Adam Levine's Road to Engagement: A Timeline of His Many Girlfriends

As the Maroon 5 frontman prepares to walk down the aisle, let's take a look back at his dating history—including the stars who just turned out to be rumored gal-pals

By Bruna Nessif Jul 17, 2013 4:10 AMTags
Adam Levine, Fragrance LaunchChristopher Polk/Getty Images for Adam Levine Fragrances

Congratulations, Adam Levine. Sorry, Adam Levine's many admirers.

You may have heard—either by the shriek from your neighbor or the sobbing phone call from your bestie—that the hunky musician has popped the question to girlfriend Behati Prinsloo, shattering the dream of many who hoped of one day becoming his next love interest.

(No, but really, congratulations.)

The singer's rep confirmed to E! News today that the Maroon 5 frontman is engaged to Prinsloo after proposing last weekend in Los Angeles.

And it's been a long road to the altar for Levine, who has even admitted himself to being "promiscuous" in his day, so why not take a trip down memory lane and rehash this stud's dating history?

There just might be a few names you never even knew had been linked to the ladies' man...

J. Vespa/WireImage

Jane Herman: Levine dated his high school sweetheart, and former Vogue editor, for four years (1997-2001).

In fact, Maroon 5's album Songs About Jane, which includes the hits "Harder to Breathe," "This Love," and "She Will Be Loved," was inspired by that romance.

There's no word on what caused the breakup, but we're guessing life just got in the way.

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Jessica Simpson: Wait, what?! Yes, they were rumored to have hooked up.

In 2006, reports claimed the duo spent the night at L.A.'s Chateau Marmont together and that Jess was seen wearing his T-shirt when her BFF CaCee Cobb picked her up the next morning—before Levine allegedly broke up with Simpson via text message.

Noel Vasquez/Getty Images

Rebecca Ginos: Levine reportedly told Howard Stern in 2007 about hitting it off with the cocktail waitress from Los Angeles hot spot Teddy's after meeting on her 25th birthday.

And they didn't waste any time.

"We had sex the first night we met," he said, before also sharing that he told his new gal-pal, "I think you're the hottest girl in the entire f---ing universe."


cocktail waitress at L.A. nightclub Teddy's.
cocktail waitress at L.A. nightclub Teddy's.

Cameron Diaz: Another bombshell!

In 2009, the actress was spotted having a lunch date with Adam following her split from model Paul Sculfor.

The pair dined together at the Chateau Marmont, and even started off on the right foot by coordinating outfits (both opted for blue jeans and a white top), but that's as far as this love story went.

However, the pair reunited early this year for a spoof on Saturday Night Live, so obviously they can stand to be around each other.

Andrew H. Walker/Getty Images

Angela Bellotte: Steering away from the blond trend, The Voice coach began dating this brunette beauty (and model) in 2009.

The couple were spotted catching a flight to NYC from LAX in September of that year, shortly after being photographed holding hands in the Big Apple.

They split less than a year later.

Noel Vasquez/Getty Images

Anne Vyalitsyna: One of his more memorable relationships (which produced an image we will never get out of brains), Levine and the Victoria's Secret model dated for two years (2010-2012) after meeting at a Sports Illustrated Swimsuit Issue party.

"Adam and I have decided to separate in an amicable and supportive manner," Vyalitsyna said in a statement after their split. "We still love and respect each other as friends. I wish him all the best."

Levine was reportedly "blindsided" by the breakup.

Leandro Justen/ USA

Behati Prinsloo: Shortly after he and Anne V. broke up, the celeb was spotted gettin' grabby with this Victoria's Secret model.

The duo were first spotted together in June 2012, stealing a smooch while vacationing in Hawaii. They were headed to Kauai for a friend's wedding and were seen holding hands and chatting up pals together during pre-ceremony festivities.

Levine and Prinsloo broke up for a bit in May of this year, but apparently decided to reconcile.

And now, Behati gets to keep Adam forever.

Brett Kaffee/Thibault Monnier,

Nina Adgal: During his short breakup from Prinsloo, Adam found comfort in—wait for it—another model.

Levine was seen vacationing in Cabo San Lucas, Mexico, with this blond bombshell. The duo were photographed playing volleyball in their swimsuits when not just relaxing on the beach.

Courtesy of NBCUniversal

Rumored Girlfriends: There are a number of other female stars that have been linked to Levine, but the A-lister cleared the air during an interview with Howard Stern, telling listeners that he did not date Natalie Portman, Kirsten Dunst or Paris Hilton.

He also mentioned that there was no romance with Maria Sharapova, though the pair did make headlines following their "breakup," when Adam threatened to sue a publication that claimed to know the reason why things didn't work out between the singer and the champion tennis player.