Amanda Goh

Chelsea Handler says her dating life changed after 40: ‘I’m too hot to be dating 65-year-olds’

Chelsea Handler, 51, isn’t sticking to traditional dating expectations, especially when it comes to age.

On Thursday’s episode of the “IRL podcast,” the comedian spoke about dating and the reason she doesn’t want to build her life around a partner.

Handler told host Angie Martinez that she’s seeing a man 14 years her junior, whom she met at a casino in Las Vegas. When asked about their age gap, Handler said she doesn’t “really feel anything” about it, but added that she initially wasn’t looking to date someone younger.

“When I was young, 20s, 30s, I always dated older guys. 20s, like 20 years older than me. I always dated 40-year-olds when I was 20, 50-year-olds when I was 30,” Handler said.

But when she turned 40, she began rethinking that pattern, and decided she didn’t want to date 60-year-olds.

“Like, I’ve got to flip it and reverse it, you know? So, now I’m heading in the opposite direction because I’m too hot to be dating a 65-year-old. Let’s be honest,” Handler said. “I mean, I don’t work this hard on myself and take such good care of myself so that I can’t have fun and, you know, have a good time.”

She added that once she got to know the man she’s been seeing better, that “age thing went out the window.”

Still, Handler said she values her independence.

“I like traveling a lot. I like hooking up with guys. I don’t like to get too serious. I don’t want someone in my space all the time,” she said.

She added that her “whole vibe” is about freedom. Even though she sees marriage as “outdated,” Handler said she’d do it for the irony.

“But, you know, since I’ve bemoaned marriage my whole entire public life, I would be really hypocritical for me to get married, which means I’ll probably do it,” Handler said.

Handler has long been candid about her approach to dating.

During an appearance on “Call Her Daddy” in February 2025, Handler said she prefers to live life on her own terms.

“I’m not interested in long-term commitments, to work, to people, to anything. I am a free spirit and I want to remain and soar like an eagle,” she told host Alex Cooper.

She isn’t the only Hollywood star who has embraced relationships with younger partners.

In 2024, Cher said she prefers to date younger men because older ones are often intimidated by her. The singer has a 40-year age gap with her boyfriend, Alexander Edwards.

In 2025, Tracee Ellis Ross said she dates younger men because men her age are often “steeped in toxic masculinity.

“And anything that starts to smell of that for me — I did enough of it where I was controlled and felt like I was a possession or a prize — I just have no interest in it. And I will not do it again,” Ross said.




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I moved in with my girlfriend in London after only a few months of dating. I was terrified.

I met an incredible woman on a random outing to London while I was living life in slow motion, alone in a quiet English seaside town.

I fell in love in a way that surprised me, both in its speed and its certainty. I knew it was her. The relationship unfolded across train rides, weekends, and the growing realization that what I thought was a temporary chapter in my life was quietly becoming its center.

After a few months together, a practical question emerged. Our rent contracts were ending. Suddenly, there was an opportunity to do something that felt both thrilling and reckless: move in together and move back to London after years in a small town.

It felt risky, especially after years of living alone and so soon after meeting. But it also felt like an invitation to fully embrace a new chapter abroad, without half-measures.

I wasn’t sure I knew how to share my space with a partner

My fear wasn’t about commitment in the abstract. It was far more mundane and, in some ways, more unsettling: I didn’t know if I actually knew how to live with someone.

I had lived with my parents and sisters in Mexico, and I also had roommates during my student exchange in Spain, but that was a long time ago. Ever since leaving my country to see what life had to offer, I had lived entirely on my own.

Living alone abroad had sharpened my sense of independence. I had my routines, my rhythms, and my silence. Sharing a space meant renegotiating all of that in a city as intense as London — while also being a foreigner still figuring out where I belonged, and doing it with someone I was still getting to know.

I worried about losing the version of myself I had worked hard to build over the past two years. I worried about friction, mismatched habits, and what happens when two people bring different expectations into the same kitchen, the same mornings, and the same tired evenings.

Staying separate felt equally wrong, though. At some point, I had to give it a real chance.

I was also afraid we’d lose the magic

Once we made the decision, another fear surfaced, one I hadn’t said out loud at first. I worried that moving in together would flatten the magic of the relationship.

Dating, especially in the early stages, allows for a certain level of curation. You see each other rested, excited, and intentional. Living together removes that buffer almost immediately. There are no intermissions, no reset between interactions.

I worried the romance would dissolve into logistics. That excitement would be replaced by grocery lists, chores, and bad habits. What if the softness of the early months would harden under the weight of constant proximity?

It felt like skipping too far ahead in the story. I wondered if we were rushing something that deserved more time to breathe. What if she realized I wasn’t what she hoped for? What if our energies didn’t align? What if it was simply too much?

But I learned that the honeymoon phase doesn’t end because of shared space. It ends when curiosity stops. Living together, as it turned out, demanded more curiosity, not less.

Moving transformed the relationship

The shift was immediate, but not in the way I expected. Living together didn’t make things smaller. It made them deeper.

We learned from each other in unglamorous but essential ways: how we start our mornings, how we decompress after long days, and how we navigate stress without turning it into conflict. The relationship became less performative and more real.

Living with my girlfriend allowed me to truly know her, not just the version of her that appears on dates. I saw her patience, her habits, her quiet moments, and her resilience. I learned how she shows care when no one is watching.

In that process, I also learned more about myself. I realized that independence doesn’t disappear when you share a life with someone. It evolves. Living together abroad didn’t shrink my world; it expanded it.

I’ve lived in many places and many houses, but this is the first time I can say that, with her, it feels like home.




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Read the pitch decks of 14 startups looking to disrupt dating apps and social networking that have raised millions

A new generation of consumer social startups is emerging.

