Casey Wilson Tells Us How She Fell in Love With Her Boss and More

It’s 10:55 A.M. on a Tuesday morning, and as I’m driving around looking for a parking spot in the trendy neighborhood of Los Feliz, I spot Casey Wilson typing away on her laptop in front of Mustard Seed Cafe. She’s already ordered a tall iced coffee and looks like any other L.A. writer working on her latest script. She’s fresh-faced, gorgeous, and obviously on her game, and it feels like I’m meeting one of my Glamour colleagues instead of a much-admired Hollywood star. But that’s Casey Wilson: just like us. In fact, before we start the “on-the-record” portion of the interview, we have a full 45-minute conversation talking about personal girl stuff (that truthfully ends up being not that different from what you’ll see below). Three hours after our conversation, I walk away with not only one of my favorite interviews yet (one that has inspired me to launch Girl Talk as a permanent series) but a new friend.

Sure, it’s a lot of food, but we ordered a very healthy breakfast!

Best known as Penny Hartz on the critically beloved Happy Endings, Wilson got her start playing a student on one episode of Ed. Then in 2008, she began a two-year stint on Saturday Night Live, followed by a small role in the feature film Julie & Julia, as well as Bride Wars. A few years later, Happy Endings hit—and not only did it make her a household name, but it introduced her to her husband, David Caspe, who created the comedy. Now she’s cracking us up on Hulu’s The Hotwives of Orlando and about to star in the upcoming thriller Gone Girl with Ben Affleck. Last but not least, she stars in my favorite pilot of the upcoming fall 2014-15 season: Marry Me (which was created by her husband) on NBC. So get ready to know Casey Wilson like you never have before…

Glamour: Let’s jump right into it: What lessons have you learned about creating your own brand and being in charge of your career?

Casey Wilson: This far into the business, I am more confident with what I know or think is funny. It also comes from having a partner in comedy, which is my best friend June. With agents, I’ve learned to bring them into the process when I feel confident. You’re the only one that can really know what’s right for your career. You’re on a wing and a prayer through most of it.

Glamour: And how do you do that when you’re meeting with TV executives who can make or break a project?

Casey: A large iced coffee, followed by humor, which is the greatest equalizer. It levels any playing field. If you can have a laugh with someone, you’re then in each other’s world. Be humble and have a sense of reality. I’m in therapy, and I think everyone should be. If you have a sense of your place in the world, that’s the best preparation for anything.

It’s not all doom and gloom for Casey Wilson and Ken Marino: Their new sitcom, Marry Me, is one of the brightest spots in the fall 2014 lineup. She credits her manager, Naomi Odenkirk, with having a great eye for comedy as well.

Glamour: Your character, Annie, in Marry Me is so relatable. One of my favorite quirks about her is that she keeps getting her nails done because she thinks an engagement is coming!

Casey: My husband wrote the show and that was based on our own relationship because I kept getting my nails done over and over thinking a proposal was coming. Then the more and more you do it, you get more angry because it’s sad to get your nails done and not get proposed to! David is just so grounded and laid-back. I, on the other hand, threatened to drive my car through our house a couple weeks ago. [Laughs] I’m more emotional.

Glamour: Why is that?

Casey: I’ve had those relationships where you’re yelling at one another and you do sort of contaminate the relationship because there is no respect. David has put a very firm boundary on me. He’s like, “You may have been screaming and yelling with all your drama boyfriends, but you can’t speak to me like that.” That’s such a lesson. At the beginning of our relationship I used to fly off the handle more. I was going through this box of letters he kept of mine, and they all started with, “I’m so sorry about last night…” [Laughs] And then I did start meditating and those letters have gotten much less!

Glamour: Ken Marino plays your fiance in Marry Me. Did you have any input with casting?

Casey: I slept with Ken because I wanted to make sure the chemistry was there. A few more times, and then I was positive. [Laughs] Ken and I did a chemistry read, and David was in love with Ken from the first moment, and so was I.

Glamour: Our writer Megan Angelo pointed out that in this year’s new pilots, there’s a lot of relationships where the guy is a lot older than the girl. Ken is 45, and you’re 33. Will that come up in the show?

Casey: We’re going to play him a little younger, otherwise you have to deal with all these other issues, like ‘Are they going to have kids?” Ken looks younger than he is, but it was because he was the right guy for the part.

Glamour: In the pilot, your character tries to play it cool about a potential proposal. Did you have to play it cool with David?

Casey: I’m always the person that tries to play it cool, but [it never stays that way]. Early on in my relationship with David, Valentine’s Day came up very quick, and I was like, “I’m going to let him plan something.” But somehow I ended up renting out a theater on Wilshire Boulevard to screen Annie Hall. [Laughs] So I can’t speak to playing it cool. I don’t want to say I was more into David than he was into me, but we had been working together for about a year before we started dating. I really liked him, but there was nothing I could do, which is really hard for women, especially because we want to make things happen.

Glamour: So what changed?

Casey: I ultimately started dating other people, but not to [make him jealous]. I actually had to go to that darker place of, “I don’t think this is going to happen.” I started dating other people just to get out there. I think it bothered him, though he said it didn’t. His sister said to him, “You know she’s going to date other people,” so then he was like, “OK, let’s give this a try.” But it was such a different thing coming as his idea in a way, rather than me forcing it. I think that’s true of work stuff also. Just forcing anything has never worked. I still try to do that though!

