I recently saw Up Close and Personal, a 1996 movie where Michelle Pfeiffer plays Tally, an ambitious reporter-to-be, who works hard and lands herself a gig at a TV station. She is at first just answering phones and taking notes and making coffee, but she manages to prove to her mentor, seasoned reporter Warren Justice (Robert Redford) that she is talented and hard-working enough to appear in front of the camera. The two form a very close relationship, but they don’t let things get romantic until it is time for her to move to another city for her promotion. From then on, they both do everything they can to be together and manage their careers at the same time.

During the making of the movie, Robert Redford was 60-years-old and Michelle Pfeiffer was 38. The story was well-told, intense, romantic and heart-felt and they seemed like the perfect couple. The age difference wasn’t distracting.

13 years later, in 2009, Michelle Pfeiffer starred in the film Personal Effects, a movie written by David Hollander (creator of the TV series The Guardian starring Simon Baker). Her co-star was Ashton Kutcher. Ashton played a 24-year-old in the movie, despite being 31 at the time. Michelle’s character’s exact age is not revealed, but her real age was 51 at the time, making Ashton 20 years her junior.

Personal Effects doesn’t start as a love story, but rather as an incidental friendship when the wife of a murder victim meets a young man whose sister was murdered. The woman has a troubled teenage son, who also happens to be deaf and mute. While Ashton’s character waits for the verdict of his sister’s trial, the two get to become friends, shoulders to lean on and eventually lovers.

Similarly in 2009, Michelle also had a much younger on screen interest in Chéri, where she played an expensive escort falling in love with the son of her former colleague. The son is played by Rupert Friend, an English actor who you might remember as Mr. Wickham from 2005’s Pride and Prejudice movie. Friend was born in 1981, which makes him 3 years younger than Kutcher. Incidentally in both Personal Effects and Chéri, the boys’ mothers are played by Kathy Bates.

In 2007’s I Could Never Be Your Woman, Michelle again played a woman falling in love for a younger man. However, Paul Rudd is only 11 years her junior, so I didn’t include him to this list.

13 years after having played the love interest of an actor who was 22 years her senior, Michelle managed to play the older lover of two actors, who were respectively 20 years and 23 years her juniors. Some may say history opposed itself. Some may say it may no longer be that bad to be an aging (beautiful) actress in Hollywood.