Demi Lovato’s Dating History: The Big and Small Romances on Her Way to Getting Engaged to Max Ehrich

Why stand still when you’re ready to move forward?

Demi Lovato announced last week that she was engaged to Max Ehrich, a 10-carat culmination of their whirlwind romance that began in as early as March.  

Not that it was a whirlwind courtship for Ehrich, who had his eye on the Sonny With a Chance star almost a decade ago.

“All I wanted for Christmas was Demi Lovato,” the actor tweeted back in 2011. “#CantAlwaysGetWhatYouWant.”

But if you wait sometimes… you might!

So, just months after making a love connection with Lovato in real life, Ehrich got down on one knee on the beach at sunset and popped the question.

“@maxehrich—I knew I loved you the moment I met you. It was something I can’t describe to anyone who hasn’t experienced it firsthand but luckily you did too,” Lovato wrote on Instagram on July 22. “I’ve never felt so unconditionally loved by someone in my life (other than my parents) flaws and all. You never pressure me to be anything other than myself. And you make me want to be the best version of myself.

“I’m honored to accept your hand in marriage. I love you more than a caption could express but I’m ecstatic to start a family and life with you. I love you forever my baby. My partner. Here’s to our future!!!!”

Sometimes it can be hard to distance 15-year-old Lovato who got her big break on the Disney Channel from the 27-year-old woman she is today. But As the Bell Rings and Camp Rock are in the distant past. Wedding bells and a hulking rock on her finger are what’s up right now.

Before a certain Disney-fueled entanglement captured the headlines, another famous brother was sliding into Demi’s DMs.

In 2009, Miley Cyrus‘ big brother Trace, 20, publicly flirted with a 16-year-old Demi—and vice versa—for two months on Twitter, throwing out tentative plans to see everything from The Twilight Saga: New Moon to the Eiffel Tower together. And that July they did finally spend some real face time together in Los Angeles, even catching a movie (alas, the less romantic Transformers) before Trace left to go on tour.

It was all over just days later, though, when Demi tweeted, “Now listen I think you and me have come to the end of our time.. What’d ya want some kind of reaction? Well, okay that’s fine.” Then it got a little complicated, with Trace posting a pic of his ex Hanna Beth, noting that the snap had been his phone background all along…

The Twitterverse’s reaction eventually prompted Trace to conclude, “I just got really confused… Is it possible to breakup when you were never together with someone and only friends? Hmm this is new to me.”

Demi then finished that chapter off for good with a reminder that her album Here We Go Again was dropping in two days. ‘Nuff said.

The Camp Rock co-stars were too cute together after Demi scored the role of Mitchie Torres in the 2008 Disney Channel movie and its sequel, Camp Rock 2: The Final Jam. She and Joe recorded songs such as “This Is Me” and “Make a Wave” together, so joining the Jonas Brothers‘ world tour in 2010 was a no-brainer. 

But Joe and Demi split up in 2010 and decided to just be friends.

To clear up the speculation that Joe hadn’t gone about splitting up in the most gracious of ways, Demi tweeted that May, “There are so many crazy rumors flying around today. I’d like to clear a few things up. First, Joe and I did split but it wasn’t over the phone. Things didn’t work out but we’ll remain friends. Secondly, I am NOT dating anybody already. Nothing is more important to me than the relationship I have with my fans. Just thought you guys should know this.”

And Joe, now a first-time dad with wife Sophie Turner, told People, “I realize over the time we have shared together that I feel I care more about our friendship right now. It was my choice to break up but I love her as a friend. She’s been there for me when I needed her. I will continue to be her friend and be there for her.” 

That seemed to work until that November in 2010, when Demi abruptly left the tour after deciding in Peru that she just couldn’t continue and checked into rehab.

As she has since talked about in raw interviews, in song lyrics and in her 2017 documentary Demi Lovato: Simply Complicated, her struggles with an eating disorder and drug abuse prevented her from having truly healthy relationships for a long time because she was so down on herself. But her friendship with Joe—and Nick Jonas, whom she’s also toured with—has endured.

“It’s cool to be able to have, I think, friends in this music business but also I think it’s way different, we’re family at this point,” Joe, promoting DNCE at the time, told Access Hollywood when he and Demi sat down for a joint interview in 2016. “We’ve all gone through so much, good and bad, but we’ve watched each other through the sidelines or supported each other…” Demi added “And I’m so proud to have watched you evolve with DNCE.”

Asked what she called Joe if Nick was her “best friend and brother,” Joe cut in. “A lot of names,” he quipped.

They denied that Demi was “leaning on him” after (and maybe a little before) her breakup with Joe, but not doubt Demi was already friends with the That ’70s Show star—who’s 13 years older than she is—after they met in January 2010 while shooting a PSA about the importance of participating in the U.S. Census.

“To be honest, I only did it because I heard [the shoot] was at his house and I thought he was really cute,” Demi admitted in Simply Complicated. And she thought he was great all the way back then, “but I was only 17 and so, he was like, ‘Get away from me.'” 

They started dating at the end of 2011, though, and spent the majority of the next five years together, sparking as many engagement rumors as breakup rumors along the way.

“To the funniest, most inspiring, incredible man I know..,” Demi wrote to Wilmer on his 34th birthday in 2014. “Thank you for helping me get through my darkest moments.. You truly are a light to this world and to my life.”

