10 Celebs Who Tried To Date Jen Aniston (And 10 Who Actually Succeeded)

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Jennifer Aniston will probably be America's sweetheart forever. At 49 years old, the actress is knocking every 22 year-old out the water, and we just can't get enough of her. Jen shot to fame as Friends' spoiled fashionista, Rachel Green, and the $1 million per episode paycheck proved to be pretty sweet in later seasons. Being mega-rich won't necessarily make you happy, though. If anyone has "heartbreak" written all over them in Hollywood, it's Jen. Her messy divorce from Brad Pitt following the arrival of a certain Angelina Jolie is still the most talked-about split in history, and no one saw it coming.

The twice-divorced (and now very single) Jen has had every man on the planet running after her–not surprising given that she's beautiful, funny, talented, and of course, absolutely loaded. Something about her girl-next-door charm has kept her totally real despite her net worth of $200 million, but Jen only seems to have bad luck when it comes to love. Jen has quite the dating portfolio, but whether they were rumored relationships, longterm connections, or marriages, they all failed. This hard-working, strong, and gorgeous woman has been jerked around more times than we can count, although for every guy she dated, 100 were waiting in line. Here are 10 guys who were lucky enough to date Jen (and 10 who tried but failed).

MATTHEW PERRY GAVE IT A SHOT

Ten seasons of Friends gave us plenty from characters, Rachel Green and Chandler Bing. While Rachel was adored for her fresh-faced beauty and snappy sarcasm, Chandler (played by Matthew Perry) was literally the funniest man on TV. Could we be more surprised to hear that he tried to date her in real life?

Chandler Bing never had much luck with women (until he got together with Monica Geller in season five). The actor did however attempt to date his co-star, Jen according to The Daily Mail. Neither of the two have ever confirmed it, although Matthew was not invited to Jen's second wedding to Justin Theroux. Is there something you guys aren't telling us?

BRAD PITT GOT FIVE YEARS OF MARRIAGE

And he threw it all away? What? Was having a girl with a heart of gold and the face of an angel just too much to handle? Brad Pitt and Jen were the biggest "it" couple of the 2000s, and with good reason.

Hollywood's hunkiest actor was finally with the decade's golden girl, and fans just couldn't get enough of them. Brad and Jen tied the knot in a lavish wedding, but there was trouble in paradise.

That "trouble" came by the name of Angelina Jolie (who already had a reputation for eyeing up unavailable men). Brad and Ange met on-set for movie, Mr & Mrs Smith, and it wasn't long before they were a couple. Angie has admitted that the two "fell in love" during filming, and it ended sadly for Jen in 2005, when Brad cut ties with her.

JON STEWART TOOK JEN TO AN ITALIAN RESTAURANT

Can you blame the guy for trying? Jon Stewart has spent most of his career behind the desk on The Daily Show. In 2010, his guest was none other than Jennifer Aniston, and it all turned pretty funny as they joked about the "awkward first date" they'd had over a decade earlier.

According to People, funny man Jon reminded Jen that they had shared a romantic Italian meal in a New York City restaurant.

"I asked you out," Jon said, continuing: "And I remember thinking, she's so excited to be on a date with me." Jen was quick to fire back, saying: "If I remember correctly, wasn't it sort of like, hey, a group of us are going out, do you want to join?" Ouch.

JUSTIN THEROUX GOT TO BE HUSBAND NUMBER TWO

That's right. If you want a chance with Jen, you need to wait in line. Following her failed marriage to Brad Pitt, it was onwards and upwards for Jen (kind of).

There were some boyfriends here and there, but Jen really felt she'd met "the one" with screenwriter and actor, Justin Theroux. She's even said that he makes the "best spaghetti carbonara ever."

After one year of dating, Justin popped the question, and the answer was a lucky "yes." Jen and Justin tied the knot in a 2015 Bel Air wedding. It wasn't long though before rumors were rife that their marriage was on the rocks. In February 2018, they announced their divorce, leaving Jen once again single.

OWEN WILSON WAS INTO JEN BECAUSE SHE'S FUNNY

And guess what? She is. Just watch any talk show interview with her–Jen is hilarious. Owen Wilson may be known for his relationship with Kate Hudson, but rumor has it the actor had his eye on Jen back in the day.

The two made a great on-screen couple in the movie Marley & Me, where The Daily Mail reported that they got along great, because he "made her laugh."

We won't hold this one against Owen. If it wasn't her awesome humor, it was Jen's gorgeous looks that had every guy (and girl) in the world crushing on her, so it's not surprising that Owen was reportedly into her.

RACHEL DID ACTUALLY DATE HER FRIENDS CO-STAR

This one takes us back, but Friends fans will always remember Joshua, the divorced shopper Rachel had to dress back when she was working at Bloomingdale's. Rachel had a major crush on Joshua (not to be called "Josh" because she "doesn't like it"). After attempting to seduce him with a cheerleading display gone wrong, Joshua ended up admitting that he was attracted to Rachel after all. Their relationship seemed strong, but Joshua had a fear of birds–whatever made Joey and Chandler think they could keep a chick and a duck?

