Actress Jennifer Love Hewitt smiles for photographers as she arrives at the Hollywood Film Festival Awards 2008 Honoring Clint Eastwood on October 27, 2008. This was at The Beverly Hilton in Beverly Hills, California. Clint Eastwood turned a mere 78 years old that year, and Jennifer Love Hewitt turned 29. According to the IMDB, Hewitt and Eastwood have never worked together, although they have appeared on the same TV awards shows, like the 2007 Golden Globes telecast. If you're cynical, you might say that it's remarkable that Hollywood missed a chance to pair a 78-year-old man with a 29-year-old love interest. But that would indeed be cynical, wouldn't it?