What would you do differently about losing your virginity?
Jon Hamm: "I don't know. Everything? [Laughs] There's no version of it that's not awkward. Let's put it this way: As much as I had practiced, I was still not quite ready for game time."
Were you very young?
"I wasn't. I was in college. I was 19."
That surprises me.
"I don't know why that would surprise you. Maybe it's easy for some people. It certainly wasn't for me."
You play the ideal male specimen in 'Keeping Up With the Joneses.' But you're famously self-deprecating. You've said, "I'm no Ryan Gosling."
"I don't know Ryan. He's impossibly handsome. But I remember having a meeting with the director and writer of Keeping Up With the Joneses and saying, "There are a couple of ways to play this guy." I think the more interesting thing is to have this guy who seemingly has it all, but it doesn't make him happy. A lot of people get lost in work. He wants something in his life that's authentic. [Laughs] Which is admittedly a not-so-funny way to enter a comedy. For most people, the authentic things are relationships, friends, and family."
What did your dad teach you about women?
"He was twice widowed. He was divorced from my mom when she died, but even so, there's a deep sense of tragedy in that. I never had the opportunity to, as an adult, sit down and talk to him about that. It's a real loss. I was quasi-adopted by my friends' families. And even today I get e-mails or cards from these women who, for lack of a better word, were my mom. We talk about what it means to be a family. Mostly it's about showing up. And being aware enough to check in and say, "How are you doing?" I've been incredibly lucky to have these people in my life."
What do you wish you could tell your 20-year-old self?
"I do think about that. The best thing you could say is: Appreciate it. Struggle is part of the journey. That's what I've learned in my forties: This too shall pass."
What do you want to tell the next woman who dates you?
"Oh God. I don't know. I don't think I'm ready to answer that yet."