The actor playing Josh was Tate Donovan. In 1994, he and Jen did date, although the timing was terrible. According to The Huffington Post, the pair were a couple before the actual filming of their episodes. Pretending to date when you've actually split up–that's tough.

ORLANDO BLOOM WILL TRY TO GET ANY GIRL IN HOLLYWOOD

Reputation as being a bit of a player has stuck with Orlando Bloom. The Pirates of the Caribbean actor has had a string of high-profile relationships, although he seems to have found some stability with his current lady, Katy Perry.

In 2009, The Daily Mail sent out rumors that Jen and Orlando were a secret item. They reportedly both had flights arriving at Los Angeles' LAX Airport, but were very careful not to run into each other.

Orlando and Jen apparently "gravitated" towards one another at their mutual manager's wedding, but neither Jen nor Orlando have ever confirmed the rumors. Let's hope for Katy, that this was indeed just a "Teenage Dream."

VINCE AND "THE BREAK-UP"

How well can a relationship go when the movie you're filming together is called The Break-Up? Vince Vaughn met Jennifer on the set of hilarious comedy, The Break-Up, but their off-screen relationship was the exact opposite of the script. The two were an item from 2005-2006, although there was a lot of speculation that the relationship was a re-bound for Jen. 2005 was after all the year she divorced Brad Pitt. Vince later opened up about their period together, although he kept it fairly short. Speaking to Playboy, Vince said, "She's great."

Dating someone as famous as Jennifer Aniston has its downsides, though. Vince wasn't a fan of being in the public eye, and the permanent paparazzi meant he was spending most of his time "finding ways not to be drawn into the attention."

Good thing it didn't last, then!

GERARD BUTLER SURE SUGGESTED THAT HE TRIED

And they say body language says a thousand words. In 2010, Jen was cast alongside Hollywood hunk, Gerard Butler in movie, The Bounty Hunter. Their body language on-screen was perfect, but what about the snaps of them off-screen? Neither have ever confirmed reports that they dated, but doesn't Gerard look kind of interested here?

When guys are interested in a girl, they'll find ways to be around her. That's how it goes. Not surprising then, that Gerard just about managed to get himself co-presenting a Golden Globe award alongside Jen in the same year. You tried, Gerard, but you failed.

JEN AND JOHN MAYER LASTED LESS THAN A YEAR

If you thought Orlando Bloom was walking around with "player" scrawled on the back of his jacket, that's nothing compared to John Mayer. The singer has literally dated everyone in Hollywood, including Taylor Swift and Jessica Simpson. In 2008, he tried his luck with Jen, and the innocent sweetheart said yes. Their 2009 break-up was for weird reasons, though. According to The Telegraph, Jen broke up with John because "he is obsessed with Twitter."

Despite appearing at the Oscars together, reports of John repeatedly ignoring Jen proved too much for the Horrible Bosses actress, and it's said that he straight-up ghosted her. "

I've been so busy with work. I'm sorry I haven't had time to call you back," a source told the newspaper. Like we haven't heard that one before...

IS BRAD PITT STILL TRYING?

This is literally the biggest story right now. After the biggest love triangle in Hollywood history, fans are wondering if Brad and Jen are secretly back together following his 2017 split with Angelina. This wouldn't be "first love" since Angie got in the way of Brad and Jen's 2000 marriage, so does it make sense?

In February 2018, The Sun reported that Jen was back with her ex-husband. Still, The Hollywood Reporter said that her BFF Courteney Cox had warned Jen to "leave him in the past."

Brad and Jen have more history than Ross and Rachel, and it doesn't look like "WE WERE ON A BREAK!" was on the divorce settlement. The pair haven't been seen together, but those Californian mansions have high walls, so who knows what goes on inside them...

JEN AND PAUL RUDD MADE A CUTE COUPLE

If you're recognizing that face, but can't pin it down, it's because you're looking at Friends' Phoebe Buffay's boyfriend, Mike. Paul Rudd joined later seasons of the show as Phoebe's loving and accidental boyfriend, and they even got married (despite not being able to decide how to spend their wedding money). If you're thinking that's where Jen and Paul met, think again.

Jen and Paul were a cute couple back in 1998, long before they were cast together in movie Wanderlust.

To be fair they'd had their own "wandering" and "lust" after they met, rather predictably, on the set of The Object Of My Affection. Like all of Jen's relationships though, this one didn't stand the test of time.

JOEY AND RACHEL TECHNICALLY DATED ON FRIENDS

"WE WERE ON A BREAK!" Okay, so that was the biggest phrase of the 2000s. Characters Ross and Rachel continued their "on-off" relationship on Friends, but they were "off" for quite a while. The final season saw food lover, Joey fall head over heels for Rachel, and it sure did prove interesting.

