Andie MacDowell needs no introduction thanks to her work in classic films like Groundhog Day and Four Weddings and a Funeral. In recent years, however, you may have noticed that she’s refused to resign herself to quiet retirement. In fact, she’s continued to star in critically acclaimed films and has taken to strolling down runways in her spare time. It turns out that MacDowell has been purposefully challenging her 90s starlet reputation to remind us that actresses don’t expire at age 40.

To celebrate starring in the heart-wrenching new movie, My Happy Ending, MacDowell sat down with Katie for an honest chat about double standards in Hollywood and why she’s chosen to fearlessly embrace age (seriously — her gray hair will want to make you ditch your hair dye). Plus, they get into the nitty gritty of dating in middle age and why there are some serious benefits to staying single.

Read highlights of their conversation below but watch the entire video to get the full story.

Katie Couric: You’re really having a moment, but your career has been a long one. I remember you in Groundhog Day and Four Weddings and a Funeral. Can you believe those movies came out almost 30 years ago?

Andie MacDowell: Yes, I can. Working in your 30s is fantastic. In my business, getting cast is so much easier in your 30s, and then it gets tougher. I remember turning 40 and going to a film festival and having a young woman interview me. One of her questions was, ‘How does it feel to get older and lose your beauty?’ She actually said that to me. It made me sad for her because all I could think was, You’re going to be me someday. Why would you even think that?

So many of my single friends in their 50s and 60s complain that men their age want to be with women in their 20s and 30s. Does it frustrate you that eligible men around your age would want to date 20 or 30 years younger?

It’s not new. This has been happening for a long time. [Men] have had that right and privilege. They’ve been fed it. I think stories that we tell, particularly in movies, have an effect on people. It sets a standard for the choices that you have in society. If you do it for a woman, it’s got to be some crazy story. It can’t be normalized at all. And [what people see on-screen] does have an effect on the choices people can make.

I don’t want to take on somebody 20 years older than me. I have no interest in that whatsoever. That sounds like a terrible job. I like to hike and have a good time. If I were to get back into a relationship — and honestly, it’s not that important to me, it would be a miracle if it happened — it would have to be with a contemporary. I’m not really interested in somebody much younger than me, either. I’m too affected by our culture.

I can’t get frustrated with what the facts are. It is what it is. I think I’m more frustrated that I can’t be comfortable with someone who’s 20 years younger than me because I’m so affected by our culture. It’s so deeply ingrained in me that I wouldn’t be comfortable. I know Cher’s dating younger and I’m so glad for her. I’m glad she’s comfortable doing that. I think it’s fabulous…I wish I could make that choice. I joke about it, that’s about as far as I go.

I’m not even dating. I haven’t dated in such a long time, but miracles do happen. It’s still possible.

Your latest movie, My Happy Ending is about an actor who’s diagnosed with stage four colon cancer. She’s living in London and she’s facing her own mortality. Why did you want to make this movie?

Well, the character was fascinating to me. But what I enjoyed about it was the camaraderie of the women and the connection they had when they were getting their treatment. Because cancer is the great equalizer. And you had these women from all different walks of life sitting together, getting chemo, and helping and supporting one another. I found that incredibly moving.