From platforms focused on getting people to meet IRL to dating apps taking on Tinder or Hinge, startups are disrupting the digital social scene.

Founders of these startups are tackling problems like loneliness, dating app fatigue, and general dissatisfaction with the current social media incumbents.

Some founders come from Big Tech backgrounds, like the Instagram-heavy team behind photo-sharing app Retro, or the ex-Google employees building the social-mapping app PamPam. Gen Z founders are also throwing their hats in the ring, like Isabella Epstein’s IRL-focused app Kndrd, or Tiffany “TZ” Zhong’s Noplace app.

Investors are taking notice.

For instance, the IRL-social app 222, which matches strangers over dinner or activities with a personality quiz, raised a $2.5 million seed round from venture capital firms like 1517 Fund, General Catalyst, and Best Nights VC in 2024.

“We’re entering this new wave of social where people are trying to revert back to what people really use these platforms for to begin with — which is connection,” Maitree Mervana Parekh, a principal at Acrew Capital, told Business Insider in 2024.

Meet 19 startups in social networking, dating, and AI that investors have their eyes on

Some venture capital funds — such as French firm Intuition VC or gaming-focused firm Patron — have made tackling loneliness and relationships part of their investment theses.

But it’s not just friendship and dating that are ripe for disruption.

Startups like Khosla Ventures-backed Gigi, Yale-student-founded Series, Boardy, Filament, and Goodword have raised capital for AI tools to help people network better or maintain professional relationships.

“When people think about loneliness, they think about friends and family,” Goodword CEO Caroline Dell recently told Business Insider. “But we spend most of our waking hours at work as professionals.”

Meet the founders of 11 startups competing with dating app giants like Tinder

Other startups, like Diem and Spill, have opened up investment rounds to include users themselves using the platform Wefunder.

It’s not yet clear how many of these investments will pan out. Some startups are pre-revenue, while others are experimenting with monetization methods (such as freemium models).

“Founders have to be honest with themselves,” said Marlon Nichols, a founding partner at Mac Venture Capital. “Some of them aren’t really venture-scale or venture-type investments. We’re looking for the next big thing, the next category leader.”

Meet 12 VCs and investors eyeing new social startups

Business Insider spoke with several social media and dating app founders about how they are raising capital, including the pitch decks they used to raise millions of dollars.

Read the pitch decks that helped 14 social-networking and dating startups raise millions of dollars:

Note: Pitch decks are sorted by investment stage and size of round.

Series A

Seed

Pre-Seed

Other

Read about more social networking and dating startups raising millions:

  • Airbuds, a social music app, told Business Insider in November that it has raised $10.2 million — including a recent check from Alexis Ohanian’s VC fund.
  • Sweatpals, a fitness and wellness social platform, raised $12 million in seed funding.
  • Sitch, an AI matchmaking dating app, announced in April that it had raised $2 million in pre-seed funding.
  • Amata, another AI matchmaking dating startup, recently launched in the US and disclosed that it raised $6 million in 2023.
  • Gigi, an AI social network for making professional connections, announced in September that it raised $3 million from Khosla Ventures.
  • Corner, a social mapping app for Gen Z, disclosed in September that it has raised $3.75 million.




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Dating after your partner dies is hard. I feel guilty for wanting connection, but I also need it.

Dating is difficult at any age. Dating when you have a child is complicated. But, when you decide to date after the passing of your partner, there’s even more to consider. I was 48 when my husband succumbed to cancer. My daughter was almost 10.

Why would I want to date? I was heartbroken. A piece of my life and my entire vision of the future had been ripped away from me. I didn’t want love. I wasn’t interested in a replacement. I’d lost the illusion of forever.

I just wanted conversation, companionship, and a new way of looking forward and reimagining. But, any kind of reimagining requires imagination and reconciliation. I was parenting a traumatized child while also trying to care for myself.

What would my daughter think about me dating? Would she think I was betraying her dad?

I didn’t tell my daughter I was going on dates at first. I didn’t bring anyone to meet her until I’d had a few positive dates. I didn’t introduce her to anyone I didn’t think of as potential friend, a good person.

I was clear with everyone I went out with that I wasn’t looking for something permanent and that I certainly wasn’t looking for a new dad for my daughter. My daughter adored her dad, and rightfully so. She had thoughts on the few people I did introduce her to:

“He’s too young for you.”

“He likes you too much.”

“I don’t have a good feeling about him. Even if he got me a good present.”

And, eventually, “He seems pretty chill.”

Then, when you find someone you’re interested in seeing, there’s the challenge of when and where

Solo parenting is not single parenting. My daughter didn’t split time between me and another parent. I couldn’t tell a potential date, “my daughter’s with her other parent this weekend — I’m free.”

I had to define what my boundaries were and enforce them. So, no one could be in the space I shared with my daughter. I couldn’t make him dinner, invite him in for drinks.

There’s also not a lot of free time for a solo parent with a full-time job. I needed to be there for soccer, Girl Scouts, school plays. Those were nonnegotiable. I wouldn’t date someone who wanted me to prioritize them over my daughter.

There were also internal challenges I had to settle for myself

Dating as a widowed parent means accepting a need for connection and feeling guilty for wanting it at the same time.

What did it say about me? Did it mean that my feelings about my husband hadn’t been sincere? Was it fair to the men I went out with?

I wanted conversation with people who didn’t know me in my married life, people who could see present and future me, but who also wouldn’t push too much for a future with me.

Even with so much to consider, dating has not only been possible, but it’s been positive

Despite all of the challenges, I’m not only making it work, I’m thriving. I’ve met some really good people who want connection, whatever that looks like, in this iteration of our lives.




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