15 Celebs Who Don't Know How To Be Single

The world is a much different place than it was some 40 odd years ago. For example, one doesn’t HAVE to be in a relationship to lead a fulfilling life; we don’t have to have children or build some sort of dream Camelot-like family. We can be strong, independent individuals who revolve our lives around our career (which isn’t sneered at these days, by the way) or personal lifestyle. IT’S NOT FROWNED UPON ANYMORE, PEOPLE. However, these 15 celebrities apparently didn’t get that memo and don’t want to be defined as a loner or, heaven forbid, a spinster. While it’s not a bad thing to be a serial dater, these 15 don’t seem to ever take a second to catch their breath when running from relationship to relationship. Some even believe they’re really nothing unless they’re paired off like animals marching onto Noah’s Ark. Wake up – it’s 2017 for crap’s sake.

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15 Kim Kardashian

Ah yes, THIS Kardashian sister – the most recognizable one. Anyone who watches Keeping Up with the Kardashians understands that while Kim Kardashian claims to be the hopeless romantic type, she’s just terrified of ending up alone (yeah, right). In the days before Kanye West, it was her relationships that helped build her entire empire. She was married by 19 to a music producer named Damon Thomas, whom she divorced after a short time, jumped into a relationship with Ray J – yeah, THAT Ray J, the tape dude – not to mention all the guys who came afterwards which included Nick Lachey, Nick Cannon, The Game, etc, etc. Oh, and remember her six second marriage to NBA player Kris Humphries? That was a fun time. As we all know, she’s married to West now and has two children. Hopefully this one is a keeper.

14 Bella Thorne


Considering the fact that this girl isn’t even out of her teens yet, to be labeled as a serial dater already is quite impressive. She already has a pretty impressive resume to match: actress, singer, author, dancer, so how she finds time to include relationships in that fold is beyond me. Despite her busy schedule, Bella Thorne has been linked both officially (and unofficially) with a slew of gorgeous men/boys. She was in a long term relationship with Tristan Klier and is currently rumored to be with NBA star Jordan Clarkson, but there are supposed flings tossed in the mix including Jake T. Austin, Kenton Duty, Chandler Parsons, Garrett Backstrom, Cody Simpson, and Ross Lynch (so, basically all her co-stars she’s rumored to have been dating). She was even caught kissing ANOTHER dude (Ryan Nassif) after she confirmed her relationship with Brandon Lee. About a year ago, Thorne also came out as bi to her Twitter followers, so I expect this list to continue to grow in the coming years.

13 Rihanna

Rihanna has been a very busy woman for the past decade. Not only is she busy making hit albums, starring in films, designing clothes, and modeling, but like Thorne before her, she manages to relationship hop along the way. Currently, Rihanna is taking a breather from the dating world (Yay!), or so she says, and no one can blame her considering her torrid past relationships. As we all know, Rihanna was in a serious relationship with singer Chris Brown who physically assaulted her and even went back to him a few times following multiple assaults. In between the Brown love, Rihanna tried to move on with baseball player Matt Kemp and (most notably) Drake. She’s also been linked to Travis Scott, Ryan Phillippe, Rashard Lewis, Shia LaBeauf, Jay Z, and Leonardo DiCaprio. Considering that Rihanna’s usually linked to ALL of Hollywood, it’s refreshing to see her focus on her independence for the time being.

12 Leonardo DiCaprio

I’m not one to toss the word “man-whore” around lightly, but if I sense someone is on that path, I’m gonna call the dude out (I’m looking at you, Mr. Parsons). Titanic heartthrob Leonardo DiCaprio has been walking that path for years, and appears to be damn proud of it. Currently he’s in a so-called committed relationship with Danish model Nina Agdal, but his past is littered with a bunch of Nina-lookalikes. Excluding his relationship with former co-star Claire Danes, DiCaprio has a claim on all the blondes in the model world. He’s dated Gisele Bundchen, Paris Hilton, Erin Heatherton, Simone Holtznagel, Bar Refaeli, Ashley Roberts, Blake Lively, Alesia Riabenkova, Barbara Palvin, Toni Garrn, Kelly Rohrbach, and Georgia Fowler. He’s also been linked to Lindsay Lohan, Kate Moss, Alica Silverstone, Rihanna, Carmen Electra, and Sienna Miller. I'm always wildly surprised I never see Kate Winslet on his hit list, but they've openly expressed they could never be in a relationship with each other since they're such close friends (I'm pretty sure she's the only woman he doesn't see as an object, but rather an equal).

