Ishaan Khatter Unfiltered: On Dating, Male Friends & Mental Health

Ishaan Khatter Unfiltered: On Dating, Male Friends & Mental Health

Ishaan Khatter challenged me, surprised me and honestly made me emotional. He dropped bars and extreme honesty! What struck me most about Ishaan is how intentional he is with his friendships. The man people see as confident is also the friend who checks in just because. Who pushes the men around him to talk instead of shutting down. Who sends voice notes saying, “I hope you’re okay,” without realizing how rare that is. Because to him, it isn’t. He’s also spent his career refusing to be reduced to the “token” role the industry had ready for someone who looks like him. Instead of chasing the obvious path, he’s been quietly building a body of work and a sense of self on his own terms. But underneath that is something more complicated. Ishaan opened up about growing up surrounded by strong women and watching his mother sacrifice her own creative dreams to hold everything together. And then he said something I haven’t stopped thinking about: “Men aren’t raised to be men. They’re raised not to be women.” And that one shift — from raising boys away from something to raising them toward something — might change everything. This episode of Shame Less with Lilly Singh is presented by my charity, Unicorn Island Fund.

Shefali Shah's Most Honest Interview: On Marriage, Rumours & Motherhood

Quite possibly one of the most HONEST people I've ever met, Shefali Shah had my jaw on the ground so many times throughout this interview. Shefali has built her career refusing to be background in someone else’s story. She’s turned down roles that reduce women to relationships and has always pushed one question to the front: who is she, beyond who she belongs to? In doing that, she’s quietly been giving women permission to step outside the expectations written for them. Here’s what struck me about Shefali. The woman who is unapologetic on screen used to tie her self-worth to whether she landed a lead role or not. The woman who prioritizes her relationships with her girlfriends once didn't set boundaries for herself.  The woman who tells others not to rush into marriage worked hard at being the perfect good girl so she could one day be the perfect good wife. That’s not a contradiction. That’s what it looks like to unlearn the rules you were raised with. Messy. Non-linear. Honest. And in that honesty, she creates space for other women to do the same... to question, to push back, to not meet every expectation placed on them. She said something I keep coming back to: we teach women to be defined by their roles... wife, mother, daughter. But the moment you see yourself only through those labels, you stop asking the most important question. Not what do I owe everyone else, but who am I when no one is watching? This episode of Shame Less With Lilly Singh is presented by my charity, Unicorn Island Fund.

Anil Kapoor on Being the OG Girl Dad and the Pressure to Provide

I sat down with Anil Kapoor and I wasn't expecting it to go this deep.    We started talking about what it was like growing up, watching his dad get let down by an industry that once celebrated him and then didn’t. That moment stayed with him. It shaped his drive, his sense of responsibility, and the pressure he carried... not just to succeed, but to provide for everyone around him.   Then we got into his daughters... two of the most fearless, outspoken women in Indian cinema today. He brushed off any credit. But as we kept talking, a pattern emerged: every answer pointed to someone else. His dad. His wife. His kids. Never himself.   So I called it out.   What followed was one of the most honest conversations I’ve had on this show... about being a girl dad before it had a name, the tension between providing and being present, and what it costs to give everything to everyone without ever asking what you want in return.   This episode of Shame Less with Lilly Singh is presented by my charity, Unicorn Island Fund.

Kajol on Internet Culture, Gen Z and Parenting Hacks

There’s a version of Kajol the world knows: iconic films, unforgettable characters, timeless moments. This conversation is not just that. When Kajol sat down with me, she was completely unapologetic. We talked about starting in the industry at 16 with no plan, the difference between her generation and Gen Z and why too much information might be making it harder to know what you want.   Now raising kids in a completely different world, she opened up about parenting a Gen Z daughter, the pressure young girls face today and how motherhood forced her to learn one of the hardest lessons: to stop talking and start listening.   We also revisited some of the most iconic films like Dilwale Dulhania Le Jayenge, Kuch Kuch Hota Hai and Kabhi Khushi Kabhie Gham... and let me tell you, she did not hold back. From laughing through emotional scenes to unpacking complicated family dynamics, to admitting what she’d actually change if those scenes were shot today… we got into all of it.   If you grew up watching her, this will hit you in a completely different way.   This episode of Shame Less with Lilly Singh is presented by my charity, Unicorn Island Fund.

Nora Fatehi on the Success Mindset Behind Her Rise

There's a version of Nora Fatehi the internet has decided on. This conversation is not that. When we sit down for these conversations at Shame Less, we always expect honesty — but when Nora sat down with us, she gave us everything, and we mean EVERYTHING. We talked about growing up in Toronto, feeling pulled toward India with no connections and no plan, and how she didn't just show up and hope for the best — she studied, she strategized, and she outworked everyone in a room that wasn't built for her. She got into what growing up without her father did to how she loves, what feminism actually means to her beyond the headlines, and what she really thinks about men. All of it, unfiltered. If you think you know her, watch this. You don't. Filmed: November 2025.