Celebrity relationships are often complicated, and when love triangles and cheating scandals mix with close personal connections, the drama becomes even more intense. Over the years, multiple stars have found themselves romantically linked with ex-partners of family members or close friends, fueling gossip and heartbreak. These entanglements reveal just how messy and unpredictable love can be in Hollywood’s spotlight.
1. Tish Cyrus – Noah Cyrus – Dominic Purcell
Tish Cyrus sparked controversy when she married actor Dominic Purcell, who had allegedly been in a “friends with benefits” relationship with her daughter, Noah Cyrus.
According to reports by People, the romance between Dominic and Noah ended shortly before Tish began dating him, causing a reported rift in the family.
When Tish and Dominic got married in 2023, Noah notably did not attend the wedding, which fueled rumors of tension.
Dominic’s relationship with both mother and daughter led to widespread speculation online, especially after fans noticed Noah’s absence from the wedding photos.
The scandal painted a complicated picture of family loyalty versus personal happiness, dividing public opinion.
Despite the whispers, Tish and Dominic have remained publicly committed since tying the knot.
2. Travis Barker – Paris Hilton – Kim Kardashian – Kourtney Kardashian
Travis Barker briefly dated Paris Hilton in 2006 but admitted in his memoir that he actually had feelings for her assistant at the time — Kim Kardashian.
He described their connection as sweet and respectful, stating they never slept together and that he wanted to be a gentleman.
Although nothing serious materialized, the short-lived relationship added to Kim’s long list of high-profile flings.
Years later, Travis began dating Kim’s sister, Kourtney Kardashian, with whom he had been longtime neighbors.
They started dating publicly in 2021 and eventually got married in 2022.
Travis addressed the past, saying Kourtney was aware of his history with Kim and that there was no ongoing drama.
The Kardashian-Barker relationship drew immense public and media attention, especially given the family ties.
Despite past links to Kim, Travis and Kourtney have cultivated a strong relationship, often sharing their love on social media.
Still, fans haven’t forgotten the tangled past between Travis and multiple Kardashians.
3. Justin Bieber – Kendall Jenner – Hailey Baldwin
Before Justin Bieber married Hailey Baldwin, he was reportedly linked to Kendall Jenner, Hailey’s best friend and a member of the Kardashian-Jenner clan.
From 2014 to 2015, dating rumors between Kendall and Justin circulated after they were seen together on several occasions.
Kendall downplayed the talk, stating he was just a family friend, but Justin hinted otherwise in interviews.
Eventually, Justin and Hailey began dating, but their first attempt ended in a dramatic fallout.
Years later, in 2018, they reunited at a Miami church event and got engaged just one month later.
Hailey credited their reconnection to their shared faith, claiming the drama had already passed.
In a 2020 Instagram Live with both women, Justin asked Kendall if she saw the engagement coming.
Kendall admitted she hadn’t, but said she hoped it would happen because she cared for them both.
Despite past entanglements, the trio seems to maintain a civil, if not close, relationship today.
4. Justin Bieber – Kourtney Kardashian – Scott Disick
In another twist, Justin Bieber was also linked to Kendall’s older sister, Kourtney Kardashian, around 2016.
Rumors suggested they were “hooking up on and off” for a few months, according to People.
Their outings together and cheeky comments only added fuel to the gossip.
The romance was kept mostly under wraps but fueled gossip given the overlapping social circles. By 2017, Kourtney chose to end her involvement with Justin to focus on her long-term partner.
Kourtney was fresh off her breakup with Scott Disick at the time, and the fling with Bieber raised eyebrows.
In 2015, Justin joked about being used by an older woman, seemingly confirming some kind of relationship.
By 2017, however, Kourtney had ended things with Justin and focused on rekindling things with Scott.
This brief relationship drew attention not only because of the age gap but also due to Bieber’s ties with the Kardashian family.
The entire saga contributed to the ever-complicated web of celebrity connections.
Though short-lived, it remains one of Justin’s most unexpected romantic chapters.
5. Demi Moore – Harry Morton – Peter Morton
Demi Moore found herself at the center of a unique triangle when she reportedly dated both Harry Morton and his father, Peter Morton.
Harry, founder of Pink Taco, dated Demi for six months in 2013 before they parted ways.
Later that same year, she was romantically linked to Peter, co-founder of the Hard Rock Café.
The 30-year age gap between Demi and Peter, along with the father-son dynamic, made headlines.
Though none of the involved parties publicly confirmed the timeline, the speculation created buzz in celebrity tabloids.
The situation raised questions about boundaries and ethics in Hollywood dating circles.
The rumored relationships showcased how tight-knit — and complicated — elite social groups can be.
While the relationships were brief, the story’s oddity continues to resurface in entertainment news.
Demi has remained quiet on the subject, preferring not to add fuel to the rumors.
6. Charli D’Amelio – Chase Hudson – Landon Barker
TikTok star Charli D’Amelio was previously in an on-and-off relationship with fellow content creator Chase Hudson.
After their final split, Charli began dating Landon Barker — who happened to be a friend of Chase and the son of Travis Barker.
The new relationship was seen by fans as a betrayal and ignited a public online feud.
Chase allegedly channeled his anger into music, releasing a song called “All the Things I Hate About You.”
The lyrics included a reference to being betrayed by a friend and labeled Charli a “homie hopper.”
This stirred up drama across TikTok and Instagram, leading to sides being taken by fans.
The D’Amelio–Hudson–Barker triangle highlighted how Gen Z celebrities experience similar scandals to their Hollywood counterparts.
Public breakups, music responses, and messy cross-friend dating continue to dominate social media trends.
Even with younger stars, the cycle of romantic overlaps and online fallout remains constant.
The situation highlights how messy love triangles have transcended traditional celebrity culture into social media, affecting young stars and their relationships publicly and painfully.
