Inside Paris Jackson's Complicated Love Life

Paris Jackson has never had a "normal" life. As the second child of Michael Jackson and Debbie Rowe, "She is who my dad is," according to older brother Prince. As he told Rolling Stone in 2017, his younger sister is just like their late father "in all of her strengths," as well as in "almost all of her weaknesses." And Paris Jackson has never shied away from speaking openly about her struggles.

In June 2020, she launched a Facebook Watch series called "Unfiltered: Paris Jackson & Gabriel Glenn." Episode 2 saw her proclaim, "I have a lot of insecurities ... I'm not even close to loving myself," before sharing details on all aspects of her young life, including her numerous troubles. Following her father's death in June 2009, Paris revealed, "I gained a lot of weight, and food became an addiction." As the model and musician tried to fight it, she "fell into self-harm" and would "cut and burn" herself, before eventually attempting suicide "many times." Jackson confessed that she hoped sharing her own journey would "influence self-acceptance and courage and being comfortable in your own skin."

The series also featured Jackson speaking candidly about sexuality, love, and dating — which have led to plenty of ups and downs, too. Let's step inside Paris Jackson's complicated love life.

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ at​ 1-800-273-TALK (8255)​.

Paris Jackson got her first taste of what it means to be famous and dating at 17, when her relationship with then-18-year-old Chester Castellaw hit the spotlight in 2015. According to Us Weekly, they were first spotted together that March, before going "in a relationship" Facebook official.

Castellaw, a pro soccer player for California's Real So Cal league, was Jackson's "first true love," according to a source cited by The Washington Post, who added that he was "not only her boyfriend but also her best friend and the one person that she confides in with everything." He even received a stamp of approval from Jackson's cousin and then-co-guardian, TJ Jackson, who told ET (via Us Weekly), "No one's perfect, but he's a good boy ... He treats her well. She's happy."

Jump to October, when the young couple sparked engagement rumors by Jackson changing her last name to Castellaw on Instagram (via TMZ) ... but by December, it was all over. Radar confirmed the breakup, noting Jackson had changed her name back on Instagram while quoting an insider: "Paris broke up with Chester about three weeks ago and they are not on speaking terms right now." Although Jackson didn't address the split, she appeared to send out covert messages on Instagram, reminding "those who are going through some deep s**t right now" to "stay strong," and posting this Rune Lazuli quote: "Each tear is a poet, a healer, a teacher."

Just a few months after calling it quits with Chester Castellaw, Paris Jackson moved on to her next relationship — this time with someone older. As ET reported, she and Michael Snoddy first got together in March 2016, and by the following month, they celebrated Jackson's 18th birthday with some major PDA.

In a since-deleted post, Snoddy, a pro drummer who was 26 at the time, took to Instagram to share a snap of the couple kissing, which he captioned, "Happy birthday to one of the most incredible women I've ever met! So happy we get to celebrate YOUR DAY together!" Meanwhile, Jackson posted her own since-deleted kissing photo, writing, "Best birthday ever, my baby."

That September, the pair posed for a steamy photo shoot for Flaunt magazine, which included images of Snoddy biting Jackson's feet while they sat in a bathtub. But then, the relationship became exceptionally similar to Jackson's time with Castellaw: Engagement rumors plagued the two after Jackson was spotted wearing a diamond ring on that finger, according to the Mirror, but just like with her previous beau, they didn't make it to the one-year mark. In February 2017, Us Weekly confirmed the couple's split, with an insider telling the mag that, once again, "Paris ended things."

Paris Jackson appeared to take a break from dating (at least in the spotlight) following her 2017 split from Michael Snoddy. It wasn't until a year later that she took the world by surprise while being publicly tied to a new flame: model-actor Cara Delevingne.

According to The Sun, Delevingne and Jackson became close during Christmas 2017, after meeting at the MTV Movie Awards that May. While they never confirmed their relationship, Delevingne did invite Jackson to be her guest of honor for her Burberry X Cara holiday bash. They were later spotted holding hands in London in February 2018, and the following month, Jackson uploaded a goofy snap of her rumored girlfriend to Instagram, which she captioned, "a r t." The Daily Mail also shared photos of them smooching while out to dinner with Jackson's godfather, Macaulay Culkin.

