Dolores Jeanpierre, legendary waitress and historical figure, of Ole’s Waffle Shop, has announced she has retired from waitressing on Dec. 14. She last worked at Ole’s in December 2020 when indoor dining was shut down again.

During this time, she fell off a ladder in her apartment, hurting her back, and developed other various health issues, although somewhat minor. Consequently, she needs to use a walker. She has been asked to come back to Ole’s at various times this year, but her health issues precluded her ability to come back to work. As the months have gone by, it has become more apparent that her career as a waitress has come to an unceremonious end.

Dolores was born in New Roads, LA. in 1951. She picked cotton when she was 10 years old. In the 1960s, she was among the first group of blacks who integrated Poydras High School in New Roads. She graduated in 1969. After graduating high school, Dolores became a cashier at a grocery store and from there, her sister was able to get her on staff at Tulane University in New Orleans, La. where she worked in the library in the Acquisition Department. A year later, she married a soldier who had just come back from Vietnam in the 82nd Airborne. They met while he was stationed in Fort Bragg, NC. He was transferred to Fort Ord in California in May 1972. They drove from Louisiana to California with their son Travis, who was 7 months old at the time.

Dolores started out as a waitress at Swan’s Market in Oakland. Swan’s had a small counter in the store that served breakfast and lunch, so she applied as a waitress and got the position. She had never been a waitress in her entire life. One day, the owner’s sister, who worked at Nikko’s Restaurant in Oakland, was short of help and called her brother, Dolores’ boss at Swan’s, and asked for help. He sent Dolores to Nikko’s to help his sister at her restaurant. Dolores worked there for two days, and the owner of the restaurant, Nick Calais, called her boss at Swan’s and told him that Dolores wasn’t going back there, that he was going to keep Dolores at Nikko’s! Towards the end of 1977, Dolores was working at a beauty salon in Berkeley, when her late friend Darlene Walker, told her that Ole’s Waffle Shop in Alameda was hiring. Dolores went to Ole’s Waffle Shop, and she was hired by Christie Adams, the owner of Ole’s.

Dolores started working at Ole’s on June 5, 1978. It should be noted that at that time, there had been no waitresses of color in Alameda. She was also the first waitress of Creole descent in Alameda. While it is certainly something to be proud of, it is not something that Dolores wears on her sleeve. She realized almost instinctively that it doesn’t matter who you are or who the people are you’re serving. They all want good service, good food and a server with a smile.

Dolores developed quite a following in Alameda and surrounding areas. Customers came to see her, even after they moved away from Alameda.

Dolores became known nationally after the publication of the book, Counter Culture: The American Coffee Shop Waitress, by Candacy A. Taylor in 2009. In the book, Taylor traveled around the U.S., visiting local coffee shops with local waitress legends. When she came to the Bay Area, she was told about Dolores! Dolores was prominently featured, with several pictures and quotes throughout the book.

In addition, Dolores has been featured in local newspapers and magazines. She was voted Best Waitress in the City of Alameda in 2007. She was featured in the PBS program, California’s Gold. That show, which can still be seen online, begins with Huell Howser talking with Dolores in the middle of Ole’s!

In 2016, the San Francisco Chronicle did a feature (“Side of charm on the house from coffee shop veteran,” May 16, 2016) and video on Dolores and Ole’s Waffle Shop. He was there early in the morning before Ole’s even opened. The video was posted in an online version of the paper and has since received several hundred thousand views!

Dolores did leave waitressing for a time. She was hired immediately in 1982 by Filippelli Bail Bonds. After taking the state exam for bail bonds and passing it, she became a bondsman on August 2, 1982. In January of 1996 she put her home in Fremont up as collateral with the surety company, and opened her own bail bond company, starting from scratch on her own. She named it Alameda Bail Bonds. She had that business for more than 25 years and was a licensed bail bondsman for more than 38 years. She contacted Vickie, the owner of Ole’s Waffle Shop, and asked her if she could come back to Ole’s as a full-time waitress in addition to keeping her bail bond business on the side. Vickie said a most definite “yes”, so Dolores made her return to Ole’s.

When she decided to return to waitressing in addition to still working as a bail bondsman, she was asked “why do you want to go and carry plates again?” Her answer, while initially focusing on compensation, then developed into a conversation as to why she enjoyed being a waitress. Dolores is a real people person, when you get down to it. This is the reason for her success, above all else. She is well known, for engaging in conversation with customers at Ole’s, and continuing those conversations, as she goes all over the restaurant, keeping coffee mugs filled, and attending to various customers’ needs. In doing this, Dolores actually brings customers together and totally enhances the Ole’s experience, thereby creating the ambiance that Ole’s is noted for!

Dolores will be missed by all Ole’s customers and the Alameda community. People can drop off cards or gifts for Dolores to Ole’s and they will make sure that Dolores gets them.