Reese Witherspoon’s Daughter Ava Recreates Iconic Cruel Intentions Look With Boyfriend on TikTok

Ava Phillippe, the daughter of Reese Witherspoon and Ryan Phillippe, surprised fans when she and her boyfriend, Dakota Brubaker, recreated a memorable look from the film Cruel Intentions on TikTok after being compared to her famous parents. This playful homage has sparked renewed interest in how closely Ava and Dakota resemble Reese and Ryan, drawing attention to Ava’s creative nods to her family’s Hollywood legacy.

A TikTok Tribute Mirrors a Hollywood Couple from the 1990s

Social media attention turned to Ava Phillippe and Dakota Brubaker after a fan commented on their resemblance to Reese Witherspoon and Ryan Phillippe, referencing their iconic appearance in the 1999 film Cruel Intentions. Ava and Dakota playfully accepted the comparison by staging a TikTok video, with Ava dressed casually in a white T-shirt and jeans, visibly awkward as the clip began. Dakota entered the frame styled with blonde curls, a black turtleneck, and glasses, closely mirroring Ryan Phillippe’s look from the film. To heighten the similarity, Ava used The Verve’s “Bittersweet Symphony” as the soundtrack, echoing the film’s memorable mood.

The TikTok post included a comment echoing fans’ amusement:

“Close enough. Welcome back Reese & Ryan!”

fan comment

Reese and Ryan: The Original Inspiration

For context, Reese Witherspoon and Ryan Phillippe were not only co-stars in Cruel Intentions but also a real-life couple at the time, dating since 1997 before marrying in 1999—the same year the film and Ava’s birth took place. Their relationship was heavily covered in the late 1990s and early 2000s, ending in 2006. The visual homage in the TikTok nods to both the film’s cult status and Reese and Ryan’s place as a celebrated Hollywood duo of that era.

Reese Witherspoon
Image of: Reese Witherspoon

Ava’s Social Media References to Iconic Roles

Ava Phillippe has shown a consistent sense of humor and awareness about her family’s acting legacy by integrating references into her own online presence. Beyond the Cruel Intentions video, Ava often winks at her mother’s filmography. She recently participated in the “holy airball” trend on TikTok by referencing Reese’s role as Elle Woods in Legally Blonde, an iconic role from the early 2000s. Earlier in the spring, Ava appeared as a cameo in Netflix’s Ransom Canyon, embracing a ‘90s aesthetic and returning to blonde hair—a direct homage to her mother’s look during those years. She also shared photos in a pink bikini reminiscent of Elle Woods’ application video at Harvard, further strengthening her connection to Reese’s memorable characters.

Reactions to the Comparisons

In the TikTok clip, at its conclusion, Ava and Dakota both humorously shook their heads and mouthed “no,” signaling that, although the comparisons may feel unusual, both take it in stride with good humor and a hint of playful discomfort. The couple’s willingness to lean into these references reflects the intense attention and sometimes mixed emotions that come with being the children of Hollywood icons.

Family Moments and Enduring Legacy

While fun social media posts give fans a glimpse of the next generation, Ava also commemorates more personal moments. She has previously shared touching family tributes, like posting throwback photos of her mother for Reese’s birthday. These gestures underline not just Ava’s resemblance to her mother and her parents’ impact on pop culture, but also their ongoing presence in her life as she navigates both public and private spheres.

As fans continue to notice and comment on the similarities between Ava Phillippe, Dakota Brubaker, and the famous Witherspoon-Phillippe duo, Ava’s responses highlight both the weight of her Hollywood heritage and her ability to balance nostalgia, humor, and individuality on platforms like TikTok. Whether referencing Cruel Intentions or Legally Blonde, her tributes serve as reminders of Reese Witherspoon’s iconic roles and the enduring fascination with Hollywood families.