I suppose one of the biggest bits of advice you give in your book happens to be in the very first chapter, where a friend of yours is struggling with the idea of marriage on her wedding day. Why open the book with that story? ALI WENTWORTH: Because it’s the predominant thing I think I give advice about most, which boils down to really listening to your gut, but for women I needed a really good example of it. That seemed like the best example, because I’ve had so many friends who’ve felt, “I don’t really know what I’m doing” or “I don’t even know if I want to do this.” I certainly remember when I was younger, being at a bunch of weddings and thinking, “This is crazy. Why are people still compelled to do this?” Or when they knew they shouldn’t do it, it was, “Well, we already sent the invitations out.” And my feeling you’re going to save a lot more than however it costs to feed people at your wedding, than a horrible divorce five years from now. But this seems like everyone has been there, it may not be about getting married but you know in your gut you shouldn’t do something, but did it anyway.
There are some pretty funny stories in this book, but I heard a rumor that you once threw a package into Donald Rumsfeld’s yard. Is that true? AW: Yes, that is true. I was invited to his Christmas party and we were talking about this essay by E. B. White, cause we both loved his books. And the next day I was in Uggs and sweatpants and I was running errands, and I stopped by Barnes & Noble and bought one of his books. I thought, “What a nice thank you gift.”
So I got the book and when I went to his house, I suddenly felt like I couldn’t ring the bell, because I was in sweatpants and looked horrible, so I threw it over the wall. So, of course, the gardener or somebody else got it and was surrounded by guns. That night I said to George, “You’re not going to believe what happened to me today…” And he said, “You didn’t think throwing a brown package over Rumsfeld’s fence during war was an bad idea?” So yeah, I did do it.
Speaking of George, how did you two meet? AW: I grew up in D.C. and I grew up amongst political guys, so George Stephanopoulos was not what I was looking for. I did everything I could to get out of that world. I was in LA and he was in New York, and I thought next time I’m in New York it’d be a great dinner party story. So I called him up and he said, “What about dinner?” and I said, “What about coffee?” He said, “What about lunch?” and I said, “Okay, what about Barney’s?” Beause I could get my Kiehl’s scrub, if it was a total bust.
I didn’t shower. I wore a black suit, so I looked smart, and read the New York Times. I thought it’d just be an interesting lunch, but we were married two months later, and have been married over 17 years now.
What was it in that first encounter that made you know it was right? Or, did you know from that moment? AW: Well, this is the big question. It’s very hard to say what it was. It felt very comfortable, like I’d known him forever. All those things, but even when you have those things you need to have other stuff too. You need to be wildly attracted, which I didn’t think I would be. It just sort of all came together. Two months is a very, very short amount of time, but I was like, “Jesus, what is he waiting for? Tick-tock, let’s get the ring.” I just knew he was the one.
And in some ways, you followed your own gut in that situation... AW: Look at you bringing it back!
You've done so much already, but are there projects you have your eyes set on doing in the future? AW: There are a lot. I’m still pitching TV shows that I’d like to write and create. I’ve always wanted to do a one-woman show similar to my book. I’ve always wanted to do a late-night talk show, but I don’t know if that would ever happen. There’s always stuff I want to do and I’m always busy trying to do them. I’m not happy if I’m not creatively fulfilled. My children can tell you, I just think like a crazy person. I like to have stuff going on, whether it’s an idea for a screenplay or a book. That gets me up in the morning.