Sean Penn

What Charlize Theron Is Saying About Her “Effortless” May-December Relationship with Sean Penn

How long do you need to really get to know some­one? Char­l­ize Theron, 38, has finally opened up about her May-December rela­tion­ship with actor Sean Penn, 53, and it turns out that this celebrity couple’s love story was almost two decades in the mak­ing. Theron and Penn started dat­ing seri­ously in Feb­ru­ary 2014 and their 15-year age dif­fer­ence was hardly an issue, because they were good friends for 18 years before they […]

Look Who Sean Penn Picked to Replace His Ex-Wife (Hint: She’s Much Younger!)

Sean Penn, 53, recently cast his new younger girl­friend, Char­l­ize Theron, 38, as the female lead in his upcom­ing movie The Last Face. That’s not too shock­ing, con­sid­er­ing this celebrity cou­ple hasn’t been able to tear them­selves away from each other since going pub­lic with their May-December rela­tion­ship. But what is sur­pris­ing is that the role actu­ally belonged to Sean Penn’s ex-wife, Robin Wright, first. In fact, the whole film started as […]

Charlize Theron and Sean Penn Caught Making Out (at His Ex-Wife’s Oscars Party!)

Char­l­ize Theron, 38, and Sean Penn, 52, are the hottest new item in Hol­ly­wod, and they appar­ently want every­one to know about it. The celebrity cou­ple showed up together at the annual Oscars after party hosted by none other than Penn’s ex-wife, pop queen Madonna. And accord­ing to wit­nesses, Penn and Theron couldn’t keep their hands off each other. The celebrity cou­ple was report­edly “mak­ing out like crazy” and were “all over each […]

Sean Penn and Charlize Theron,15-Year Age Difference

Sugar Daddy Sean Penn and Charlize Theron

Sean Penn, 53, is no stranger to high-profile romances. The 50-year-old Oscar-winner was once upon a time engaged to pop queen Madonna. The celebrity cou­ple tied the knot in 1985 and their mar­riage was wrought with vio­lence, mostly due to Penn’s wild tem­per. In 1986, he attacked musi­cian David Wolin­ski for hit­ting on his famous wife in a night­club, for which he was charged $1,000 and slammed with a year-long pro­ba­tion period. […]