Jake has dated a laundry list of Hollywood hotties, from Taylor Swift and Kirsten Dunst to Reese Witherspoon and Natalie Portman. If the diversity in this list is any indication, Jake must have a wide range of appealing attributes (in case his good looks aren't enough to win Katie). Plus, he's good with kids. Jake frequently babysits his niece, sister Maggie Gyllenhaal's daughter Ramona, and he's the godfather of Michelle Williams' daughter, Matilda. So the "Love and Other Drugs" star should be perfectly at ease with Katie's daughter, Suri.