Who Has Britney Spears Dated? A Look Back at the Pop Star’s Love Life

Britney Spears seems happier and healthier than ever with her personal trainer boyfriend, Sam Asghari. However, it’s taken the 36-year-old pop star plenty of trial-and-error to find what she was really looking for in a relationship.

From the mid-90s to now, here’s every man Spears has ever dated.

Reg Jones

Spears dated Reg Jones, a guy from her hometown, back in the mid-90s. She was still in high school at the time.

Justin Timberlake

Britney Spears and Justin Timberlake

Britney Spears and Justin Timberlake | UCY NICHOLSON/AFP/Getty Images

Who can forget the days of Spears dating Justin Timberlake? They were an iconic celebrity couple from 1998 to 2002, and wore an even more iconic matching denim outfit on the red carpet.

Wade Robson

It’s rumored that Spears’ romance with her choreographer, Wade Robson, was the reason she and Timberlake broke up. However, former *NSYNC member Lance Bass attests it never happened.

Fred Durst

In 2002, Spears had a brief fling with musician Fred Durst. According to BuzzFeed, “Apparently they were working on new music for Britney’s album and it turned into something more.”

Colin Farrell

Spears was romantically linked to Colin Farrell in 2003 after attending a movie premiere with him. On the red carpet for The Recruit, Spears and Farrell didn’t comment on their relationship, but they did share a steamy makeout session.

Columbus Short

In the summer of 2003, things got romantic between Spears and Columbus Short. He was one of her backup dancers and tour choreographers, but their relationship ended as a fling.

Jared Leto

Rumor has it that Spears briefly dated Jared Leto in 2003. This was quite the controversy at the time, considering Leto’s ex, Cameron Diaz, was dating none other than Spears’ ex, Timberlake. Spears claims, however, that she and Leto were just “really good friends.”

Jason Alexander

Spears’ first marriage was so quick, you’d have missed it if you blinked. After a night of partying in Las Vegas with her childhood friend, Jason Alexander, they made a spur-of-the-moment decision to tie the knot. The whole thing basically never happened, however, considering they annulled their marriage after just 55 hours.

Kevin Federline

Britney Spears and Kevin Federline

Britney Spears and Kevin Federline | Vince Bucci/Getty Images

2004 was a year filled with weddings for Spears. She got married again, this time to her backup dancer, Kevin Federline. They had two sons together, Jayden and Sean, but ended up getting divorced in 2007.

J.R. Rotem

Spears bounced right back after her marriage to Federline. She began dating music producer J. R. Rotem in 2007, but according to Us Weekly, many speculated their romance began while she was still married.

Howie Day

After Spears’ infamous breakdown, she entered rehab in February 2007. While at Promises rehab center in Malibu, California, she met musician Howie Day. The two reportedly started dating, but after Spears’ mother learned Day had previously been arrested, they called it quits.

Criss Angel

When illusionist Criss Angel helped Spears with an MTV Video Music Awards performance, rumors circulated that the two were romantically involved. Angel, however, has denied any kind of relationship.

Adnan Ghalib

Most celebrities try to escape the paparazzi, but Spears somehow ended up doing the exact opposite. She and paparazzo Adnan Ghalib dated from 2007 through 2008, while Spears was still working through her breakdown.

Jason Trawick

Spears finally found herself in a stable relationship in 2009 — but it was with her now-former manager, Jason Trawick. They ended up getting engaged in December 2011, but called it off in January 2013.

David Lucado

After Spears and Trawick broke off their engagement, Spears began dating David Lucado. They seemed happy until Spears caught him cheating on her in a TMZ video. According to The Daily Mail, he was “making out with a woman and dancing with her,” leading Spears to end their relationship.

Charlie Ebersol

Spears dated film producer Charlie Ebersol for eight months between 2014 and 2015. According to Buzzfeed, Spears deleted all evidence of their relationship from her Instagram account when they broke up, so they probably didn’t split on good terms.

Sam Asghari

Ever swim so much that you start to feel like a fish? @samasghari

A post shared by Britney Spears (@britneyspears) on

Spears met Sam Asghari on the set for her “Slumber Party” music video, and the rest is history. She and Asghari seem crazy about each other, making regular appearances on each other’s Instagram pages. It may have been a long path for Spears, but it seems like she may have finally found the one.