People reports a source confirms, "Ben reached out to Jennifer as a friend. He was basically checking up on her."
While he may have been acting as a friend, "He was single and thought she might be single, too."
Turns out she wasn't — the 51-year-old icon was still with Alex Rodriguez, and engaged to be married to him. Still, they'd announced they were "working through some things," and within weeks, their split became public.