, never gambled. "It all went into tax-free bonds," she says. "Missourah tax-free bonds." She and her husband lived frugally -- "I had no trouble with him," she says, smiling -- but they managed to buy a three-bedroom house in North St. Louis and caved in occasionally to the lure of ice cream and the movies. She says she never felt deprived of anything, because she took so much pleasure in just saving the money.
"I think you can live simply and enjoy it," Mrs. Dempsey says, "because if you splurge, you pay the consequences."
After her husband died, financial adviser Jim Richardson of St. Louis stepped in to help her with her taxes. "She kept notes on everything," he says, smiling down at his client, who stares off at the middle distance. "And she had all of her paperwork in shoe boxes in her closet. She kept everything very well organized."
Mrs. Dempsey lived on her own in the house for another 20 years, with Richardson keeping track of her expenses. She walked to the grocery store, ate simple meals and eventually realized a personal net worth of several million dollars. Richardson asks that the exact amount remain unpublished. "Let's just say she's amassed great wealth," he says.
But Mrs. Dempsey had lived so carefully for so long that she couldn't bring herself to start spending the money. There was no place she particularly wanted to go, no jewels she coveted, no grandchildren to pamper. "I'm just not that way," she says with a shrug.
But two years ago, Mrs. Dempsey started losing her balance, and, after a while, she realized she couldn't live on her own anymore. With her own mortality facing her for the first time, she also began thinking about what would happen to all of her money. She talked it over with Richardson, who talked it over with Taylor, and they agreed to create the Olive Dempsey Trust Fund.
Last week, with the nursing home swarming with reporters, television-news crews and photographers, Mrs. Dempsey handed over the first $10,000 award from her trust to Randy Grim, founder of Stray Rescue of St. Louis. Because she couldn't remember what the organization did exactly, Grim leaned down in front of her and explained.
"We rescue stray dogs that have been abused," he said as the media hovered closer. "We take them in and try to rehabilitate them so they can go to loving and permanent homes."
In an adjoining room, a piano struck up "Yankee Doodle Dandy." Mrs. Dempsey smiled.
Grim nodded: "This money you've donated to us will go toward fixing up a building we have. We'll be able to keep some of the dogs there, where they'll be safe and well taken care of."
"What will you do with them?" Mrs. Dempsey asked.
"We'll try to teach them to trust people."
Mrs. Dempsey smiled again and looked up at the reporters, photographers, attorneys and consultants standing all around with a look that said she had just lived the best 95 years of her life.
"You mean," she finally said, "you will teach them how to live."
The young man in front of her nodded.
"That's good," Mrs. Dempsey said. "That's very good."
In the background, "Yankee Doodle Dandy" played on.