A then-20-year-old Jackson only revealed details of their union that June, when a tabloid story alleged she was dating Delevingne, Ashley Benson, and Caroline D'Amore at the same time. Setting the record straight on Twitter, she wrote, "I've never met miss benzo. Caroline is one of my bestest friends who is **straight** and **married**, and also the mother of my godchild. Cara and I were never officially exclusive, you guys made that up." Still, when Delevingne and Benson began dating that August, Jackson appeared to fire off on Twitter, writing (via Yahoo! News), "Welp. she makes you happy so.. whatever makes you happy."

Paris Jackson hasn't shied away from openly talking about her sexuality, starting with her 2017 Rolling Stone cover story. Revealing the perks of growing up in a "very open-minded house," she recalled, "I was eight years old, in love with this female on the cover of a magazine. Instead of yelling at me, like most homophobic parents, [my dad] was making fun of me, like, 'Oh, you got yourself a girlfriend.'"

So when Digital Pride sent out a tweet in 2018 that read, "Welcome to the community, hun," Jackson fired back: "How many times have I publicly referred to the community as 'my fellow LGBTQ+'? ... I've been a part of the community for years." She also took to her Instagram Stories (via ABC News) to clarify that she actually "came out when [she] was 14," and to emphasize her dislike of labels. "I'm not 'bisexual,'" she added. "I just love people for people. I don't label myself so please don't label me. Thank you!"

In June 2020, Jackson spoke on the topic again in an episode of "Unfiltered: Paris Jackson & Gabriel Glenn": "I say I'm gay, 'cause yeah, I guess I am but ... I wouldn't consider myself bisexual, because I've dated more than just men and women." She continued, "It has nothing to do with what's in your pants. It has nothing to do with what your XY chromosome makeup is, it's literally just what are you like as a person."

Given her family legacy, it's no surprise that Paris Jackson has an affinity for music. What is surprising is that she was scared to share it with the world. Until she met Gabriel Glenn, that is. Around 2018, Jackson walked into Hollywood's Rainbow Bar & Grill, where Glenn had been playing with his band, the Trashdogs, for about a year. 

Recalling their first encounter on "Unfiltered: Paris Jackson & Gabriel Glenn," Jackson said, "Gabe had a Mötley Crüe T-shirt on and an Ohm necklace. I'm like ... wow." The attraction was mutual. "We went from the Rainbow to an afterparty and that's where I saw her playing an unplugged guitar," Glenn revealed. "It felt very intimate, and I knew that I was walking towards a head-over-heel fall."

But their attraction wasn't just physical — Glenn also inspired Jackson to unleash her creative potential. "I started writing around 13 when I bought myself a guitar, [but] I didn't really start sharing it or recording it until I met Gabriel," she told Remix in March 2020 (via People). Calling him "my muse," Jackson added, "I owe a lot to him." They've since formed their own folk band, The Soundflowers, and are pushing each other to be better every day. "Paris is the jigsaw piece that completes me as an artist," Glenn told Remix. "She creates so naturally and honestly; it inspires me to be a better songwriter."

Paris Jackson may have an estimated net worth of $100 million, but she was willing to give up all of life's luxuries to spend more time with then-boyfriend Gabriel Glenn.

"Probably one of the first things I told her [was] that I lived in a van with my dog," he explained on "Unfiltered: Paris Jackson & Gabriel Glenn," with Jackson admitting, "Within a week, I was living in his van." Jackson was aware that things were moving exceptionally fast, however, and Glenn remembered how "she kept saying to me, 'You know, when you get sick of me, just tell me to go, and I'll go.'" But that never happened. "I just ended up telling her that I didn't want her to leave," he continued. " ... I wanted to spend every day with her."

Opening up about the headline-making decision, Jackson assured, "I didn't have any problem with it whatsoever. I was happy during that time." In fact, she revealed that her father's career meant she "grew up nomadically," saying, "We were always on the move. Couch surfing, hotel hopping, always traveling." Her cousin and former guardian, TJ Jackson, also offered an explanation for the seemingly surprising move, noting it wasn't just about love: "When you grow up to be a Jackson ... there's a curiosity to what normal life is like or to what struggle is like. And she just wanted to really experience life without pillows and stuff around her."

Opening up about her sexual identity on "Unfiltered: Paris Jackson & Gabriel Glenn," Paris Jackson recalled feeling an attraction to women early on in her childhood, but admitted she "didn't know that it was a thing" and "was a little conflicted about it." Although her dad "caught on pretty quick" and was totally supportive, when she lost him in 2009, she felt forced back into the closet. 

