"Don't you meet a lot of guys? Where do you go at night?" Stewart asked, confused why the 48-year-old was struggling in the dating department, to which Barrymore quipped: "Home."
"Don't you go out to dinners and parties and stuff? Your friends have to be sitting you next to eligible young men," the businesswoman pestered, prompting the talk show host to respond, "No I'm not living that life, Martha!"
"Well, you better start," Stewart warned. "You have a lot of friends and they should be inviting you to eat. They didn't do that for me either, by the way, I had to do it myself."
Circling back to the cookbook author's steamy love life, Barrymore pried Stewart for more dirty details about her recent romantic interaction.
- Martha Stewart Fans Confused by Her 'Ridiculously Photoshopped' Ankles in New Photo: 'Really Not Necessary'
- Martha Stewart Gushes Over Easter Weekend Visit With Pete Davidson & Girlfriend Chase Sui Wonders: 'Very Cute Couple'
- Martha Stewart Gushes Over Pete Davidson's 'Lovely' New Girlfriend Chase Sui Wonders After Admitting She'd Date the Comedian
Never miss a story — sign up for the OK! newsletter to stay up-to-date on the best of what OK! has to offer. It’s gossip too good to wait for!
"It wasn't exactly appropriate, but it was good for a night," Stewart candidly admitted, noting: "Nothing happened, nothing happened. We didn't go home together or anything, but it was just like a little flirtation. It's nice."
Elsewhere in the episode, the E.T. the Extra-Terrestrial actress revealed one of her pet peeves when it comes to dating.
"I had a relationship with a guy who just napped all the time, it made me sick to my stomach. He was just so tired all the time, he would nap all the time," Barrymore explained, however, Stewart disagreed, insisting she was totally up for a good nap on occasion.
"Would you date a man who didn't work and naps all the time?" Barrymore comically reiterated, as Stewart questioned: "Didn't work?"
"Did I say that out loud?" Barrymore joked.
"Yes," the celebrity chef replied, adding: "No I would not. That's not what I do. A nap when you're tired is good, catch up."
Stewart concluded: "If he were the most fabulous man in the world and I was madly in love with him and he wanted to take a nap every now and then, that's fine with me."