Juicy Details About Jennifer Aniston’s Past Relationships You Didn’t Know About

Jennifer Aniston is most well-known for her role as Rachel Green on Friends but she has made quite the impact on films, television, and American pop culture. Also known as America’s Sweetheart, Aniston’s personal love life has been the object of media attention for many, many years. Her dating history has led her to the love of her life and her husband, Justin Theroux, but this article will revisit all of the juicy details about her former loves.

Adonis Tsilimparis

Jennifer Aniston’s first boyfriend (at least as far as the public knows about) in 1990 has spoken out about his fleeting high school relationship with the Hollywood star. She might have dated several of the world’s most desirable men (like Brad Pitt and John Mayer) but a musician named Adonis Tsilimparis was the first man to pucker up with this desirable actress.

Adonis Tsilimparis

About 30 years ago, her first relationship was a seventh grade romance between two 12-year-olds. It is still fresh in his memory, and to this day, he even has a Valentine’s Day card to prove it. “Dear Adonis,” Jennifer wrote. “Love & Friendship Always. Jennifer A.” How sweet!

High School Romance

Now 30 years later, Tsilimparis is working as an author of musical scores for TV and film. But back in the day, Tsilimparis gushed that the two youngsters used to sneak behind a school staircase to “make-out.” And Tsilimparis remembers Aniston fondly. “She was very open, very, very sweet. She was very, very loving, and she had a very big heart.”

High School Romance

And the story of their brief relationship gets a little juicy. Although he had tried, Tsilimparis hadn’t got any further than kissing with Aniston. “I tried. But she didn’t let me…We used to go to the back stairs at school at lunchtime and make out,” he admitted. He also admits to loving her. “She was just goofballs…But that’s why I loved her. Total clown, very lovable and that’s why everybody liked her,” Adonis said of the Hollywood star. But like many childhood relationships, their relationship quickly ended.

Daniel McDonald

Unfortunately for Ms. Aniston, she has also had love lost. Jennifer Aniston spoke in 2015 about her now-deceased first love, Daniel McDonald. But the love story got a bit more complicated because the man’s widow has a different story to tell.

Daniel McDonald

Aniston first mentioned her late ex in an interview with The New York Times, and said, “He was my first love — five years we were together,” she said without naming McDonald, who later died. He had brain cancer. She elaborated by saying, “He would have been the one. But I was 25, and I was stupid. He must have sent me Justin [Theroux] to make up for it all.”

Love Lost

There were few clues to the man’s identity, but who he was became confirmed when his widow came forward. Mujah Maraini-Melehi addressed Aniston’s revelation, and decided to tell her own story about Aniston’s relationship with her late husband, Daniel McDonald.

Love Lost

“Daniel and Jennifer had a relationship over 20 years ago, when they were both still very young. She made a life choice, but so did he,” Maraini-Melehi said. “I am sorry that Jennifer did not realize the treasure that was Daniel when she had the chance, long before he and I met and long before he died. It pains me to read the headlines that allude to her losing him tragically when in fact she was not present during his long and difficult illness.” Ouch. McDonald died at the age of 46 in 2007.

Charlie Schlatter

Charlie Schlatteris an American actor, voice actor, and writer. He has also appeared in numerous TV series and films. He is probably best known for playing Dr. Jesse Travis. You know, the handsome resident student of Dr. Mark Sloan (played by Dick Van Dyke).

Charlie Schlatter

Schlatter was also on over five seasons of the CBS series Diagnosis: Murder, and starred in big screen comedy 18 Again!, opposite George Burns.At the start of her career, Jennifer Aniston had an eye for dating actors. Back in 1990, the then 21-year-old Aniston allegedly had a “torrid” affair with her Ferris Bueller co-star Charlie Schlatter.

Interesting Encounter

The ill-fated TV show, which ran for just one season, from 1990 to 1991 was based on the 1986 John Hughes film. Aniston starred as Jeannie Bueller, the older sister of Ferris, played by Schlatter.Her former costar stated, “She was lovely, kept to herself on the set, smoldering a bit like her outraged character.”

Charlie Schlatter 2

He also said, “She was a brunette then, with none of Rachel Green’s bob or self-possession.” He then went on to reveal her brief affair with her co-star. Everyone on set thought she was hot, including Schlatter. She had a brief, romance with Schlatter while playing his older sister. “To we immaturions on the show, this seemed extra-hot. Like performative incest,” he said. Um…gross?

