Can We Just Leave Kristin Cavallari Alone & Let Her Date Her Younger Boyfriend?

When Kristin Cavallari went Instagram official with her new boyfriend, Mark Estes, last week, you’d think she had committed a crime with the amount of vitriol spewed at her. The offense? The Uncommon James founder is older than her new beau. She’s 37, while Estes is 24.

“Who’s that, your son?” one user commented on Cavallari’s photo with Estes.

“She’s in her cougar era!” another exclaimed.

“The midlife crisis is real ... Decided to date a 24-year-old TikToker, lmao. Yikes, gurl, how desperate can you get 😂,” said another user.

The 13-year gap between the two caused such an uproar that it made headlines from People to USA Today to TMZ. Hoda Kotb and Jenna Bush Hager even talked about it on their TV show. Ditto Chris Harrison and Lauren Zima on their podcast. It seemed everyone had a “hot take” on the former reality star’s love life — and not because she was dating someone new, but because she was dating someone younger.

I also received emails from PR companies wanting to get in on the conversation, including one with the subject line reading: “Kristin Cavallari announces new romance with 12-year age gap; relationship expert available for insights.”

“Insights?” I wondered. “Why do we need insights about a grown woman’s decision to date another consenting adult?”

I quickly fired back a response: “I’m just curious — if a celebrity man started dating someone 13 years younger, would this be in my inbox? What about Bradley Cooper’s relationship with Gigi Hadid? He’s 20 years older than her!”

I couldn’t help it. I was heated. Celebrity men have dated younger women since, well, forever, and not once have I received an email about a relationship expert’s “insights” as to why Brad Pitt is dating a jewelry designer 26 years his junior or why middle-aged Leo DiCaprio continues to date women almost exclusively under the age of 25.

As a 41-year-old single woman who’s been involved with younger men before, I found myself quick to stand up for Cavallari. I mean, it’s 2024. I can’t wrap my head around why we are still obsessed with the idea of older women dating younger men, and the amount of judgment and harassment that the woman receives (and, may I add, not the younger man) for it.

“Fundamentally, the stigmatization of older women with younger men comes from the patriarchal ideas that women after a certain (reproductive) age cannot and should not be sexual, and that sexual pleasure is a male prerogative,” Kaamna Bhojwani, a Columbia University-educated sexuality expert, tells me in an email. “But it’s not only women that this stigma limits, it’s men too. Our societies struggle with a union in which the man is not the financial provider and, in many cases, may even be the beneficiary of his older female partner; it’s a power dynamic we are just not used to. So, our inability to process and accept these relationships is layered and complex.”

Since the idea of an older woman dating a younger man is layered and complex (and might be a little difficult to digest for some), let’s break it down.

Why would an older woman be attracted to a younger man?

According to Bhojwani, older women are primarily attracted to younger men for two reasons:

1. They find them physically more attractive.

“Often men in their 50s and above don’t care much about maintaining their physical appearance, particularly if they are in a committed relationship and if they’re financially successful,” she says. “And since women have always been under pressure to maintain their looks, we have an entire generation of really fit 50+-year-old women and average-looking men their age. Did we think it wasn’t going to catch up?”

2. There’s more room for equality.

“Younger men may not feel the need or have the capacity to dominate their women, to ‘wear’ the pants, which allows more room in the relationship for transformation, exploration, and fun,” Bhojwani explains. “In many ways, the stakes are lower. Cher says one of the reasons she loves her boyfriend, who is 40 years younger than her, is that he simply ‘wasn’t afraid.’”

She adds that when it comes to an older woman being attracted to a younger man, there’s a “cheeky evolutionary twist” to consider. “An older woman with a younger man is considered unnatural because a woman is not supposed to be sexual after a certain age. But if you consider that men, on average, die seven to eight years before their partners, then women should be pairing up with younger men,” Bhojwani says. “You can’t selectively apply evolutionary theories.”

Why would a younger man be attracted to an older woman?

While it might be slightly more obvious why an older woman could be attracted to a younger man, Bhojwani says younger men are attracted to older women for “many reasons,” among the most pertinent being that they are just more sure of themselves.

