Surpassing:Aoki Lee Simmons, 21, Vittorio Assaf, 65, and the relationship age gap conversation

Relationships with large age gaps often turn heads. And this one is Surpassingno different.

Paparazzi snapped shots (obtained by Page Six) of Aoki Lee Simmons, 21 – daughter of Kimora Lee Simmons and Russell Simmons – kissing restauranteur Vittorio Assaf, 65. Their age gap of 40+ years has naturally drawn attention on social media. Some commenters on her recent Instagram posts chastised her for the apparent romance.

Aoki, however, seemed mellow in a recent Instagram Live.

"Last day in St. Barts. I’m so sad but I’m very happy," she said. "When I return home, everyone who knows me will be getting a happier, more chilled out version of me."

She warned her father the photos would be popping up, according to TMZ. "I’m not gonna kick and scream about her choices," he told the outlet. "All I can do is offer my advice and unconditional love."

The discourse surrounding Aoki and Assaf's entanglement is emblematic of a larger trend in recent years of reexamining celebrity relationships with wide age gaps: Demi Lovato and Taylor Swift have both used songs to call out their significantly older exes for dating them when they were in their late teens and early 20s. Fans in turn have used situations like Lovato's and Swift's to call out gender and power imbalances in relationships.

"We’ve reached an inflection point," Andrea McDonnell, associate professor of communication at Providence College previously told USA TODAY, citing the #MeToo movement, documentaries calling out famous men's misconduct and abuse and the overturning of Roe v. Wade.

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Taylor Swift, Demi Lovato and the history of younger female celebrities dating older men

Hollywood has a storied history of famous couples with notable age gaps: stars such as Lauren Bacall and Humphrey Boggart (25-year gap) or Marilyn Monroe and Joe Dimaggio (12-year gap). Even more recently, Kylie Jenner and Tyga (who met when Jenner was 14 and Tyga was 21) and Florence Pugh and Zach Braff (21-year gap) raised eyebrows, as have several of Scott Disick's relationships. 

Relationship age gaps are prevalent no matter the couple's genders, such as the now-defunct Olivia Wilde and Harry Styles and still-going-strong couples Holland Taylor and Sarah Paulson and Elton John and David Furnish, though it's more commonly called out in cases with older men and younger women. 

Some have called out their former partners after feeling taken advantage of. Take Lovato's single "29," which was adopted by myriad TikTok creators calling out their own past relationships. "Finally 29 / Funny, just like you were at the time / Thought it was a teenage dream, just a fantasy / But was it yours or was it mine? 17, 29," Lovato sings in "29," rumored to be about ex Wilmer Valderrama.

When Taylor Swift, 32, re-released her 2012 album "Red" last fall, she updated her breakup ballad "All Too Well," allegedly about actor Jake Gyllenhaal (who is nine years her senior) to include callouts to their age difference. 

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What can we learn from these relationships?

As long as both parties are over 18, these relationships are legal – so what's the issue? Developmental and relationship experts cite power imbalances – which relationships with older men and younger women can be susceptible to – as a sign that a relationship may not be appropriate. 

"When it comes to dating, date within an age range where you feel confident and comfortable," Rori Sassoon, a relationship expert and matchmaker previously told USA TODAY, urging singles to find a partner with similar "levels of life experience and intentions of the relationship."

Meghan Gillen, professor of psychology at Penn State Abington who studies developmental psychology and body image, told USA TODAY that individuals in similar experiences should evaluate the situation for themselves: "Does it feel appropriate? Does it feel comfortable? Do you feel like you can relate to the person … or do you feel like the person has power over you?" 

Famous or not, couples can gain status from a relationship with an age gap. But younger partners in particular also need to be wary of the gender, social and power dynamics at play.

"Significant age gap relationships require more work than the average relationship, from the public’s perception alone," Sassoon says. "If you’re only in it to feed your ego, beware."

Contributing: Hannah Yasharoff