The star is best known for romancing Krugers, who has starred in Troy and Inglourious Basterds with Brad Pitt.
He also dated Katie Holmes for a while as they filmed their series in North Carolina in the 1990s.
"It would be so hard to start dating again after 10 years," host Ellen De Generes said.
Jackson agreed that it's been an interesting adjustment, saying, "Things have change a little bit since last time I was single.
The pair were seen strolling arm-in-arm past a convenience store that sold vapors and Lottery tickets.
And they were also enjoying a meal inside a cozy restaurant.
"I think it brings up uncomfortable conversations." Filming her own sex scenes is bad enough.
Joshua Jackson split from Diane Kruger eight months ago after being in a 10 year relationship with the German-born movie star. "So, yeah, it's been quite a big change."De Generes suggested he should try a dating app or a dating website, but he wasn't sure that was realistic.Joshua Jackson and Diane Kruger proved that love is dead when they announced their breakup after 10 years of dating earlier this week. Diane Kruger is open to finding love after splitting from Joshua Jackson.The Bridge actress joked about her relationship status at the Cinema and Chopard Society screening of her film Disorder in NYC on Tuesday, August 9. "To his surprise, De Generes had plenty of vintage pictures from teenybopper magazines he could use on his profile. "You're adorable all the time.""You see adorable; I see embarrassing," Jackson laughed. To De Generes' dismay, Jackson revealed there is less nudity this year. I just walked around naked."Perhaps Jackson can use , to actually see us on camera again might be a little bit shocking and kind of heartbreaking.