Ahead of her visit to NZ in July for her Little Big Bitch tour, Chelsea Handler talks to Alice O’Connell about everything being high as a kite when meeting a former US president, to being proudly childfree, to working out what brings her joy – and might just bring you joy.
It’s pretty rare that you talk to a woman who tells it to you so straight. But Chelsea Handler truly is one of a kind.
In our short 15-minute Zoom chat (where she wore no make-up, a grey beanie and sweatshirt, while sitting in front of a snowy window in her Canadian holiday home) we talk about accidentally doing drugs before playing pickleball with a former US President, the joy of knowing what she wants, having her shit together in her 50th year, not taking shit from anyone else and her love of the sisterhood.
She’s found time today for a few interviews amongst her busy schedule – touring her stand-up show internationally, her podcast (a weekly advice show called Dear Chelsea) and her books (she has six best-selling titles and has another in the works).
Chelsea says she knew exactly what she wanted her life to look like when she was just a little girl – it was a big life. A life where she would be rich, travel the world and be very happy. She also knew that life would not be one that included a husband, or children. Those, she says, she always felt were a “buzzkill”.
She knows what makes her happy, and she wants that for other women, whether that includes a husband and children, or not. She just hopes that we know what it is that brings us joy.
She’s hoping to spread some of that joy at her upcoming NZ shows (she’s in Auckland and Wellington this July), as part of her wildly successful Little Big Bitch Tour.
“You can expect all sorts of business from me – my childhood stories, my adult stories, famous people’s stories, men who have been cancelled stories, lot of drugs. I love talking about drugs. They’re my favourite topic,” she says.
Here’s some of the highlights from our chat.
On Being A “Magnet for Drama”
Anywhere she goes, Chelsea says she winds up getting into some kind of drama – likely down to the fact that she’s pretty open to things happening aaaand, her fondness of drama.
“Oh yeah, I’m a magnet for drama, and for ridiculousness,” she says. “My brothers and sisters are like, every time we go on vacation, I’ve always got something going on. There’s gonna be a good story. Like last time, we were in Maine together and we ended up with George W. Bush’s at his compound Kennebunkport.
“I had three edibles and he was showing me his art collection, with my sunglasses on because I was too high to take them off and look him in the eyes. I said, ‘Mr. President, you need to know something: I am as high as a kite right now.’ And as my brother walked out he goes, ‘God, you know, every time we go on vacation with you something ridiculous like this happens. We just played pickleball at Kennebunkport!’”
On Just Turning 49 and Looking Ahead to 50
How is Chelsea feeling about turning the big 5-0 in 2025? Pretty darn fabulous, that’s how.
“I mean, well, I’m pretty excited that I’m such a cutie patootie at 50,” she says. “I’m 50 years old?! Like whoa! I thought 50 wasn’t going to be this much fun. I thought it was old before, but now I don’t care.”
On Choosing to Be Single & Childfree
One of the topics Chelsea loves to talk about (besides drugs, of course) is her choice to be single and childfree. Given it’s such a valid life choice for men AND women, she wishes it was something we talk about more often and openly.
For Chelsea, she always knew that she was going to live a big fun life, and that life would not include a husband or children.
“I always just wanted to have a great big fun life!” she says. “I want to travel the world!”
“I wrote this letter to myself, like when I was a little girl, about what I thought I could be – the woman I would become, you know? I just wanted to fast forward through childhood and become the woman. I had this woman in my mind and now I’m here and I am this woman!”
“I’m so happy that I know myself so well that I knew enough to not have children and that I can I have tons of children in my life, but I don’t want to be a parent. That’s a buzzkill for me – like, that doesn’t sound fun for me. And I don’t want to be married either. I want to have lots of lovers and different men all over the world and have fun with them. And that’s exciting to me. Marriage to me seems like the party’s over.”
“And so I have just a different way of looking at things. And I always have the confidence about my own opinion. I know who I am. So I’m not worried that I’m like making the wrong decision. I’m like, ‘Oh good for you for knowing your truth.’ And I think women also should get a lot more credit for knowing that they are not cut out to be parents instead of just becoming a shitty one.”
On Finding Joy and Working Out What Makes YOU Happiest
Is there a recipe to finding happiness? Chelsea certainly thinks so.
“First you have to spend time alone,” she says. “Like, you have to really understand who you are and who are you when you’re alone with your own thoughts. Then you’re not relying on other people to distract you – you’re getting real with yourself, you have to understand what you love, not what someone else loves.”
“Like, I love skiing. And so I spent so much time getting good at it because I just wanted to be an amazing skier. And I am now! I could ski pretty much anything. I’m better than like, so many of the people that I know that used to be good skiers, because I made the time and the effort to get so good at something and it brings me so much joy.”
“But like I had to really get real with myself to discover that. What brings you joy could be anything – it could be planting flowers or reading books – I mean, that brings me a lot of joy too, I love smoking pot, reading books and going skiing. Those are like my three passions. Right? Now and love that I’m having a blast doing it. You know, it’s just like I don’t apologize or explain myself to anyone. That’s what I love.”
On Being the Woman to Go To For Advice
Chelsea is the woman that a lot of people would love to go have a few margaritas with (particularly if it was alongside one of her closest friends, Jennifer Aniston too), but beyond being someone who would be a lot of fun to hang out with – she’s also someone a lot of women now look up to for advice. That ‘tell it straight’ mentality she has, and the fact she’s had a lot of life experience that she’s not afraid to talk about, has shaped her as a go-to woman for sound advice. She’s even turned it into a wildly successful podcast, Dear Chelsea, where people call in each week and – often with the help of a celebrity guest – she tackles their current problem or situation.
She says this has all come about because she loves the sisterhood – and, she knows what she’s talking about. “I have my shit together!” she says.
“I mean, I’m always a sister, too,” she says. “I try to be a sister to everyone and to be cool and honest with people and kind of give them a push in the right direction. You know, you want everybody to win, not just you. You want to be like spread the joy and sunshine! I’ll be your friend and I’ll help you, you know, get through tough times!”
“ I think just from experiencing that and being that kind of girl – I have two sisters so I know how to be a sister. My podcast is all about people calling in for life advice, which was kind of started as a joke and tongue in cheek and became like a real thing. But sometimes you do need an opinion from someone who doesn’t know about your life personally, like you need a fresh set of ears. And so I like to do that for everybody! Anyone I can help, I will.”
“And, you know, I do give good advice because I have my shit together. I’m not scared of things, like, I’m willing and able to make a fool out of myself and embarrass myself. I’m willing to try things that I don’t feel comfortable doing – other than dancing, that is. I can’t really dance. I have no rhythm and it’s not a cute look.”
On Whether Women Can Really “Have it All”
“Well, it depends what you think all is like,” says Chelsea. “To me all is not having children, not being tethered to anyone and having the freedom to be me. Having it all is having your freedom to do whatever you want, whenever you want and operate with you know integrity, which frees you up even more.”
“I think having it all is so different for everyone else. And first of all, you have to start by being grateful for what you do have, instead of thinking. ‘like, where am I’m going?! Is this where I’m headed?! What’s everyone else doing?! Just like, enjoy what’s happening! It’s usually the best way for success to come to you more easily is when you’re really focused and present on what’s happening right now.”
Chelsea is in New Zealand for her Little Big Bitch Tour in July 2024. Tickets are available now.
