Looking Back On ‘Modelizer’ Adam Levine’s Bad Boy Dating Reputation

Adam Levine was no stranger to the world of A-list romance in the years before he got with current wife Behati Prinsloo.

Now, as that whole situation goes up in the air amid Instagram influencer Sumner Stroh‘s shocking affair allegations against the Maroon 5 frontman, we figured it might be worth a look back to see Adam’s Cupid-related trajectory.

Related: Instagram Model Was Giving Clues To Adam Levine Situation For MONTHS!!

It all started way back when in the bygone era of the late 1990s. Seems forever ago, doesn’t it?! But from there to here, the rock star has been all over the map.

Here’s how things have gone down…

Jane Herman

Maroon 5 broke out in a REALLY big way in 2002 when their debut album Songs About Jane hit the airwaves. The album’s title wasn’t made up out of thin air, either. There really was a Jane! From 1997 to 2001, Levine dated his high school sweetheart, Jane Herman, and then wrote much of the band’s initial release about their time together.

Tracks like She Will Be Loved and Harder to Breathe are set to long-ago memories of their young love, and This Love was an ode to the day of the pair’s difficult breakup in 2001. Levine didn’t talk a ton publicly about his time with Herman, but in 2004, he did uncover a little bit about their relationship.

In an interview with Rolling Stone, he explained some about the muse behind his early work, saying:

“I saw this girl at a gas station, and I fell in love with her. I wrote a song about her and played it in the store where she worked. It was an awful song. But she found out about this relatively psychotic boy. She was my muse for years… And then it kind of faded away.”

Faded away??

As for Herman, she went on to write for Vogue. Not too shabby!! Today, she owns her own fashion label — appropriately called The Only Jane — and is married to filmmaker Marc Webb. They have two young children.

Jessica Simpson, Maria Sharapova, and More

Thanks to Songs About Jane, Maroon 5 was an overnight success. With it, Levine got a LOT of attention from high-profile women in the Hollywood sphere. In 2005, he was briefly linked to tennis star Maria Sharapova, and in 2006, he dated A-list singer Jessica Simpson.

Levine and the Newlyweds alum infamously (allegedly!) spent a night together at a Hollywood hotspot that year. The late-night rendezvous drew paparazzi attention after Simpson was spotted leaving the lair in Levine’s t-shirt. Oh, the memories!

Jessica was just coming off the end of her marriage to Nick Lachey (pictured together here in 2004) when she got together with Levine. / (c) WENN/Cortes

Those romances were pretty short-lived, though. Levine was just entering his rock star phase, after all, and his bad boy reputation was only set to surge from there.

As if to cement that new bad boy vibe in stone, later in 2006, Levine allegedly broke things off with Simpson in a text message. Ouch! (FWIW, Levine has since denied that report.)

Rebecca Ginos

After some time as a single man, Levine’s love life piqued our interest again in 2007. That year, he was linked to El Lay-based cocktail waitress Rebecca Ginos.

After dating for a bit, Levine went on Howard Stern‘s radio show and revealed to the shock jock how he met Ginos at her 21st birthday party, and the two “had sex the first night we met.” Hmmm…

The Payphone singer spoke to Rolling Stone about this romance later in 2007, as well. He told the mag about how it grew into “something amazing” after its apparently-passionate beginning:

“We were casual at first and it turned into something amazing. She just wants to en­joy my company and love me. And I love her. It’s really simple and beautiful. When you’re younger, relationships thrive on dra­ma. And if there’s no drama, you’re bored and it ends. I’m not into that anymore. I know more about myself, which pre­pares you to figure girls out.”

Possibly a very telling old quote in light of some of Adam’s modern-day issues. Just saying!!!

Cameron Diaz

Simpson and Sharapova weren’t the only big stars to pop up early in Levine’s dating history. After splitting from Ginos, Adam was quickly linked to actress Cameron Diaz.

The two were first spotted on a lunch date together in 2009. Paparazzi photos led to gossip blog supposition, and the whole thing ballooned from there!

Cameron was briefly connected to Adam way back in the day! / (c) C.Smith/ WENN

In fact, the pair went back to the very same Hollywood hotspot where Levine and Simpson had previously made their mark. Repeat alert!

And Adam had a trick up his sleeve the second time, too: he and the Charlie’s Angels star wore coordinated outfits in matching white tops and blue jeans for the outing. Fun!!

The relationship didn’t last, but, hey, Cameron is living her best life at this point. So she’s moved on, at least!

The Model Era…

After parting from his brief fling with Diaz, Levine opted to take the model route for a while. German beauty Janine Habeck and actress Arielle Vandenberg made the cut for a while, then model Angela Bellotte dated the singer more seriously for a time to ring out the decade.

Levine actually shut down a lot of rumors about his love life around that time, too. In 2012, he spoke to Details about his reputation for lusting after lovely ladies, saying:

“There’s two kinds of men. There are men who are f**king misogynist pigs, and then there are men who just really love women, who think they’re the most amazing people in the world. And that’s me. Maybe the reason I was promiscuous, and wanted to sleep with a lot of them, is that I love them so much.”

Oof. Looking back now, that’s definitely a super-cringe quote. Yeesh!! Hindsight is 20/20, we suppose…

More models came around in the early 2010s — most notably a lengthy and more serious romance with Russian-American beauty Anne Vyalitsyna. The pair were pretty committed for a while, and she even appeared in Maroon 5’s 2011 video Never Gonna Leave This Bed. Sadly, they split up in April 2012.

Vyalitsyna apparently had no hard feelings towards Adam afterwards, even though gossip mags at the time alleged she was “blindsided” by the breakup. In a recent appearance on Fashion Police, she reflected on having lost out on love with the future star of The Voice:

“I’m such a believer in love. I will love [Adam] forever. He is such a wonderful guy. But we didn’t work out. We still care about each other. He fell in love with someone else. I’m so happy for him.”

Along Comes The One… Sort Of!

By June 2012, just a few months after splitting from Vyalitsyna, Adam and Behati were spotted on a trip to Kauai, Hawaii. But it wasn’t smooth sailing from there!

In fact, the pair — who were reportedly introduced by a mutual friend — first split up in January 2013. After that, Adam was linked to Gossip Girl star Amanda Setton. Months later, things with Setton were over, and Adam had reconciled with the Namibian-born catwalker.

But not long after that, later in 2013, the duo split AGAIN! Adam briefly dated another Victoria’s Secret model in the interim: Danish beauty Nina Agdal. They were spotted vacationing together in Cabo San Lucas that summer. Things didn’t last long there, either, and soon enough Adam was right back with Prinsloo once more.

The relationship moved pretty quickly from there: Adam and Behati announced their engagement later in 2013, and they got married in July 2014 — with actor Jonah Hill the officiant. How fun must that have been?!

Two years later, in September 2016, Adam and Behati welcomed their first child, daughter Dusty Rose, and two years after that they followed with a second daughter, Gio Grace.

Whew.

That was a lot! And now, well, here we are again. More alleged dating drama — only this time the stakes are obviously much higher, what with a wife and two children at home and a third on the way.

So, how do you think all of this is affecting his marriage? Well, on Tuesday, the two were spotted smiling for the cameras, so for the meantime at least, it seems he’s in the clear… for now…

Thoughts, Perezcious readers?? Share ’em down in the comments (below)…

[Image via MEGA/WENN/Avalon]

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