Some try to distance themselves from it. Others refuse to acknowledge songs they recorded when they were 16. Some get angry whenever they're asked about their teen stardom.
Now 43, the singer/songwriter (full name: Tiffany Darwish) is in a good place. She's got a trendy, funky boutique in Nashville. Her son, Elijah, is grown. She's giving back to charities. And, she says, she is working on new music.
Tiffany was all smiles at the PEOPLE Magazine VIP Party at Hearts of Reality, an weekend event in Celebration, Florida that raises money for children's charity Give Kids the World
As Tiffany wandered through the gifting suites full of swag provided by Ava's Cupcakes and Udderly Smooth body cream, dozens of reality stars approached her for photos. (It doesn't get more surreal than seeing Tiffany posing for photos with Bachelorette contestants.)
Sitting with PEOPLE at Melia Orlando Suite Hotel at Celebration, Tiffany opened up about her past pop stardom – and her future plans.
Tiffany's BoutiqueAbout three years ago, Tiffany decided to branch out. She opened Tiffany's Boutique in Nashville. The boutique has an eclectic array of fashion, from vintage to modern.
"I thought, 'Wouldn't it be cool to open up a boutique that is a little bit of glamour, and a little bit different?'" she says. "I work with local designers around Nashville, and buy different items from around the world that can be tailored."
"I'm a real girl. I get it," she says. "I gain weight, I lose weight. My styles change. My goal is to provide fashion for real women – any size, any age. I'm budget conscious; my things don't cost a fortune. But it's a way for people to feel good about themselves, based on how they are dressed."
"Obviously, I wore a lot of crazy things on stage. That's just how it goes," she adds. "So I like a lot of stuff that is stripped down and comfortable."
The Jazz SingerAlso stripped down: Tiffany's music. She's still writing songs and releasing albums – just on a smaller scale than she did in the late 1980s.
It's a startling departure from the manufactured pop princess who drew huge crowds to her Tiffany Shopping Mall Tour '87 and sold four million copies of her self-titled debut album.
"For a lot of people, I will always be the mall girl, and that's okay," she says good-naturedly. "That was my start. But I can do so much more than that. My voice has matured; I've developed as a songwriter. And I want to show that off."
To that end, Tiffany is working on a new album. "It's a stripped-down, live in-studio acoustic album" she says. "There's not a lot of production. I'm inspired by jazz. I love small venues when people just sing and really connect with an audience. That's what I want to do next."
And what about the people who want her to sing one of her old hits like I Think We're Alone Now? "I'll do it," she laughs, "but it has to be acapella."
"What I want," she continues, "is for people to walk away saying, 'Wow. I didn't know she can do that.' That would be a huge compliment to me. And I finally have the confidence to say that I actually can sing really well, and I have a lot to offer."
Giving BackWith her 23-year-old son, Elijah, now grown, Tiffany is also giving of her time to charity. She spent her weekend raising money for Give Kids the World, interacting with the kids and signing autographs to raise funds for the charity. (When the autograph line became longer than expected, she refused to leave until the last one was signed.)
Later that evening, she gamely attended an '80s party at Celebration Town Tavern, although she didn't take the karaoke stage. (She's under contract with Disney for the upcoming Food and Wine festival, and can't sing her old songs publicly for the next 90 days, or else she totally would have grabbed a microphone.)
"It's so important to give back," she says. "When you see children's charities like Give Kids the World, you have to help. If I just go about my life and don't give back, what good is that? So it's very important to me."
"I've had a good career," she continues. "And I've had the good fortune to do very well. Giving back is the right thing to do."
And is she happy?
"Oh, yes," she replies. "There are so many great things coming up. I can't wait!"