Jennifer Aniston continues to steal every man’s heart, even at the age of 56. Back when she was playing Rachel Green, things were no different. Aniston had dated her fair share of men over the years, including but not limited to the late Daniel McDonald, Vince Vaughn, and Justin Theroux, with whom she was engaged.
Currently, the actress is in a loving relationship with wellness coach, hypnotherapist, and author Jim Curtis. He is reported to be seven years younger than Aniston, but the age gap isn’t coming in the way of their budding romance.
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While Aniston and Curtis’ relationship continues to bloom, let’s take a quick look at every FRIENDS actor she has dated in the past, including Brad Pitt!
1. Tate Donovan – Joshua Burgin
Known for roles in projects like The O.C., Hercules, Love Potion No. 9, and so much more, Tate Donovan was in a relationship with Aniston from 1995 to 1998. As per Donovan, he initially had no idea who the actress was when they first met through mutual friends. He told PEOPLE (via US Weekly), “I’d never seen Friends!“
When he did find out who she was, though, Donovan was hesitant to take things further with the actress. Why? Because he was just healing from his breakup with Sandra Bullock, following a four-year-long relationship, a relationship that left his Love Potion No. 9 co-star with trust issues.
He was simply not ready to fall into yet another high-profile romance. He said, “Literally, our second date, there were video cameras everywhere, and I was like, ‘I am out of here.” For whatever reason, Donovan ended up giving it a shot a few weeks later. After all, who can resist Aniston?
Their relationship was pretty serious. On their first anniversary, they gifted each other Irish commitment rings. He even surprised her with a puppy, Enzo, on their first Valentine’s Day together. Needless to say, the couple was in love.
Eventually, the end of their relationship came, and it couldn’t have come at a worse time – Donovan landed the role of Joshua in FRIENDS. Moreover, he was playing a character that Aniston’s Rachel was head over heels for. Despite the awkward situation, Aniston and Donovan kept their split a secret from the producers.
Donovan told The Independent in 2024, “I’d been dating Jen for years, and I knew the cast…Then Jen and I broke up, but we didn’t really tell anyone.” As for what it was like working together, the actor stated that it was “tough” to say the least.
Comparing it to high school, Donovan recalled,
It was very tough. Everyone was so supportive, but it was hard. It’s like going to class when you’re in high school and you’ve broken up with the girl who you sat next to and… argh, it’s tough. But it makes you a pro – it’s like, OK, we got over it. Nobody knows; the audience isn’t gonna know; the audience is gonna think just the opposite. When I look back on it, I’m like, ‘Wow, good for you, man. That was pretty good’.
Despite the breakup, neither Donovan nor Aniston had anything negative to say about the other. In fact, she told PEOPLE (via eonline) in 1997 that her former beau was “so real, so honest, so kind and considerate. He’s all these things meshed into one perfect guy.“
2. Paul Rudd – Mike Hannigan
Rachel Green dating Phoebe Buffay’s husband? Now this may be a shocker to some. Aniston and Paul Rudd were rumored to have been romantically involved at some point in their lives. According to Nicki Swift, they first met while filming their 1998 rom-com, The Object of My Affection.
As they played the roles of two friends, Nina and George, who develop romantic feelings for each other, those around them couldn’t help but question if their chemistry went beyond the script.
The rumors claimed that their connection was simply too strong to ignore, which is why they decided to get into a relationship soon after meeting. Aniston once reportedly joked about the rumors, stating that they were “together when we were, like, 12.“
Last year in April, Aniston wished him a happy birthday through her Instagram story, calling him an “ageless freak“:
Rudd and Aniston may or may not have been a thing in reality, but they sure had chemistry that couldn’t be overlooked. After The Object of My Affection, they starred together in Wanderlust (2012).
3. Brad Pitt – Will Colbert
What more could we say about Brad Pitt and Aniston that you already don’t know? After meeting for the first time in 1994, Aniston and Pitt had their first date in 1998. It didn’t take long for the couple to fall in love, so much so that they got engaged the very next year, in November.
As per PEOPLE, Pitt spent seven months helping design the stunning diamond-and-platinum engagement ring by Silvia Damiani that sat on Aniston’s finger. Finally, they tied the knot on July 29, 2000, surrounded by 200 of their friends, family, and co-stars.
In November, Pitt made his FRIENDS debut as Will Colbert, the heartthrob co-founder of the I Hate Rachel Green Club. They had a good run before they finally announced their decision to split in 2005.
The actors said in a joint statement,
We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration.
They promised to remain friends with nothing but “great love and admiration” for each other. Before their split, the relationship had been plagued with rumors of infidelity on his part. Reports claimed that Pitt had been unfaithful to Aniston with Angelina Jolie.
While no one ever publicly confirmed the allegations, Aniston’s co-star Courtney Cox told Vanity Fair, “I don’t think he started an affair physically, but I think he was attracted to her.” She added,
“There was a connection, and he was honest about that with Jen. Most of the time, when people are attracted to other people, they don’t tell. At least he was honest about it. It was an attraction that he fought for a period of time.”
Did Jennifer Aniston and David Schwimmer Ever Date?
With the kind of chemistry Aniston had with David Schwimmer on FRIENDS, no one would blame you if you thought the two were a thing in real life, too. However, as it has been confirmed many times, Aniston and Schwimmer’s romance was limited to Ross and Rachel.
It turns out, though, that the actors had a crush on each other in the early seasons of the sitcom. On Live with Kelly and Mark (via Grazia), the host said to Aniston, “You and David in the early years had a crush on each other.”
She replied, “Yes, we did. We just let it play out on TV…Sure enough, the first time we kissed was in that coffee shop. So, we just channelled all of our love and adoration for each other into Ross and Rachel.“
They even admitted their feelings on the 2021 reunion special, where Schwimmer stated, “The first season I had a major crush on Jen.” He added that nothing ever happened between them because at least one of them was always in a relationship with someone else. In his words, “We never crossed that boundary. We respected that.“
He did admit that they would often “cuddle on the couch” during breaks. On the other hand, their co-stars could notice what was going on between them.
While Aniston seems to be in a happy relationship now, which of her FRIENDS‘ lovers do you think she had the best chemistry with? Let us know your thoughts in the comments section below.
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