Martha Stewart Shares the ‘Deal Breaker’ She Learned From a Bad Date

The lifestyle guru recalled an unfortunate story while on ‘The Drew Barrymore Show’ today.

Martha Stewart / Katie Jones/Getty Images

On a recent episode of The Drew Barrymore Show, Martha Stewart shared a surprising dating revelation that had the audience both laughing and nodding along. Known for her culinary expertise, business acumen and impeccable taste, the history-making SI Swimsuit cover girl, who posed in the Dominican Republic for the front of the 2023 issue, also has a knack for setting boundaries and knowing what she’s willing to compromise on when it comes to romance.

The 82-year-old chatted with SNL alumnus Ana Gasteyer, who was dressed as Stewart herself— down to the wig, glam, outfit and soft smile.

View this post on Instagram

A post shared by The Drew Barrymore Show (@thedrewbarrymoreshow)

"You look better than I look, darling!” Stewart joked when the actress crashed her interview with Drew Barrymore and surprised her with an identical look. “My impersonator, I fear for her.”

The women began chatting and the comedian asked Stewart to share her worst date story.

“Oh, I have had so many bad dates. I can’t even enumerate. I went out to dinner with one guy and this was when I was doing those dating apps. I was forced to do those for a gig,” she began. “We went to a very hard, hard, hard-to-get-into restaurant and we were treated extremely nicely. “And although we didn’t even have to pay because it was part of the gig, he didn’t leave a tip.”

The live talk show audience was quick to react with booing and “awww.”

“That was no good,” Stewart agreed.

Barrymore chimed in for a second to ask if the date seemed “promising” up until it came time to pay the bill. And, without hesitation, Stewart responded “No. That sealed the moment.”

“Bad tippers is a deal breaker,” Gasteyer added.

View this post on Instagram

A post shared by anagasteyer (@anagasteyer)

Stewart got married to ex-husband Andrew Stewart in 1961 and the couple officially filed for divorce in 1990. They share one daughter, Alexis Stewart, and two grandchildren, Jude and Truman.

The 100-time New York Times best-selling author’s family life and rise to fame were also highlighted in the new Netflix documentary Martha, which delves into her journey from model to media mogul and was released on Oct. 30. The film offers a rare glimpse into her personal life and the relationships that shaped her remarkable career.

Stewart’s 100th cookbook Martha: The Cookbook: 100 Favorite Recipes, with Lessons and Stories from My Kitchen released today, and is available on Amazon, QVC, Williams Sonoma and her publisher, Penguin Random House‘s website.