The actors briefly dated in 2007 before mutually calling it quits
Though the romance was short-lived — they split after just a few months — the former pair looked back on their time together, which they admitted had “started as a joke,” with extremely fond memories.
“First of all: very, very fun. [A] very memorable, very wonderful, fun experience,” Shepard, 44, said of his relationship with Hudson, to which she added that it was “a blast.”
The actor explained that he and Hudson first met in the backyard of Tobey Maguire‘s house and immediately hit it off, but both were in other relationships at the time. (Hudson was married to Chris Robinson and Shepard was dating Briegh Morrison.)
“We were in a totally different place,” Hudson explained, as Shepard jokingly added, “I wasn’t plotting anything but I certainly wanted your approval and if you thought I was cute, all the better.”
About a year or so later, the pair reconnected at a restaurant in Malibu — shortly after Hudson had ended a relationship with her You, Me and Dupree co-star Owen Wilson — and decided to mess around with the paparazzi waiting outside.
“While we were there, we said, ‘Wouldn’t it be funny if we came out holding hands and I was your new boyfriend?'” Shepard recalled. “We were just pals.”
“And then we added, ‘Wouldn’t it be great if her new boyfriend didn’t wear a shirt at Nobu?'” the Parenthood alum added.
So they went for it, completing a hilarious stunt that Hudson said was “so funny” that she almost “peed in my pants.”
“I was acting mad at the paparazzi that they were invading our privacy,” Shepard explained. “And then it just somehow led to hanging out!”
“Then I wanted to have sex with him,” Hudson jokingly added. “It was like the perfect move.”
While they were dating, Hudson noted how their personalities were “super compatible” and that “we laughed our asses off.” Shepard also credited their romance for helping him communicate better, especially amid the blowout fights they frequently had, and for leading him to become monogamous for the first time in 15 years.
But ultimately, Shepard said, the pair “just parted ways.” Hudson added that their break up was a “mutual-esque end” and due to how she and Shepard “were in different places in our life.”
“I felt very ‘less than’ around you quite often,” Shepard admitted. “I think I was just in the point where I was not gonna get hired for movies anymore — I had a bunch that didn’t work — and I’m like, ‘I don’t f—ing know what’s next’ and you were at that time making the most you ever made and having the most opportunity.”
“I felt very much like, ‘F—, I don’t know what I’m doing,'” Shepard added of Hudson, who at the time had just starred in How to Lose a Guy in 10 Days and Almost Famous. “I’m following this person around as they do things I wish I were doing. It was a rough period anyways and then I felt all kinds of inadequacy in that position.”
“But you also said that you really wanted a ‘we’ in your life and that you felt that it was just about me,” Hudson chimed in. “Honestly, I wasn’t giving Dax what he needed and I was making choices that were not relationship-focused.”
“It was a lot fast,” she added. “I was not ready for what Dax — It was so much fun, it got hot fast… and I wasn’t prepared.”
Shepard also said that he was looking forward to settling down with someone and having kids — something that Hudson had already done with Robinson (the ex-pair welcomed son Ryder in 2004) and wasn’t exactly ready to do again.
“I was 32 going, ‘Whoever I date next has to be the one, I want to spend three years with somebody to know I want to have kids'” Shepard revealed. “I was ready to have kids and do it.”
Besides chatting about her former romance with Shepard on Monday’s episode, Hudson also discussed her recently-launched Sibling Revelry podcast with her brother Oliver, 43.