Actor and musician Kelly Blatz is Blake Lively's least famous beau. They dated for three years, starting in 2004. (Photo: Getty Images)
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Blake Lively dated her "Gossip Girl" co-star Penn Badgley from 2007 to 2010. (Photo by Aby Baker/Getty Images)
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Blake Lively and Ryan Gosling were an item in 2010. (Photos: Getty Images)
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Blake Lively and Leonardo DiCaprio were an item for five months in 2011. (Photo by Ethan Miller/WireImage)
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Blake Lively and Ryan Reynolds got married in 2012. They're expecting their first baby. (Photo by Jeff Kravitz/FilmMagic)
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Taylor Swift and Joe Jonas at the 2008 MTV Video Music Awards in L.A. The singers were an item in 2008. (Photo by Jeff Kravitz/FilmMagic)
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Taylor Swift and "Twilight" heartthrob Taylor Lautner dated in 2009. Swift's "From December" lyrics are thought to be about him: "I miss your tan skin/ Your sweet smile/ So good to me/ So right." (Photo by Jean Baptiste Lacroix/WireImage)
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Taylor Swift's song "Mine" is allegedly about her brief relationship with "Glee" star Cory Monteith (RIP!). Here the pair attend the Grammy Awards in 2010. (Photo by Rick Diamond/WireImage)
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Swift's song "Dear John" is about John Mayer, whom she also dated in 2010. The lyrics don't paint a flattering picture: "And I lived in your chess game/But you changed the rules everyday."
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Taylor allegedly wrote a song ("All Too Well") about Jake Gyllenhaal, too. She dated Jake the same year she dated John Mayer and Cory Monteith.
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Cory Monteith wasn't the only "Glee" actor Taylor spent time with. She also went out with Chord Overstreet, but it seems the two kept it super casual. Here the two are shooting a recreation of "Thelma & Louise." (Photo: Getty Images for CMT)
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Conor Kennedy is the first of THREE Kennedy's on our list. The two dated in the summer of 2012. (Photos: Getty Images)
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Taylor dated Harry Styles of One Direction fame in 2012-13. (Photo: Getty Images)
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Miley and Nick Jonas dated for more than a year back in 2006-07. (Photo by Jeff Kravitz/FilmMagic)
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There was a rumor going around Miley Cyrus and Justin Bieber hooked up, and that Selena Gomez wasn't happy about it. But no one knows if this is anything more than tabloid fodder. (Photo by Ethan Miller/Getty Images)
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Remember when Miley dated underwear model Justin Gaston?
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Miley once said that "Hunger Games" hunk Liam Hemsworth was her "first serious boyfriend." (Photo: Getty Images)
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There were rumors that Miley Cyrus dated producer Mike WiLL Made It. The two are photographed here at Miley's record release signing party in 2013. (Photo by Bruce Glikas/FilmMagic)
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Model and "Twilight" actor Kellan Lutz reportedly had a brief fling in 2013. The two are pictured here in Las Vegas. (Photo by Kevin Mazur/WireImage)
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Also in 2013, rumors surfaced that Miley Cyrus and Oscar-winning actor Jared Leto were "hooking up" in 2013. (Photo by Kevin Mazur/Getty Images for Clear Channel)
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Miley's current squeeze is Patrick Schwarzenegger, son of Arnold. His mom is Maria Shriver, which also makes him a member of the Kennedy clan. (Photo: Getty Images)
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Jennifer Aniston and Brad Pitt in 2001. (Photo: Getty Images)
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Jennifer Aniston dated Vince Vaughn after her breakup with Brad. The two attended the 2006 French Open. (Photo by Michel Dufour/WireImage)
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Jen was linked to British model Paul Sculfor in 2007. (Photos: Getty Images)
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Jennifer dated singer and ladies man John Mayer in 2008-00. The couple attended the Vanity Fair Oscar Party 2009. (Photo by Gregg DeGuire/ FilmMagic)
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After John Mayer, Jen dated "Sexiest Man Alive" Gerard Butler. The two attend "The Bounty Hunter" premiere in Madrid in 2010. (Photo: WireImage)
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Jennifer Aniston is tying the knot with actor Justin Theroux. (Photo by James Devaney/ WireImage)
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Katy Perry dated actor Johnny Lewis in 2005-06. Johnny died in 2012. (Photo: WireImage)
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Katy Perry and Travis McCoy were a couple in 2008-09. (Photo: WireImage)
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Katy Perry married comedian Russell Brand in 2010, and got divorced 14 months later. (Photo by Rob Kim/FilmMagic)
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Katy Perry began dating John Mayer shortly after divorcing Russell Brand in 2012. The two broke up in January, 2014. (Photo: WireImage)
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There was speculation that longtime friends Katy Perry and Robert Pattinson may be taking their relationship to the next level after the two were spotted kissing earlier this year. This photo is from the Teen Choice Awards in 2010. (Photo: WireImage)
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There were rumors that Katy and actor/musician Jared Leto may have gone on a date at Coachella this year. (Photo by Jeff Kravitz/ FilmMagic)
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Katy Perry is rumored to be dating producer/DJ Diplo. (Photos: Getty Images)
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Kim Kardashian and Michael Jackson's nephew, TJ Jackson, were an item in the '90s. (Photos: Getty Images)
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Kim Kardashian with sex tape partner Ray J.