“More and more, women in their 40s and 50s know who they are and are not ashamed to show it,” she explains. “This could mean emotionally, physically, and spiritually. Couple this with the ‘babygirl’ trend that is allowing men to embrace their softer, more vulnerable sides, and it would make sense that relationships in which women are the lead are more appealing to this younger generation of men.”

Not to mention, says Bhojwani, that older women today also “maintain themselves fantastically and are more confident sexually. They can often take care of themselves financially as well, which takes the pressure off a younger man.”

Why is the term “cougar” derogatory?

It should be obvious why this term is gross. While cougars, the animal, have many positive qualities — like strong, graceful, and discerning — as Bhojwani says, “The characteristic that we usually highlight most in the context of an older woman is its ability to pounce on its prey. This portrays a vision of a desperate, predatory woman and her helpless victim, which is not particularly flattering for either party involved.”

And lest we forget we live in a sexist world, Bhojwani reminds us that older men have the term “silver fox,” which “seems to communicate all the positive qualities of a fox (smooth, attractive), but none of the negative ones (untrustworthy, cunning).” Typical.

The key to whether or not the age-gap relationship is toxic or not is the power dynamic, says Bhojwani, “and it’s not always to say that the older person is the one with the control; it could be the other way around.” She continues, “We’re much more accepting of older men and younger women, despite all the Leo DiCaprio memes and jokes. The entire dialogue around older women robbing the cradle is patriarchal and misogynistic because, fundamentally, we believe that a woman who pursues her sexual pleasure after a certain age can be nothing but a social deviant.”

And we all know that’s not true. Right?!

News flash: It’s OK to be a MILF.

Cavallari is a single mom of three, which critics of her relationship with Estes love to use as ammo. “His dad would be a better daddy figure,” said one. *Cue eye roll.* Do you know his dad? Do you assume all men over the age of 40 have the emotional maturity and capacity to parent children? Because I can tell you from experience that they do not.

Like the term “cougar,” Bhojwani says it’s the value we assign to the term that makes it positive or negative.

“I’ve personally never been offended by the term MILF. I’d rather be f*ckable than not,” she shares. “If a woman is comfortable in her own skin, is able and willing to express herself, owns her sexual agency and all the facets of her femininity, then to me, that’s the most powerful thing in the world — no matter what you call it! A patriarchal mindset will always demonize a woman who owns her sexuality, especially after a certain age. It’s up to us to shed those archaic restrictive norms in favor of something more balanced, healthier, and fair to all genders.”

Research shows that older women are most satisfied dating younger men.

Despite the double standard, research shows that this arrangement can be more satisfying for women and men — both sexually and emotionally. However, Bhojwani points out that going against the societal grain and constantly having to defend yourself can take its toll.

“But I think if both parties are sure of why their relationship works, it can withstand societal opposition,” she says. “As I always counsel in my private coaching practice, sexuality and intimacy are an inside job — you have to be 100% comfortable with yourself before anything with anyone else can work. Every year, women in particular are choosing themselves and their preferences over some arbitrary standards that have been thrust on them.”

As for whether these relationships are meant to be casual or long-term, Bhojwani says, like anything in the relationship sphere, there is no definite answer.

“Can they be long-lasting? Of course they can,” she says. “It depends on the goals, compatibility, communication skills, and maturity levels of the people involved. Our cultural mindset is certainly changing to be more accepting of these relationships, and men and women can worry less about what people think and focus on the success and well-being of their relationship.”

How to approach dating a younger man as an older woman

“Be very clear about your motivations for dating a younger man. It will help you attract the right person,” Bhojwani says. She also recommends staying away from anything that perpetuates stereotypes of older women as hypersexualized, emotionally unstable, and sexually deviant, including certain dating sites. “We want to start breaking those negative associations and watch them die a natural death as more healthy examples of older women-younger men pairings emerge,” she says.

Also, “prepare for, but don’t obsess over external judgment. You may experience it. You may not. If you know why you’re doing what you’re doing and why, the rest shouldn’t matter.”

Last but not least, Bhojwani says it’s important to share your happiness. “Help others break away from senseless restrictions and embrace the true joy of connecting with one another simply as people.”

It’s like when I told my 28-year-old paramour last summer that I was 40. His response?

“So what?”