Wilson with her hubby, David Caspe.

Glamour: How did David propose?

Casey: He bought a house the year before, and that was awkward because I was happy for him, but I wasn’t going to be like, “Oh, I’m moving into this house. It’s going to be a nice house for you… and me, and our children one day.” He did eventually ask me to move in, but I said I didn’t want to move in until we were engaged. Otherwise I could see me moving in, and then six years could go by and we’d be living together. I’d already lived with a couple guys. Plus, I really loved my place and living alone. So David renovated the house for a year, and the night that he slept over there for the first time, I came over, [with my] nails done, and self-applied makeup because he’s a horrible actor [and I knew something was coming]. He proposed to me that first night in the new house. Then he flew my dad and brother out, and his parents walked up the driveway and everyone came over. My best friends were there too, and caterers came in and set up a full meal and champagne, and it was just a beautiful dinner together in the house.

Glamour: Did your costars on Happy Endings pick up on what was going on?

Casey: They did, but they were all really sweet about it. Adam Pally did a speech at our wedding that was really funny. He said very sarcastically to all the guests, “Yeah, we all thought this would be a great idea!” But everybody was really nice and cool about it.

Wilson and Adam Pally remain best friends even post-Happy Endings.

Glamour: For those of us in our thirties who haven’t found the right guy yet, what’s your best advice?

Casey: Ask your girlfriends or just people you meet to set you up. I did that, and I tell my girlfriends to do it. Maybe that’s simple advice, but just put it out there and tell people you’re interested.

Glamour: OK, do you have anyone for me? [Laughs]

Casey: Ha! I’m a huge matchmaker. I’ve had a marriage and a divorce with the same two, so I can’t really take it as a win, but I can get you guys together and then you’re on your own! Also, here’s another piece of advice: Don’t get down on your luck because you haven’t met the right guy yet. People are attracted to a happy energy, and it’s important you keep that going. It’s the same with careers too. If you think it won’t happen, there’s a greater chance it won’t.

Glamour: What’s funny is that you told yourself you didn’t think things would work out with you and David in the beginning.

Casey: True, but there’s a difference between releasing something in your head and saying, “I’m done, but I’m open to other things,” versus “This is never going to happen.” I think it’s really hard not to get dark because everyone wants to meet someone. And go online too! I would do that 100 percent.

Glamour: We have to talk about the fact that you told John Stamos how you lost your virginity on the Yahoo! series Losing It With John Stamos. You essentially talked to Uncle Jesse about your sex life!

Casey: He’s a doll. I haven’t been able to bring myself to watch it though because it was just such a crazy day, but he’s just so genuinely sweet. He was so invested in what I was telling him, and I just kept telling him! I get excited thinking about him. [Laughs]

Glamour: You admitted to him that you had to go to therapy because of how emotional your breakup with your boyfriend was. If you have a daughter one day, what advice will you give her?

Casey: The first thing I’ll do is show her Losing It With John Stamos. [Laughs] I don’t know how my parents handled such an emotional human being. My goal is to just process things with more stability, so hopefully I can just listen and provide some sort of voice. Things seem so big when you’re younger, and I hope my daughter doesn’t get so caught up in those moments. If nothing else, you can always tell it to John Stamos.

Have mercy! Wilson on Losing It With John Stamos.

Glamour: Let’s talk health and fitness. What’s your best advice for maintaining a healthy lifestyle?

Casey: I love working out actually. I used to hate it. I like being in a class because I know I’m not going to just stop. Otherwise I would read a Glamour magazine and walk very slowly on the treadmill, which is great too of course!

Glamour: Being in the public eye, how do you deal with the constant pressure to always look your best?

Casey: Well, I obviously haven’t succumbed to it! To be honest, I wish I cared more. I don’t seem to have that chip. It has kind of hurt me in the business a little bit. In some ways, in this business, you give yourself more protection by being thinner—like you’re more exposed to just look normal, and in some ways, it would be easier for me. At the same time, I was laughing when my wedding was coming up, thinking, “I should really look my best for the wedding.” I cared more about that, which was only 150 people, than when millions watch you on TV, which is funny. So that’s when I stepped it up. I’ve always really loved life. Vanity is part of the business, but there’s only so far I’m willing to go.

Glamour: I just want our readers to know how gorgeous you are. There’s nothing to change.

Casey: Well, thank you. That’s very kind of you to say.__

Just to prove how bad (or good!) her handwriting is, I made Casey sign an autograph (yearbook-style) for us. It reads: “Glamour, I had a ball getting lunch! Keep in touch see you next year! Love, love, love, Casey Wilson. *This is my handwriting on its best behavior!!”

Glamour: If I was raiding your vanity, what are the makeup and hair products you can’t live without?

Casey: I love Stila convertible color that you can use on your cheeks and lips. For my hair, I use It’s a 10. It’s a leave-in condition, and I love it. My hair is so thick, and it makes it look amazing.

Glamour: Stress: how do you handle it?

Casey: Meditation in the morning and a drink at night! That’s a Glamour Do and Don’t right there. [Laughs]

Marry Me premieres October 14 on NBC.

__What’s your favorite piece of advice from Casey? Also, who would you like me to interview next for Girl Talk With…?