Over the course of their relationship, Demi got sober (more than once) and has always credited Wilmer with being incredibly supportive and there for her along the way. They ended their romance amicably in 2016 (“It had nothing to do with falling out of love,” Demi said in her documentary) and did indeed remain dear friends. Wilmer was one of her first visitors in the hospital when she accidentally overdosed in July 2018, arriving and leaving on his own.

When he got engaged to Amanda Pacheco in January, a source told E! News that Demi was “happy for Wilmer if he’s happy. She always wants the best for him in life and is glad he has found love. They will always be friends and have a special place in each other’s hearts.

“But,” the insider added, “she also realized he wasn’t going to be her life partner and she’s known that for a while. She moved on from that and has been going in a different direction. She wishes him all the best though.”

Let’s not forget that the world tried to hook her up with the One Direction heartthrob during one of her breaks from dating Wilmer. 

But as Demi told Teen Vogue in the fall of 2012 about Niall, “He’s a really awesome, sweet guy. But he’s not my boyfriend…I’m in a place right now where I really need to focus on myself.”

She continued, “Obviously, I’m still going to like people—or love them—but I need to not be in a relationship for a while because I need to be OK with being alone, first. I’m really happy right now. I never thought it was possible to be happy because of how depressed I was my entire life. But I feel so incredible. It’s like living in a dream.”

She and Wilmer had rekindled their romance by the following Valentine’s Day.

In the summer of 2016, Demi took advantage of her single-for-the-first-time-in-ages status and made friends with then-New York Giants star Odell Beckham Jr. (now a member of the Cleveland Browns). The sharp-dressing, Met Gala-attending wide receiver thought the singer was “really dope” and reached out to her, a source told E! News at the time.

“Odell is aware that Demi broke up with her long-term boyfriend Wilmer not long ago but he really digs her,” the source said, noting he was the one who reached out to her first. “They are just hanging out now and it all is very fresh. Odell is aware that he may be a rebound, but he is OK with just chilling and getting to know her.”

Following her terrifying overdose in July 2018, Demi spent three months in treatment.

Toward the end of that year, she started keeping company with Henry Levy, founder of luxe streetwear label Enfants Riches Déprimé (under his professional name Henri Alexander). They spent New Year’s Eve in Aspen, Colo., but had split up by March 2019, it ultimately not being the right time for Demi to get serious as she worked to reestablish her long-term sobriety. (Despite some reports calling him as much, we were told that Henry was never an official “sober companion.”)

Instead, she entered treatment again, “for her mental health issues and not because she relapsed,” a source explained to E! News when we got word of the breakup. “Demi knows she will be battling her struggles for a very long time and wants to take precautionary measures when she feels the need to check in on her health. She never wants to get to a place where she was last year when she relapsed.

“Demi and Henry decided to split because none of her family members approved of her getting into a relationship so quickly and wanted her to focus on herself and her health. Demi felt distracted and overwhelmed, and wanted to take a breather and truly get healthy.”

In September 2019, Demi joined the alum of Hannah Brown‘s season of The Bachelorette for dinner in L.A. We don’t know if any roses were exchanged, but it was at least the start of a new friendship. 

This time, it was Demi who “always had a huge crush on Mike,” a source told E! News, “and once they met in person, there was an instant connection.”

The insider added, “Demi is not looking for anything serious right now but is staying open and is excited to see Mike again.”

Mike concurred, telling E! News at the 2019 iHeart Radio Music Festival, “I’m just getting to know Demi. I think she’s absolutely fantastic and I don’t want no pressure on her, no pressure on me, we’re just trying to get to know each other.”

A few weeks later, Mike was once again ready to mingle, throwing it out there during an appearance on Strahan, Sara & Keke that if by any chance host Keke Palmer was interested in a date sometime…

A couple of months after her brief trip to Bachelor Nation, Demi started seeing model Austin Wilson, someone she had met through her new circle of mostly sober friends.

“Demi loves that they share the same values and are on the same page about their health and well-being,” a source told us. “Demi thinks he is a good influence and a positive light to be around.”

But you know how tough dating during the holidays can be. By the end of 2019, they weren’t a couple any longer. 

“Their lifestyles were not meshing,” a source informed E! News, “She’s very focused on her sobriety and God and it wasn’t a good fit for that. She’s still working on herself and committed to that. She’s sticking with what she has been doing and working on her music. That’s her focus and nothing is going to change it. They decided it was best to go their separate ways. There are no hard feelings it just wasn’t going to work with him.”

May her relationship with the Young and the Restless actor remain as solid as the $1 million rock he gave her.

They went mildly public in March, exchanging a few comments on Instagram for all to see, but it turned out that they had already quaran-teamed up for social distancing, together at Demi’s house.

“Max is very into music and health, and he doesn’t like to party,” a source told E! News. “He is a good influence on Demi and they have a lot in common. They have a few mutual friends in common, but Demi has been introducing Max to her closest friends via FaceTime since being quarantined. It’s very new but they are definitely hanging out and seeing where it leads. They have spent a lot of time together but I wouldn’t say it’s an exclusive relationship yet.”

In May, Demi posted a video of them dancing to Ariana Grande and Justin Bieber‘s “Stuck With U,” captioned, “Happy to be a part of something so special right now. Like really REALLY happy if you can’t tell… #stuckwithu.”

Two months later, they were engaged.

Sure, it all happened fast, but what’s wrong with being confident in their long-term potential?