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Kim Kardashian and Nick Lachey were an item in 2006. (Photo: WireImage)
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Before getting hitched to Mariah Carey, Nick Cannon dated Kim. This pic is from 2007. (Photo by John Shearer/WireImage)
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Kim dated running back Reggie Bush from 2007-10. The attended Fashion Week in NYC in 2010. (Photo: WireImage)
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Following Kim's break up with Reggie Bush, she dated another sports superstar - soccer player Cristiano Ronaldo.
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Reggie Bush wasn't the only football player Kim dated. She dated Miles Austin the same year she and Reggie called it quits. (Photo by Charley Gallay/Getty Images)
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And let's not forget NBA star Kris Humphries in 2011.
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Kim and Kanye West were married in 2014.
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Madonna dated artist Jean Michel Basquiat in 1982. (Left photo by Ron Galella; right by Frank Micelotta/Hulton Archive)
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Madonna hasn't dated men exclusively. There was also comedian Sandra Bernhard. The two are pictured here at the Rainforest Benefit in 1988. (Photo by Vinnie Zuffante)
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Madonna and Sean Penn were married from 1985-89, and she has stated that he was her "true love."
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In between her separation and divorce from Sean Penn, Madonna dated John F. Kennedy Jr. Photos by Brenda Chase (at left) and Ron Galella.
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Madonna dated the much older Warren Beaty from 1989-90. (Photo by Ron Galella/WireImage)
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Remember how Vanilla Ice was in her 1992 book, "Sex"? In the pic at left Vanilla Ice attends Madonna's screening for "Truth or Dare." (Vanilla Ice pic by Ron Galella)
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Madonna and former Chicago Bulls player Dennis Rodman were an item for two months in 1994.
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Madonna became involved with fitness trainer/actor Carlos Leon in 1995. The two had a daughter together, Lourdes. The two attended the 1997 Golden Globes. (Photo: FilmMagic)
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Madonna was married to filmmaker Guy Ritchie from 2000-08. (Photo by Francois Guillot/AFP/GettyImages)
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Madonna and A-Rod attended the 2009 Vanity Fair Oscar Party. (Photo by Kevin Mazur WireImage)
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Madonna and model Jesus Luz attend Marc Jacobs Spring 2010 show in New York City. (Photo by Gustavo Caballero/Getty Images)
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Madonna dated dancer Brahim Zaibat for three years. (Photo by Raymond Hall FilmMagic)
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Earlier this year she also dated another dancer, Timor Steffens.
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Vivica A. Fox dated Dennis Rodman in 1997. (Photo by Ron Galella/WireImage)
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50 Cent and Vivica A. Fox at the 2003 MTV Video Music Awards. (Photo by Jeff Kravitz/FilmMagic)
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Actress Vivica A. Fox and singer Ne-Yo attend an event in 2009. (Photo by Bryan Bedder/Getty Images)
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It may sound like Vivica A. Fox and Jamie Foxx are related, but it's rumored the two "Booty Call" stars dated.
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Vivica A. Fox was rumored to have dated Quentin Tarantino. In this photo, the two are at the 2004 MTV Movie Awards. (Photo by Gregg DeGuire/WireImage)
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Vivica A. Fox is rumored to have dated rapper Flo Rida in 2009.
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Vivica A. Fox and actor Omar White in 2011. (Photo by Jemal Countess/Getty Images)