Adam Levine’s marriage has recently made headlines after Instagram model Sumner Stroh claimed she had a “physical” affair with the singer in 2021.

In September 2022, immediately after the rumors began to circulate, the Maroon 5 frontman denied that he had a yearlong dalliance with Stroh. However, he did admit to crossing a line.

Here’s a look back at his dating history over the years — from his relationship with high school sweetheart, Jane Herman, to his longtime marriage to Behati Prinsloo.

Jane Herman

Herman and Levine dated for four years before calling it quits.Patrick McMullan via Getty Image
Back in 1997, when he was just 18 years old, Levine began dating Jane Herman. They were together for almost 4 years before going their separate ways in 2001.

Maroon 5’s 2002 debut album, “Songs About Jane,” touched on Levine’s teenage love with hits including “This Love” and “She Will Be Loved” shining a light on their four-year, pre-fame relationship.

Jessica Simpson

Jessica Simpson reportedly hooked up with the singer back in the day.WireImage
Levine and Jessica Simpson were rumored to have hooked up in January 2006, with reports claiming they had spent a night together at the Chateau Marmont Hotel in Los Angeles.

The morning after, the “With You” singer was photographed being picked up by her best friend, CaCee Cobb, while wearing the “Harder to Breathe” crooner’s white T-shirt.

Levine was said to have ended their fling via text message.

Cameron Diaz

Cameron Diaz was spotted on a date with Levine.NBCU Photo Bank/NBCUniversal via
Levine and Cameron Diaz were seen having a lunch date at the Chateau Marmont — a clear favorite of his — in May 2009 following the actress’ breakup with model Paul Sculfor.

However, the duo did not seem to carry on with their relationship after their outing in LA.

Angela Bellotte

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Angela Bellotte dated the singer for less than a year.Getty Images
Levine and model-actress Angela Bellotte were spotted on a flight from LAX to New York City in September 2009 — just weeks after they were photographed holding hands.

However, the romance was also short-lived yet, ending less than a year later.

Anne Vyalitsyna

Levine and Anne V, as she is known, solidified their romance at the Victoria’s Secret Fashion Show in 2011.WireImage

Levine and Anne V, as she is known, solidified their romance at the Victoria’s Secret Fashion Show in 2011.Getty Images

Levine and Russian model Vyalitsyna reportedly met at a Sports Illustrated Swimsuit Issue party in 2010, and the pair ended up dating for about two years.

The Grammy winner performed at the Victoria’s Secret Fashion Show in November 2011, where he showed some love for his girlfriend by giving her a kiss when she modeled past him. She also appeared in the music video for Maroon 5’s 2010 hit “Misery.”

Vyalitsyna broke things off with Levine in April 2012 by releasing a statement to People, which reportedly left him “blindsided.”

Behati Prinsloo

Levine was spotted with Behati Prinsloo for the first time in 2012.Getty Images for Baby2Baby

Levine was spotted with Behati Prinsloo for the first time in 2012.Getty Images

Levine was seen getting comfortable with another Victoria’s Secret model — Behati Prinsloo — just one month after his split from Vyalitsyna.

The pair were spotted kissing in Hawaii in May 2012 while heading to a friend’s wedding, but it was not all smooth sailing from there.

The couple took a short break in May 2013, during which Levine was caught with model Nina Agdal, but they got back together soon after.

Levine and Prinsloo married in Mexico in July 2014 and welcomed two daughters, Dusty Rose and Gio Grace, in September 2016 and February 2018, respectively.

Although the couple is still married — and expecting their third child — Levine found himself in hot water in September 2022 when Stroh came out with allegations that he had an affair.