The results were as revealing as they were funny.
The rules were simple. Every time a "Never Have I Ever" statement was false, Stewart had to take a sip.
The first statement was "Never Have I Ever Regifted A Bottle of Wine."
"Not true," Stewart said, taking a swig. "If it's a bad wine it gets given away."
Next up was if she had ever kissed someone on a first date.
"Not true," Stewart said while shaking her head. "How else are you going to get to know them fast?"
Stewart married Andrew Stewart, then a student at Yale Law School, in 1961, and the two stayed married and had a daughter before divorcing in 1990. She's previously dated Anthony Hopkins and billionaire Charles Simonyi, but she broke up with the latter back in 2008.
Next up she was asked if she ever used Tinder, Bumble or any other dating apps.
"No I use Match.com (which also owns Tinder), to great disappointment," Stewart said. "They just don't make algorithms for people like me. I'm a complicated date, for god sake."
She then was asked if she'd passed off takeout as one of her own dishes, but she said she'd "never do such a thing." That was followed up by asking if she'd ever dined and dashed before, to which she said "I do it all the time."
Stewart was then asked if she ever searched her own name in Google
"I have Googled myself, I Google myself every now and then," Stewart said. "It's very important. 'Martha Stewart pierogies' used to get more impressions than 'Martha Stewart,' so you can figure that one out."
Other things Stewart admitted to doing included googling her ex-boyfriends, calling a celebrity by the wrong name, eating a frozen TV dinner, double dipping and going on back-to-back dates in one night.
But despite her friendship with rapper Snoop Dogg, Stewart claimed she's never smoked weed in her life. The duo's surprising friendship led to the VH1 variety show Martha & Snoop's Potluck Dinner Party, which concluded its second season in November. Guest stars from the eight-episode second season included music and entertainment stars like Sharon Osbourne, George Lopez, Wendy Williams, Post Malone, LL Cool J, Kate Upton, Usher, Jamie Foxx and Jeff Ross.