11 Taylor Swift

Talk about a serial dater. In all the time she’s been in the limelight, I’ve never known Taylor Swift to be single for even one solitary second. I used to think that was because she finds inspiration for her craft while being in a relationship, but now I think the girl just hates being alone. From Harry Styles to that one Kennedy to that other Taylor, the singer knows how to snag a boyfriend – she just doesn’t know how to keep one. I think that when she knows she’s nearing the final swan song days of her weekly beau, she hops on celebrity Tinder or Bumble or whatever.com and swiftly lines up another one for the following week. I’ve always wondered WHY she couldn’t hold on to a guy for very long, but I figure since she’s the common denominator in all her failed relationships, it has to be something she does... or sings.

10 Adam Levine

Usually, when a famous male actor/singer/model cannot seem to settle down, he’s seen as a womanizer or a cad and hailed for it. We get it, it’s how men are seen these days – they can’t possibly just be lonely because they’re men. While this is sometimes true, this doesn’t appear to be the case for singer Adam Levine. Before marrying Behati Prinsloo back in 2014, Levine appeared to be constantly drunk off model pheromones and on a quest to finally find “the one”. He had relationships with Anne Vyalitsyna, Arielle Vandenberg, Angela Bellotte, Becky Ginos, Maria Sharapova, Jessica Simpson, and Jane Herman. And those were just his official relationships! He was also linked to Lindsay Lohan and Cameron Diaz. After learning all of his past loves, it’s fun to listen to his music and attempt to match a song muse with a past girlfriend.

9 Lindsay Lohan

Hello Giggles

Actress Lindsay Lohan has had her share of trouble in the past, but something she never had a problem with was being able to land a date. In the past, she was engaged to everyone’s favorite “foreigner”, Wilmer Valderrama of That 70’s Show fame. But their relationship seemed to fizzle out when all her troubles started. Before him, she was with Aaron Carter and Damien Fahey. Post Valderrama seemed like a fun time too with Jamie Dornan (that 50 Shades of Grey dude), Bruce Willis (!!!), Robbie Williams, Calum Best, Samantha Ronson, Riley Giles, Heath Ledger (RIP), Jeremy Greene, Lady Victoria Hervey, Vikram Chatwal, Oscar Lusth, and Gavin Doyle. Things started to finally look up for Lohan when she became engaged to Egor Tarabasov back in 2016 and started to work on mending her past, but as we know, the duo are no longer together. It’s possible that she’ll just jump right back into her serial dating ways.

8 Chandler Parsons

USA Today

When Memphis Grizzlies’ forward Chandler Parsons burst onto the NBA scene, he was this tall, gangly boy with baby blue eyes and a killer smile. Now, he’s a player on the injured reserve list who is living it up with his jet setting, model dating ways. Back when he was playing for the Dallas Mavericks, Parsons was known to often show off then girlfriend Toni Garrn, a Victoria's Secret runway model. After he moved on to Memphis, he broke up with the model and started dating Kendall Jenner, Savannah Chrisley, and Bella Thorne. Before Garrn, he was in a relationship with Christina Perri, and Robyn Crowley. While he has progressed from that nerdy looking boy to a full fledged hunk, he still doesn’t really know how to be alone and appears to be constantly on the hunt for his next relationship. He’s even been known to “slide into the DMs” of attractive fans via Twitter or Instagram. Calm your roll there, pretty boy.

7 Madonna


Sure, this pop queen has been married twice in her life – both of which lasted longer than a year – but Madonna’s dated nearly everyone in Hollywood and the sports world. Back in the 1980’s when she was tearing up the pop charts, Madonna fell in love with and married actor Sean Penn. It only took four years for the odd pair to crumble and Madonna straight up dove right back into the dating pool head first. Before Penn, Madonna dated David Blaine, Dan Gilroy, Mark Kamins, Jean Michel Basquiat, and even had a lesbian relationship with Sandra Bernhard DURING her marriage to Penn. After Penn, she hopped back on the wagon with the man himself: John Kennedy Jr. She had a string of famous romances following John-John, which included Warren Beatty, Tony Ward, Vanilla Ice (ew, but why), Jim Albright, Jenny Shimizu, Dennis Rodman, and Tupac Shakur before marrying director Guy Ritchie in 2000. They too divorced and Madonna started dating Alex Rodriguez, Idris Elba, and Brahim Zaibat. These days, Madonna is single, but I don’t see that lasting more than a few hours.