Jon Stewart

Jon Stewart is an American writer, actor, producer, director, comedian, media critic, and former television host (just to name a few claims to fame!). He was the host of the popular television show, The Daily Show, a satirical news program on Comedy Central. His hosting gig lasted from 1999 until 2015.

Jon Stewart

Stewart started as a stand-up comedian. He soon branched into television as host of Short Attention Span Theater. He went on to host his own show on MTV, The Jon Stewart Show and You Wrote It, You Watch It. He also participated in film roles as an actor, but has done few cinematic projects since being on The Daily Show.

Just a Bunch of Jokes

But before Aniston’s flings with Pitt, Vaughn and Mayer, there was Stewart – Jon Stewart. Jennifer Aniston visited The Daily Show and Stewart reminded her that they’d shared a romantic Italian meal in New York City more than a decade ago. But their recollections of the evening were somewhat conflicting.

Just a Bunch of Jokes

Stewart stared by saying, “I asked you out, and it was lovely. I remember you brought so many of your friends. And I remember thinking, ‘She’s so excited to be on a date with me, she wants me to get to know her posse.’” But Aniston saw things differently. “If I remember correctly, wasn’t it sort of like, ‘Hey, a group of us are going out, do you want to join?” she asked. Oh, burn! Stewart finished with saying, “You were lovely then and lovely now.” Adorable!

Adam Duritz

Adam Duritz is the Counting Crows frontman. He is an American musician, songwriter, record producer, and film producer. He is a founding member of Counting Crows and principal composer of their catalog of songs. Prior to being famous, Duritz wrote songs and sang for a few San Francisco Bay Area bands in the 1980s.

Adam Duritz

Adam Duritz is one of rock ‘n’ roll’s most cinematic songwriters. He writes thoughtful, tortured lyrics. He has the ability to paint scenes with pigments of human emotion. Duritz can summon a sensation usually confined to a single word, which makes him an extremely talented and gifted musician.

Sparks Turned to Fizzle

Duritz was very popular and big on the scene in the early ‘90s; he made a huge splash in the music scene. Aniston and Duritz dated for a short period in 1994 and after their split in 1995, he transferred his affections to her Friends co-star Courteney Cox. Drama!

Sparks Turned to Fizzle

Apparently, the romance was not as heated as previously thought. Duritz openly admitting that they never slept together! Regardless of how their relationship was or how it ended, it must have felt like a right slap in the face to break-up and then to see her ex be romantically involved with such a close friend.

Tate Donovan

Tate Donovan is an American actor and director. He is known for portraying Tom Shayes in Damages and Jimmy Cooper on The O.C. He is also known as the voice of the title character in the 1997 Disney animated film Hercules. And if you are a video game fan, you may recognize his voice in the Kingdom Hearts video games.

Tate Donovan

Donovan also had supporting roles in films, such as Good Night, and Good Luck and Argo. Donovan also played Brian Sanders in Hostages and White House Chief of Staff Mark Boudreau in 24: Live Another Day. He has been a guest star in a number of popular television series so you have probably seen him at one time or another.

Joshua

If you are a big Friends fan, then you will remember Joshua. Rachel and Joshua dated soon after she admitted she was infatuated with him. Well, there is a real-life love story behind this on-screen love. Jennifer Aniston dated Tate Donovan, who played Joshua on Friends, for three years beginning in 1994. They actually got engaged, too!

Joshua

Unfortunately for him, he had to star as her love interest on the show, while the two were ending their real-life relationship. Donovan has discussed how uncomfortable the situation was for him and how he feels about Aniston now saying that back then, it was incredibly difficult, but now, he is happy they have both found love elsewhere. The experience of starring as her love interest “was horrible!” He adds, “I remember just getting back to my dressing room and just weeping […] It was tough! Can you imagine?” What a nightmare!

Paul Rudd

Paul Rudd is a popular American actor, comedian, writer, and producer. He is known for his various starring roles over the last 20 years. From the comedy films Clueless, Wet Hot American Summer, Anchorman: The Legend of Ron Burgundy, and The 40-Year-Old Virgin to Halloween: The Curse of Michael Myers and several recent box office hits like Knocked Up, Role Models, and I Love You, Man, odds are you have probably seen Rudd in a movie or two.

Paul Rudd

Rudd received a star on the Hollywood Walk of Fame on July 1, 2015. But after filming The Object Of My Affection in 1998, Paul Rudd became the object of Jen’s affection. When things ended, they worked together again on the set of Friends. Rudd played Phoebe’s boyfriend (and then husband) Mike.