"When he passed, I moved in with my grandmother, who's a Jehovah's Witness, and homosexuality in general is very taboo in the Black community," Jackson explained. "So that, on top of the religious aspect, it was something that I did feel like I needed to withhold for a while." After years of hiding, she spoke her truth — "The first time I came out to a family member, they didn't believe me," the model-musician revealed — and allowed herself to love anyone she wanted.

Even so, as Jackson so bluntly put it, "[I] never thought I'd end up with a dude. Thought I'd end up marrying a chick." She explained, "I've dated more women than men ... The public only knows about three long-term relationships that I've been in and they've been with men. The public doesn't know about most of the relationships I've been in." Then-boyfriend Gabriel Glenn seemed to have changed all that.

Paris Jackson hasn't had it easy. Speaking with Rolling Stone, she admitted that she was battling depression and drug addiction by age 15, and in 2013, tried to take her own life. As she explained, "It was just self-hatred, low self-esteem, thinking that I couldn't do anything right, not thinking I was worthy of living anymore."

After attempting suicide "multiple times," the model-musician sought treatment and seemed to turn things around. But in March 2019, TMZ reported that she had been hospitalized following another suicide attempt. According to sources, the heartbreaking move was reportedly a response to the sexual abuse allegations made against her father in the documentary, "Leaving Neverland."

Thankfully, she had then-boyfriend Gabriel Glenn to lean on, and when he entered Jackson's life, he "definitely scaled back the wild times," per a source cited by Radar, in order to be a worthy role model for Jackson. He also inspired her to embrace the healing power of music. "The dark parts of my mind are usually what help me write the songs I end up liking," Jackson told Remix (via People), noting that she finally had the courage to get the darkness out and onto paper. More importantly, however, he understood her. "I feel like we're the same level of damaged," she confessed on "Unfiltered: Paris Jackson & Gabriel Glenn," adding, "Gabe understands the pain I've gone through in my life and he's helped me realize this is what I was born to do."

If you or someone you know is struggling with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ at​ 1-800-273-TALK (8255)​.

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

Gabriel Glenn may have helped Paris Jackson work through her inner demons as he brought love, support, and a new musical project into her life, but their whirlwind romance wasn't meant to be. In August 2020, TMZ confirmed that the young couple had split after nearly two years of dating. According to the outlet, the pair made the decision to part ways mutually, with insiders claiming that Jackson had instead decided to focus on herself and her music and was in the studio nearly every day.

Jackson first appeared to hint at trouble in paradise during the final episode of her and Glenn's Facebook Watch series, "Unfiltered: Paris Jackson and Gabriel Glenn," which aired around the time of their breakup. Admitting that they were "constantly butting heads," she explained, "A big thing for Aries is we are very impatient, depending on what it is." Calling theirs "a very interesting dynamic," she added, "We both have double stubborn energy. I've always known I was stubborn, and I knew that he was stubborn, because he's a Taurus." Jackson also noted that Glenn was just "one of many soulmates."

For his part, Glenn also seemed to give a glimpse at a future in which he and Jackson were apart, telling viewers, "I think we said it when we first got together, even if we didn't work out as a couple, we always want to be in a band together. Our music was one thing that we wanted to hold on to no matter what."

Paris Jackson's love life remains a topic of great interest. In March 2021, actor Emile Hirsch sparked dating rumors when he posted a snap of himself hanging out with Jackson on Instagram, which he captioned with, "Hiding out with you." Followers instantly wondered if they were an item, but some fans took issue with the fact that Hirsch is 13 years older than Jackson. One user went as far as to write, per People, that "this relationship makes me uncomfortable." 

The musician wasted no time in setting the record straight while defending their friendship. Taking to the comments sections, Jackson wrote, "He's actually one of the youngest homies of mine." Explaining that "one of my best friends is in their 50s" and that she "enjoy[s] the company of people of all ages," she slammed, "You probably don't have friends older than you because elders may find you annoying or immature lol."

Jump to April, and Jackson was once again making headlines with her personal life. This time, she was linked to model Cara Delevingne (again) after Page Six spotted the pair leaving Joan Collins' Oscars 2021 afterparty together. Literary agent Alan Nevins (who co-hosted the bash) also told Page Six, "[Cara] and Paris sat together ... and they were quite stunning, I have to say." Adding fuel to the fire was an Instagram Story posted by Jackson, which revealed that she and Delevingne had gotten matching red rose tattoos, per Cosmopolitan.