6 Britney Spears

How I long for the days where the world was freaking out over Britney Spears’ magical melt-down and famous “oh holy crap, she went and shaved her head” debacle. Becoming a mega, super teen pop star at a young age is never easy, and the former Mickey Mouseketeer handled it the best way she knows how: by going crazy for a couple years and coming out completely clean on the other side. Back in her youth, Spears famously dated Justin Timberlake at the height of her pop-stardom (remember when they both claimed to be pure? Hahahaha, sure thing guys) before moving on with Fred Durst. She then had a random marriage to someone named Jason Alexander (no, not George Costanza) for six seconds before divorcing. She then turned around and married douche-nugget Kevin Federline, which lasted all of three years. She dated low key people after her second marriage fizzled out. Currently, she’s in a relationship with someone named Sam Asghar.

5 Colin Farrell


I used to think that it was a rite of passage that if you became an actress in Hollywood, you had to nail Irish actor Colin Farrell, who has a pretty known track record when it comes to the bang-train. He’s dated Angelina Jolie, Michelle Rodriguez, Britney Spears, Lake Bell, Carmen Electra, and had flings with Demi Moore, Rihanna, and Ashley Scott. However recently, he dropped a bombshell on the public when he revealed to Ellen DeGeneres on her daytime show that he was in a two year relationship with the late Elizabeth Taylor. This shocked people since Taylor was 76 at the time and Farrell was 32. He said that toward the end of her life, he became extremely close to the icon, though they never ended up consummating the relationship. It’s amusing because back in her heyday, it was Taylor who was the known serial dater. Farrell still wishes he would have been husband number eight.

4 John Mayer

Ah, this cooer who has wooed so very many women with his soulful voice and heart shattering lyrics. Yes, much like Taylor Swift, singer John Mayer would often draw inspiration for his songs from his relationships. Remember when we all knew that “Your Body Is a Wonderland” was inspired by then girlfriend Jennifer Love Hewitt? The tables then turned on him when he actually dated Swift for about a month before breaking it off with her, which caused her to write the song “Dear John”. The then 19-year old singer accused Mayer of playing games with her heart (something she appears to be guilty of in the long run) and for leaving her. Mayer has also famously had relationships with Jessica Simpson, Jennifer Aniston, and Katy Perry. At the time it was looking like there was going to be wedding bells in Perry and Mayer’s future, but like all people who can’t be monogamous, the two broke it off.

3 Bradley Cooper


I remember thinking that actor Bradley Cooper sort of looked like a Picasso painting when he first hit the scene back on the show Alias. Little did I know he would rip down the Hollywood wall by starring in The Hangover franchise and start dating Hollywood “It” girls by the dozen. His most notable relationships include Victoria Keon-Cohen, Isabella Brewster, Renee Zellweger, Zoe Saldana, and even the younger Suki Waterhouse, a relationship he took some heat for. His rumored hook-ups are even more impressive: Jennifer Lopez, Cameron Diaz, Denise Richards, Olivia Wilde, and Melanie Laurent. As of late, Cooper has been in a seriously relationship with Irina Shayk. While the relationship shows no signs of distress, we all know how serial daters work, and Cooper is certainly one to look out for.

2 The Olsen Twins


Even though these two are rarely seen without EACH OTHER, both Mary-Kate and Ashley Olsen are hardly ever single themselves and constantly need a man in their lives to balance out their twin relationship with each other. Mary-Kate has been in relationship with a number of men, including David Katzenberg, Heath Ledger, Lapo Elkann, Max Snow, and Nate Lowman. In 2015, she married 47-year old French businessman Olivier Sarkozy. Sister Ashley’s most high profile relationships include Matt Kaplan, Scott Sartiano, Greg Chait, Lance Armstrong, David Schulte, and was even engaged to actor Justin Bartha for a while. Currently, she’s dating George Condo (yeah, I have no idea who that is either). Despite their odd dating habits, at least these two know they will never be single due to their bizarre attachment to each other.

1 Kylie Jenner

In realty TV star Kylie Jenner’s 19 years on earth, she’s dated more people than someone twice her age. Also, she dated someone almost twice her age when she was 16, so…yeah. As we all have been made aware of, Jenner had a tawdry relationship with the 25-year old (at the time) Tyga when she was just 16 years old and the world was permanently shook. Of course, neither would officially “confirm” that they were a couple, but there were sightings of them making out all over the place along with suggestive Instagram posts from both. On her 18th birthday, when she finally became legal to get it on with, Tyga bought his girlfriend a Ferrari – a standard “YOU’RE NOW AN ADULT I CAN LEGALLY DO!” gift. Pre-Tyga, Jenner dated Ramsey IV (when she was just around 10-years old), Cody Simpson, Jaden Smith, and Justin Bieber. Post-Tyga, she’s been linked to PartyNextDoor and is now being seen with Travis Scott. Hopefully she finds time in between relationships to perform up-keep maintenance on her face with her plastic surgeon.

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