Friends ’til the End

Rudd was so lovable when he played Phoebe’s husband on Friends! Well, turns out he’s actually that delightful in real life, too (but that honestly isn’t a surprise!). He was awarded the title of “The Most Loveable Movie Star On The Planet” by Entertainment Weekly.

Friends ’til the End

But in terms of their relationship and how it ended, it is obvious there is no bad blood. In 2011, Jen revealed the famous pair were together “when we were, like, 12.” The pair still has fun reuniting professionally, collaborating on films and enjoying each other’s company—as friends. They even enjoy joking about their history of regular make-out sessions (professionally, of course)!

Brad Pitt

If you don’t know who Brad Pitt is, then you might be living under a rock. But we’re happy to refresh your memory! He is an American actor and producer. Pitt has received multiple awards and nominations and even an Academy Award as producer. But way back when in 1991, Brad Pitt first gained recognition as a cowboy hitchhiker in the huge box-office hit Thelma & Louise.

Brad Pitt

His greatest commercial successes have been his recent films such as Mr. & Mrs. Smith, Troy, and World War Z. Pitt received his second and third Academy Award nominations for his leading performances in the 2008 film, The Curious Case of Benjamin Button and in the 2011 film Moneyball. He produced the moving films The Departed and 12 Years a Slave, which he won the Academy Award for Best Picture for both films.

Hollywood’s Golden Couple

Pitt has been cited as one of the most influential and powerful people in the American entertainment industry. He has also been awarded the world’s most attractive man, by various media outlets, but in terms of accolades, that seems to be the lowest priority. His personal life is also the subject of wide publicity.

Hollywood’s Golden Couple

Brad and Jen reportedly met back in 1998. Their agents set them up on a blind date and it looks like the blind date worked! The couple happily dated for more than two years before deciding to get married in 2000. We all thought they were perfect and destined for happiness. They were even dubbed “Hollywood’s golden couple.”

The Break-Up Heard around the World

Back in the day, Brad and Jennifer were the perfect Hollywood couple. They were so sweet together and it didn’t hurt that they were two of the most attractive human specimens walking our planet. He seemed like the perfect man; that is, until he decided to cheat and to leave his wife for Mr. & Mrs. Smith co-star Angelina Jolie.

The Break-Up Heard around the World

When the break-up was official, American hearts were crushed along with Aniston’s. They were America’s hottest celebrity couple for five years. Despite their divorce in 2005 and Brad’s now failed relationship with Angelina Jolie, Brad and Jen are still friends

Vince Vaughn

After her relationship with Pitt ended tragically, she “rebounded” with Vince Vaughn after they met on the set of their film, The Break Up (ironic, yes!) After a year, the pair went their separate ways. But their break-up didn’t seem as dramatic as their film. They both spoke very fondly of each other.

Vince Vaughn

“You know, she’s great,” Vaughn said. “For me personally — and I think most well-known actors who are together feel this way — I never enjoyed the paparazzi side of it. You like someone and you’re spending time with them; that’s separate and that was all fine. But I really spent most of that time finding ways not to be drawn into the attention.” Aniston said, “I call Vince my defibrillator. He literally brought me back to life. My first gasp of air was a big laugh! It was great. I love him. He’s a bull in a china shop. He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course.”

Paul Sculfor

Jennifer Aniston quietly dated Paul Sculfor in 2007. He is a British model has a hint of the Pitt look about him, which definitely got people talking after they were first spotted out together over Memorial Day weekend in 2007. They seemed to be pretty fond of each other but their relationship ended up being very brief.

Paul Sculfor

Sculfor, who now lives in Los Angeles and works for New York Model Management, said of Hollywood relationships, “It’s hard keeping a girlfriend in this business – you end up conducting your relationship on the phone.” Soon after they broke things off, Sculfor was spotted out with Cameron Diaz.

“The One” — Justin Theroux

There were a series of “rebound” type relationships after Brad Pitt. From, a couple of dates with Orlando Bloom and a flirty relationship with Owen Wilson, Aniston got to enjoy her single life. She also dated Aaron Eckhart in 2008 and notorious bad boy John Mayer before catching the eye of Gerard Butler. But none of these relationships lasted or amounted to anything.

“The One” — Justin Theroux

Jennifer Aniston finally found Mr. Right with screenwriter Justin Theroux. After a year of dating, he popped the question on his birthday — it looks like he wanted to get the best birthday gift for himself! After a somewhat lengthy engagement that sparked a lot of gossiping the couple married in August 2015. They tied the knot in front of friends and family at a surprise wedding at their home.