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Here's Every Guy Britney Spears Has Dated

A true cast of characters, including Criss Angel.

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1. Reg Jones


When they dated: The mid-'90s when she was still in high school.

Who is he: Someone from her hometown.

Why he's significant: He's one of Britney's first boyfriends and is one of the most iconic people from her hometown, Kentwood, Louisiana. Reg Jones is a legend. Also his name is Reg, which is weird and country. Very Britney. Very cool.

3. Wade Robson

Lawrence Lucier / Getty Images

When they dated: Not sure if they ever *officially* dated, but it's rumored that she cheated on Justin with him.

Who is he: Her choreographer.

Why he's significant: Those frosted tips. He also probs is the reason Justin and Britney broke up. Kind of problematic, but then again, Justin is a douche.

4. Fred Durst

Us Weekly

When they dated: 2002.

Who is he: A sad person.

Why he's significant: Apparently they were working on new music for Britney's album and it turned into something more. Fred was super heartbroken when Britney wouldn't return his calls or acknowledge the relationship. Sad.


6. Columbus Short


When they dated: The summer of 2003.

Who is he: He was a backup dancer for Britney and choreographed one of her tours. More recently, he was on Scandal.

Why he's significant: He's significant because he was an early warning sign that Britney had a fetish for backup dancers. See in the future: Kevin Federline.

8. Jason Alexander

Robyn Beck / AFP / Getty Images

When they dated: They got married in Vegas for 55 hours.

Who is he: Some rando from her hometown that was like a farmer or something. IDK.

Why he's significant: This was really just fucking crazy and random. He tried to milk her for money and fame but that shit didn't work. See also: sad loser.


9. Kevin Federline

Matthew Simmons / Getty Images

When they dated: They got married in like 2004 and divorced in 2007.

Who is he: A backup dancer who got so. incredibly. lucky.

Why he's significant: He provided the literal seed for Britney's two biggest joys, her children. That's it.

11. Criss Angel


When they dated: 2007, apparently.

Who is he: A magician with really aggressive style.

Why he's significant: Because isn't this random?!?! Apparently he was supposed to help her with special effects for her 2007 VMAs performance but that didn't work out.

12. Howie Day

David Livingston / Getty Images

When they dated: Supposedly in 2007.

Who is he: Some random singer who sang that song "Collide."

Why he's significant: He's irrelevant but it's just funny that Britney would even date him. No offense.


14. Matt Encinias

Us Weekly

When they dated: Pretty sure they never really *dated*, but they were in a hot tub topless/naked (?) one night in 2007 and ended up on the cover of Us Weekly. Iconic.

Who is he: Some random ass college kid.

Why he's significant: Britney wanted that college D, so she got that college D.

15. Adnan Ghalib


When they dated: 2007–2008.

Who is he: A paparazzo who ended up dating Britney during the dark days of 2007.

Why he's significant: He was there when Britney was going through some hard shit and it's hard for me to believe he was good for her. He also had that chin-strap facial hair, which I can never, ever forget.

16. Jason Trawick

Michael Kovac / Getty Images

When they dated: 2009–2013.

Who is he: He was Britney's manager, which is actually pretty problematic. Like, you shouldn't shit where eat.

Why he's significant: She almost married him! She also made him lose mad weight and get fucking ripped.


17. David Lucado


When they dated: 2014.

Who is he: Literally no idea. He was a truly random human being that just kind of appeared one day like a bad rash.

Why he's significant: He's a fucking sleaze. He cheated on Brit! He also wears plaid fedoras. Sad!

18. Charlie Ebersol

Jason Merritt / Getty Images

When they dated: For eight months in 2014–2015.

Who is he: A film producer with a really rich dad.

Why he's significant: He was cute, but Britney deleted all the pictures of him from her Insta when they broke up. Savage!

19. Harry Morton


When they dated: They only went on one date at the end of 2015 lol.

Who is he: He's best known as Lindsay Lohan's ex. He also is the CEO of the restaurant Pink Taco.

Why he's significant: He is the CEO of Pink Taco, which means he probably gets mad free Mexican food. That's a plus!

20. Sam Asghari

When they dated: It's not really official but she Instagrammed a picture with him this week which basically means, in 2017 terms, that they are official/boning.

Who is he: The hot guy in her "Slumber Party" video.

Why he's significant: He is, BY FAAAAAAAAAAAAAAR, the hottest guy Britney's ever dated.