Both are Hollywood A-listers whose high-profile relationships have taken up a lot of bandwidth over the years, so perhaps it was inevitable that one day Reese Witherspoon and Jake Gyllenhaal would get together. While the romance turned out just to be a pitstop for both of them en route to longer lasting love, it was a pretty big deal at the time. Let's cast our minds back ... How It Began In 2006, Witherspoon was turning 30 and newly separated from Ryan Phillippe after seven years of marriage.