Joey had previously been known for his super casual approach to women (basically getting together with them and never calling them back), but there was something different about Rachel. Although she was pregnant with Ross' baby, Joey couldn't resist Rachel, and it turned out she felt the same way. The two were only a couple for about six weeks, but it was longer than most of Joey's relationships had ever lasted. They parted ways when Rachel realized Ross was the only guy she'd ever settle for.

CAMERON DIAZ'S MODEL BOYFRIEND BRIEFLY TRIED

Jen does seem to want to date guys with a good heart, but looking at her dating history, she sure does seem to pick the good-looking ones.

In 2007, male model Paul Sculfor reportedly gave it a shot, and according to The Daily Mail, he went on to "brag" about it five years later.

Paul isn't super famous. Alongside his modelling career, he's dabbled in acting, although he was a judge on Britain's Next Top Model. He also reportedly dated Cameron Diaz. Given how little evidence there is that he actually dated Jen though, we're sticking him in the pile of guys who "briefly tried."

DANIEL MCDONALD AND JEN HAD YOUNG LOVE

Old-school pics speak for themselves. Long before smartphones existed (and Kim K had nothing to do with her life), Jen was enjoying a young romance with actor Daniel McDonald. Daniel was nine years older than Jen, and apparently, he was "the one."

"He was my first love," Jen told The New York Times. "Five years we were together. But I was 25, and I was stupid."

Daniel guest starred on HBO's Sex And The City, plus he's been on CSI. Daniel passed away tragically in 2007 after a long illness, but it looks like Jen hasn't forgotten him.

LINDSAY LOHAN'S EX TRIED (BUT FAILED)

Yes, Jen looks very single here. You would too, if you heard that Lindsay Lohan's boyfriend had his eye on you. In 2010, rumors surfaced that Jen had a new man in her life: none other than Harry Morton, Lindsay Lohan's ex. According to Hollywood Life, Jen and Harry were both at the Sunset Tower Hotel in California, but the headline was very firm:

"Jennifer Aniston was NOT out on a date with Lindsay Lohan's ex, Harry Morton," it said. An eye witness reportedly told the media outlet that "yes, she was fixing her hair–but not in a nervous way."

Sounds about right. Jen only goes for higher-profile guys.

FERRIS BUELLER TOOK JEN OUT ON HIS DAY OFF

This one takes us way back to 1990, when NY Daily News reported that Jen had a relationship with Charlie Schlatter. The Ferris Bueller's Day Off star apparently thought that his co-star "was hot," although the report says that the whole cast had the same opinion. It's kind of twisted considering that Jennifer played Charlie's sister on-screen, but we've seen stranger things.

An on-set assistant told The Daily Mail that Jen was "lovely, kept herself to herself on-set, smoldering a bit like her outraged character." If only Hollywood stars stayed professional on the job, maybe they wouldn't have so much heartbreak (*cough* Angelina).

RUMOR SAYS AARON ECKHART GAVE IT A SHOT

Kind of ironic–the girl who can't find love keeps landing roles in movies about it. In 2008, Jen was cast with actor, Aaron Eckhart in the movie Travelling. The Daily Mail definitely had reason to suggest their relationship was "travelling," as rumors surfaced that Jen and Aaron were an item.

Aaron had personally requested Jen for the part (although who wouldn't), but did he want her for her acting skills or her girl-next-door looks? Just one year later, the two found themselves back on-set for movie, Love Happens. Seriously. Can you blame us for coming to these conclusions, or should we contact the producers and change the movie titles?

JEN'S ROCKER BOYFRIEND DITCHED HER FOR COURTENEY COX

Celebs can be a bit unpredictable with who they end up dating, and that was definitely the case for Jen back in 1995. Counting Crows frontman Adam Duritz was the apple of her eye back then, and here's a cute shot proving it. Of course, once you've got exclusive access to the cast of Friends, there's nothing to stop you shopping around.

That's exactly what Adam did, according to People, when he ditched Jen for her co-star, Courteney Cox. Remember that episode where Rachel's high-school friend asked Monica out instead of her? Welcome to TV scripts, in real life.

RIGHT NOW, JEN SEEMS TO BE DATING HERSELF

Is there literally anything more heartbreaking than the thought of a beautiful, kind, and funny actress wandering around Hollywood alone? Jen may be 49, but she's defying her age one flawless look at a time. She's got contracts like Smartwater and L'Oréal under her belt, but despite the fame and the fortune, she's very single indeed.

Jen seems to lead a pretty secluded life. She does meet up for brunch with gal pal, Courteney Cox, but it's a solo highway for the 49-year-old actress. Unless of course she's willing to let Brad back into her life, we're not sure who will be in her little black book.

Jen might need some time out after this long list, but we don't want her alone forever. Whether you're mad at Angelina or think Jen deserved what she got, hit share to see what your friends think. Of course, we also totally want to hear which of these 20 you think is Jen's best fit–unless of course, you can think of someone else.