Oprah Winfrey may have ended her 25-year run as America’s favorite talk show host four years ago, but she hasn’t slowed down, making headlines with her new shows on OWN thanks to her interviews with celebrities including Danny Pintauro, Holly Madison and Ali MacGraw.

But longtime Oprah fans might really want a check in with her hairstylist of 30 years, Andre Walker. How longtime are we talking? “We started working together in 1985. We were both babies. I owned a salon in Chicago and Oprah had just started doing a local TV show,” he says. “When I saw her I thought this woman really has ‘it’ — but her hair was never consistent. So I sent her some flowers and a note saying, ‘I’d really like to get my hands in your hair.’ She called me the next day and the rest is history! There was no way either of us could have predicted back then what our lives would be like today.”

Oprah invited Walker on her show to talk about their latest adventures — and his brand new haircare line — and before the show airs, we chatted with him about all things Oprah hair. (You know you want to know.)

Ruven Afanador/Courtesy O Magazine

The mane behind her constantly changing mane (she’s had here’s the video evidence) has at least one look he never wants to see again: 1987’s layered bob. “Layered bobs were so popular then and I cut it so short where it sat right at her cheek line,” Walker tells PEOPLE. “She hated it, and I thought it was the greatest thing because it was a trendy hairstyle. Now, looking back at the photo she was absolutely right.”

Sioux Nexi/Courtesy O Magazine

Another look she’ll absolutely never go for again? Anything that could be worn under a plastic tiara. “She was going to a black-tie event and I had this idea for an updo,” Walker tells PeopleStyle. “I finally did it and she looked in the mirror when it was finished and said ‘I’m not going to the prom! I’m not the prom queen! What did you do to my hair?’ So I fixed it, but let’s just say she’s not very fond of updos.”

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Donna Alberico/Courtesy O Magazine

So what happens when Walker isn’t around to work his hair magic on her? “At night she pulls her hair up into a pony on the top of her head,” he says. “It’s a trick that I taught her because if you sleep with your hair down it becomes all messy the next morning, but pulling it up saves the style.” (She does that with natural or straight hair.) And you won’t see her with messy hair outside of the house either — even on “off” days, she’ll toss on a headband to look pulled together.

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And her at-home product arsenal comes, of course, from Walker’s own haircare line, the Gold System. “When I was developing the product, I tested everything on her,” adding, “I keep her fully supplied.”

Courtesy O Magazine

So what’s next for the dynamic duo? “I don’t think we’ve ever done auburn on her before. I think a nice red would be really interesting to do on her,” he shares. “But it would take some convincing. She would say ‘Get a red wig — let’s try that.’”

Be sure to tune in to OWN TV on Saturday, October 10th at 10/9pm to see Walker on Oprah: Where Are They Now and catch a sneak peek in the clip above!

Which hairstyle is your favorite? Which should Oprah never try again? Tell us your thoughts in the comments below.

–Colleen Kratofil