The R&B singer was a guest on the Parenthood star's podcast, Armchair Expert With Dax Shepard, and during their talk, the men both admitted to having cheated in former relationships.
"So, I have a horrendous history of cheating, f**king deplorable," confessed Shepard, adding that once ladies started noticing him in middle school, he "couldn't say no to them."
"Any attention from a girl, I had to have it at all costs," Shepard -- who has been married to Kristen Bell since 2013 -- told Legend, noting that the 41-year-old musician has "all these great cheating songs."
Legend shared a similar story as to how he started running around on women. "I think what happened for me, personally, you go through a lot of your life in your teens -- and I was like the 'two years younger kid than everybody' in high school and college, and so I just didn’t get a lot of girls when I was younger," he explained. “When I started to get that attention, I loved it. I just ate it up."
Legend said he compromised the infidelity in his head by not labeling the relationships. "I escaped ‘technically cheating’ by keeping my relationship ill-defined. But it was really cheating," he told Shepard. "I definitely was dishonest and selfish and just enjoyed this new attention I was getting. It was happening before I was famous but when I was kind of on my way."
The "All of Me" singer is now happily married to Chrissy Teigen and a father of two, and shares what the turning point was for him.
"You just realize you’re happier being honest,” he said. "You’re happier being faithful and being in love with one person. At a certain point, I just decided that person was Chrissy. I decided I wasn’t gonna mess with anybody else anymore."
Legend stressed, "It's so much easier. Your whole life is lighter. When you're able to be honest with a person and you aren't hiding texts ...your mind is freer."
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Relationship Goals! Kristen Bell and Dax Shepard's Greatest Couple Moments
Legend and Shepard also talked about the pressure of both being in marriages that are often labeled "relationship goals."
"I think, 'I could blow this whole thing up,'" Shepard admitted. "That's certainly something I've done. And now, the whole world is watching. There is a stress about that for me."
As for Legend, he says the attention on his marriage to Teigen makes him less stressed. "I feel like it makes it even more less likely that I would f**k it up," he explained. "Chrissy has however many million Twitter followers. If I were to do anything, it would be career suicide. It would be terrible. It just gives you another reason to not f**k it up."
Here's more with Legend and Teigen, who are now, more than ever, "relationship goals."