Demi Lovato was 18 when she dated Wilmer Valderrama, 29. She says the age gap was 'toxic'.

Demi Lovato is reflecting on her past relationships with older men.

Appearing on The Howard Stern Show this week, the singer said she believes they were motivated by "daddy issues" that she has since worked through.

"I think what I went through is that I had a phase of dating older men and dating older guys," Lovato recalled. "I went through a phase where I was attracted to older guys because of my daddy issues, obviously."

"I look back on the past and think, 'That’s gross. I was a teenager.' And so, to me, that’s gross," she said.

"I think that when you’re in those developmental years, you should absolutely not be with somebody that is older than you by that much," she added. "It’s just unhealthy and toxic."

Although the singer doesn't name any of her exes in the interview, it's hard not to remember her relationship with That '70s Show actor, Wilmer Valderrama.

Watch: The trailer for Demi Lovato's 2021 documentary Dancing With The Devil. Post continues below video.

Last year, Lovato seemingly referenced Valderrama in her highly anticipated song '29'.

"Finally 29 / Funny, just like you were you at the time," she sings.

"Thought it was a teenage dream / Just a fantasy / But was it yours or was it mine / 17, 29."

There's also: "Petal on the vine / Too young to drink wine / Just five years of bleeders, student and a teacher / Far from innocent / What the f***'s consent? / Numbers told you not to / But that didn't stop you."

In the second verse, Lovato points to a pattern of behaviour: 

"Had me in your grip, went beautifully with / All my daddy issues and this shit continues / I see you're quite the collector
Yeah, you're twelve years her elder."

Valderrama's wife Amanda Pacheco is also 12 years his junior. She is 30, while he is 42.

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Lovato and Valderrama met in January 2010, when they were 17 and 29, respectively. 

Lovato has said in the past that their relationship didn't begin until she turned 18 (her 18th birthday was eight months later, in August). They were on and off for six years until ending for good in 2016.

In 2015, Lovato spoke about the beginnings of their relationship.

"We shot a PSA together for the 2010 Census forms for Voto Latino," she told Complex. "We shot them at his house, so we actually met there. Of course, I was like, 'Oh my god. You're so attractive.' And he was like, 'You are not 18. Get away from me.'

"Then we became really good friends, and he was there for me through a number of situations and breakups and whatever. Then as I got older, and we grew closer, it was like, 'Hey, maybe we should try this thing out.' We did, and we've basically been together ever since."

They appeared to have remained on good terms after they broke up. Valderrama got engaged to his now-wife, Pacheco, in early 2020 and a source told E! News at the time that Lovato was happy for her ex, and that they'd "always be friends".

Following Lovato's (alleged) call-out of Valderrama, there was some revived chatter about his sequence of relationships throughout his 20s and 30s.

Image: Getty. 

Valderrama dated Mandy Moore from 2000 to 2002, beginning when she was 16. They had met at a photoshoot for a teen magazine when she was 15.

"He was like my first, real, true boyfriend," Moore said years later.

In 2006, Valderrama, who is four years older than Moore, appeared on Howard Stern's radio show and made inappropriate comments about a number of his exes during a game in which he ranked his sexual experiences with famous women. 

During this, he claimed to have taken Moore's virginity.

"I dated him when I was 16-17, no. I love him and I still love him and he's a very good friend, and that's why I was so shocked by it. Not only was it a fib, but it was so unlike him, it was so uncharacteristic," Moore told Stern in 2018, about 12 years later.

"[I asked] 'Where did this come from?' I remember in the moment he tried to explain it away; tried to say he insinuated it rather than outright said it. I was like 'No, you outright said it. Why would you ever talk about that with anybody? And lie about it?'"

After Moore, Valderrama dated Lindsay Lohan for less than a year in 2004.

Lohan was 18 and Valderrama was 24 when they publicly debuted their relationship, but they were first spotted together three months earlier when she was 17.

Image: Getty. 

At that year's Teen Choice Awards red carpet, Valderrama said they had kept it under wraps "because it is a lot more meaningful that way".

About five years later, he met 17-year-old Lovato for the first time.

Once is change, twice is coincidence, and third is a pattern.

And honestly, this is without getting too much into the parallels between Lohan and Lovato at the time of their relationships. Each were teen stars with mental health and addiction issues, who also had strained family relationships and released songs about their estranged fathers at similar stages of their careers (see: Lohan's 'Confessions Of A Broken Heart (Daughter to Father)' and Lovato's 'For The Love of A Daughter').

Lovato even name checks her "daddy issues" in the song, but that is a whole other can of worms.

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A post shared by Demi Lovato (@ddlovato)

"I've definitely been through a ton, that's no secret to the world. After going through even more stuff last year, I came out of treatment again and I realised, I really want to do this for myself and I want to make the best album possible, something that really represents who I am," Lovato told Jimmy Fallon in June 2022.

"The best way to do that and the easiest way to do something the most authentic is to do it clean and sober. I made this album clean and sober. I can't say that about my last album, but this one, I'm really, really proud about."

Chelsea McLaughlin is Mamamia's Senior Entertainment Writer and co-host of The Spill. For more pop culture takes, recommendations and sarcasm, you can follow her on Instagram. 

This article was originally published on August 5, 2022 and has been updated.

Feature image: Getty.