Lindsay Shookus and Ben Affleck (With a 8-year age gap)
Ben Affleck has been in the news recently for rekindling his legendary love with Jennifer Lopez. They appear to be happy, although Affleck has had multiple relationships with younger women between his divorce from Jennifer Garner and now.
Lindsey Shookus, a Saturday Night Live producer, was one of them. Even though the age difference was only eight years, it could have been a deal-breaker. Although the relationship didn’t last, Ben moved on to younger ladies.