Finding love in Hollywood is like looking for a needle in a haystack, with only a handful of celebrities finding the "one." On the other hand, several stars have been labeled serial daters, and apparently love the dating game.
While a celebrity like John Mayer has it all, he's known as one of Hollywood's top serial daters and can't seem to find a love that will last. Some of the most famous women he's been linked to include, Jessica Simpson, Jennifer Aniston, Taylor Swift, and Katy Perry, and as of 2021, he's still very much single and still on the prowl. Some of the celebs on this list may have given up their serial dating ways to finally settle down, but it's worth noting that it took them having to date several other celebs to finally find their partner.
10 Jennifer Aniston
Jennifer Aniston has had her fair share of ups and downs when it comes to finding love. Before she met and married Brad Pitt, the Friends star dated numerous men in Hollywood, including, Charlie Schlatter, Daniel McDonald, whom she called her "first love," Counting Crows frontman Adam Duritz, Tate Donovan, and Paul Rudd.
After her marriage to Pitt was shattered in 2005 because of cheating allegations, Aniston moved on and continued to casually date men like her The Break-Up co-star Vince Vaughn, John Mayer, Gerard Butler, and even got married and divorced again to Justin Theroux. Whew, that's one long list of exes.
9 George Clooney
George Clooney was believed to have given up on marriage after he got divorced from Talia Balsam in 1993. After his brief marriage, the actor went on to have long-term relationships with several women, including Celine Balitran, Lisa Snowden, Krista Allen, and Stacy Keibler.
However, Clooney is also known to have dated other A-list actresses for a brief period of time like Lucy Liu, Renee Zellweger, and Charlize Theron. Fans thought that Clooney would be a bachelor for the rest of his life until he met Amal Alamuddin, who he married in 2014 and has two children with.
8 Katy Perry
Katy Perry may have just welcomed her first child with Orlando Bloom in August 2020, but before she settled down with the actor, she dated quite a few men in Hollywood. The songstress was first linked to troubled actor Johnny Lewis back in 2005 and then began dating Gym Class Heroes lead singer Travie McCoy a year later.
Perry's relationships began to become more serious when she married comedian Russell Brand, but the two called it quits 14 months in. She has had an on and off relationship with John Mayer from 2012-2014 and has dated DJ and producer Diplo. Today, the star is happily engaged to Bloom.
7 Bradley Cooper
According to Fame1o, Bradley Cooper has been linked to several beautiful women in Hollywood like Jennifer Aniston, Jennifer Lopez, Cameron Diaz, and Zoe Saldana. His more serious relationships were with Suki Waterhouse for two years and, later, with model Irina Shayk, who he dated for four years and welcomed their first child together in 2017, and later announcing their split in 2019.
It doesn't seem like the actor is dating anyone as of right now, so fans will have to just take a good guess as to who the next lucky lady of Hollywood will be.
6 Cameron Diaz
Cameron Diaz has been married to Good Charlotte musician Benji Madden since 2015, but before they were an item, the actress was dating numerous men in Hollywood. The list is actually pretty long, but her most notable exes include, Matt Dillion, Jared Leto, Edward Norton, Jude Law, Justin Timberlake, and Alex Rodriguez.
Diaz has definitely parted ways with the dating game, but it is interesting to see which men caught the blonde beauty's eye back then.
5 John Mayer
If this article ranked the top serial daters in Hollywood, John Mayer would easily take the number one spot. The musician has dated a lot of women over the years, but the ladies who stand out the most include, Jennifer Love-Hewitt, Jessica Simpson, Minka Kelly, Taylor Swift, Jennifer Aniston, and Katy Perry.
His ex, Taylor Swift even went as far as writing a song about him, titled, "Dear John," which Mayer called "cheap songwriting."
4 Leonardo DiCaprio
Leonardo DiCaprio also lands on this list thanks to the several models and actresses he has been famously linked to. The Revenant actor's dating profile includes Claire Danes, Amber Valletta, Gisele Bundchen, Bar Refaeli, Blake Lively, Nina Agdal, and recently, he's been spotted with model Camila Morrone.
Surprisingly, DiCaprio and Morrone have been getting "pretty serious" since they began dating in 2017, as reported by Elle. It seems the actor might finally be ready to settle down.
3 Justin Timberlake
Justin Timberlake has an extensive dating history before he tied the knot to actress Jessica Biel in October 2012. The former NSYNC pop star has dated a slew of women in Hollywood, including Britney Spears, Fergie, Cameron Diaz, Alyssa Milano, and Jenna Dewan.
There are also rumors that Timberlake dated Olivia Munn in 2010, and actress Scarlett Johansson, when she starred in his music video for the song, "What Goes Around/Comes Around."
2 Jennifer Lopez
Jennifer Lopez has been married three times, and she'll be saying her "I Do's" for the fourth time to Alex Rodriguez. The songstress has one of the most interesting dating timelines, but luckily, her relationship with Rodriguez looks like it'll stick.
Her list of past exes in Hollywood include P. Diddy, Ben Affleck, Cris Judd, Casper Smart, and Marc Anthony, with whom she has two children.
1 Taylor Swift
Listening to Taylor Swift's songs, it's clear that she's had a lot of exes. At only 31-years-old, the songstress has dated many celebrities that included Joe Jonas, John Mayer, Calvin Harris, Harry Styles, and Jake Gyllenhaal.
Currently, the "Willow" singer is dating Joe Alwyn, and we're crossing our fingers that this one lasts, or we'll just get another amazing break-up song by Swift.