ByVaria Fedko-Blake, writer at
Staff Writer at Moviepilot! [email protected] Twitter: @vfedkoblake
Varia Fedko-Blake

Jennifer Aniston has experienced her fair share of mishaps when it comes to relationships. Following the disastrous end to her marriage to Brad Pitt, the Friends star unashamedly went on to date a great selection of gorgeous men in her attempt to find 'The One.'

Since my profile on her life struggles the other day, I thought it would only be fair to create a much more comprehensive profile on some of her colorful dating history. Bear in mind, that some minor relationships have been skipped out...

Here we go!

1. Adam Duritz

When? 1994

What happened? Jennifer went out with the Counting Crows frontman for a short period in 1994, before he went on to date her co-star and best-pal Courtney Cox. Apparently, the romance was not as heated as previously thought, with Duritz openly admitting that they never slept together.

Still, it must have felt like a right slap in the face to break-up and then to see her ex-lover be romantically involved with such a close friend.

2. Tate Donovan

When? 1995 - 1998

What happened? The pair went out for almost three years and were actually engaged before finally calling it quits.

As Donovan did a stint on Friends, he also recently revealed that that working with her on set was absolutely awful. During the filming, they were both in the process of breaking up and 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.

3. Paul Rudd

When? 1998

What happened? Funny man Paul Rudd and Jennifer met during the filming of The Object of My Affection and were in a relationship that lasted around a year. Since the breakup, they have remained fantastic friends and even starred in Wanderlust together.

In an interview with GQ, when asked if it was weird to kiss on screen as longtime friends, they laughed it off saying "we've made out for decades."

I always knew Paul was one of the good guys.

4. Brad Pitt

When? 1998 - 2005

What happened? When I think about this one, it almost brings a tear to my eye. Back in the day, Brad and Jennifer were the perfect Hollywood couple and possibly two of the most attractive human specimens walking our planet. For Jen, he seemed like the perfect man: He was a wonderful person, had the face of an angel, he had rock hard abs and was incredibly talented. Indeed, Brad ticked all the boxes... that is, until he decided to cheat and to leave his wife for Mr. & Mrs. Smith co-star Angelina Jolie.

Our hearts were crushed along with Jen's. Safe to say, this is a break-up I will NEVER get over.

5. Vince Vaughn

When? 2005 - 2006

What happened? We really hoped that Vince Vaughn would be the man to mend Jen's broken heart and pick her up from the bottomless abyss that she was mercilessly thrown into. Ironically, the two met on the set of The Break-Up but unfortunately after a year or so of dating, and many engagement rumors, they decided to... break up...

Check them both out in the movie trailer:

6. Paul Sculfor

When: 2007

What happened? Jennifer dated British model (and former brick-layer!) Paul Sculfor for a few months and honestly, no matter how hard I try, there is really not much to report about their fling.

I just decided to include him in the list because he is super fit! (He also strangely looks a bit like Brad?)

7. John Mayer

When: 2008 - 2009

What happened? Jen clearly wasn't forewarned when she agreed to go out with notorious womanizer John Mayer. Yet, for a while it seemed that the lovebirds would make it, with Mayer reportedly looking to purchase an 18-carat diamond ring for her that would have set him back millions. Yet, the relationship was a turbulent one, not surprising really considering he is a bit of a dick to all his girlfriends (Taylor Swift even wrote a song about it entitled 'Dear John')!

Since the break-up, Mayer admitted to Rolling Stone that:

"I'm the asshole. I burned the American flag. I basically murdered an ideal [...] I've never really gotten over it [...] It was one of the worst times of my life."

Should have thought about that before you went and crushed poor Jen's heart, shouldn't you have John?

And finally...

Just as we were ready to lie down and keel over for lack of hope, Jennifer finally found her Mr. Right.

Justin Theroux

When? 2011 - present

What happened? Despite meeting years prior, the passionate romance that blossomed between Jennifer and Justin Theroux began on the set of Wanderlust. Speaking of her first impression of him, she said:

"I thought he was very sweet and he was always very nice. But I remember thinking he was very dark. At first you think he could be like a serial killer, but he is actually the nicest person in the world."

Since sparking the initial connection (and finally perhaps realizing she's attracted to... serial killers?), the whirlwind romance has led to great happiness for our unlucky-in-love starlet. Currently, she has been engaged since 2012 with the wedding set for the near future.

We salute you Jen for finally finding 'The One' and we wish you the best of luck!


Do you think Jen has finally found The One?



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