Skip to main content

Jennifer Aniston has been in the spotlight since the ’90s when she skyrocketed to fame on the hit sitcom Friends. From her marriages to her wellness regime, people have always been fascinated by the actor’s life. Though she has kept many things to herself, the Horrible Bosses star has given the world some insights into her personal life.

In fact, we know that her favorite Valentine’s Day gift didn’t come from Brad Pitt or Justin Theroux.

Jennifer Aniston
Jennifer Aniston | Jason Merritt/Getty Image

Inside Jennifer Aniston’s dating history

Though we know all about Aniston’s whirlwind romance with Pitt that ended amid his affair with Angelina Jolie and her short-lived marriage to Theroux a few years ago, The Morning Show star has been connecting to a lot more high profile men than that.

In the ’90s, Aniston dated Paul Rudd and Tate Donovan, and she was even linked to her Friends co-star Matthew Perry in the early 2000s. However, neither actor has confirmed or denied a romance.

Aniston has also been linked to Gerard Butler, Vince Vaughn, and John Mayer. However, she says the one that got away was her first love, actor Daniel McDonald. The pair dated from 1990 to 1994. “He would have been the one, but I was 25, and I was stupid,” Aniston reportedly said via The Sun. McDonald died from a brain tumor in 2007.

Jennifer Aniston dated Tate Donovan for years

Aniston began dating Donavoan in 1995, just as her fame was skyrocketing because of Friends. The O.C. alum had previously dated Sandra Bullock, but he was completely unprepared for the mania surrounding Aniston.

“Literally, our second date, there were video cameras everywhere, and I was like, ‘I’m out of here,'” he told People at the time.  The pair split just a month later, but later rekindled their romance, dating for two years. In 1997, he even spoke briefly about marrying Aniston.

“I definitely want to get married; she definitely wants to get married. There are no proposals or anything, not yet, but we definitely think about it,” he told People.

However, the pair eventually called it quits, but not before Donovan had a recurring role on Friends. “The only bummer was Jennifer and I were breaking up at the time,” he recalled to Us Weekly in 2018. “And so that was tricky to sort of act, and act like we are just meeting each other, and falling in love, or whatever, interested in each other, when we’re sort of breaking up. That was just tough.”

Related

The 1 Unhealthy Snack Jennifer Aniston Said She’s ‘Powerless’ to Resist

Jennifer Aniston’s favorite Valentine’s Day gift was adorable

Though their romance did not withstand the test of time, the Along Came Polly actor’s favorite Valentine’s Day gift is still one that Donovan got her while they were dating in 1996.

The actor had just completed a scene for Friends and went back to her dressing room, expecting to find Donovan. Instead, she found a  9-week-old puppy named Enzo.

“Then I opened the door, and this little puppy with a ribbon on poked his head out,” she said via InStyle. We can understand why this is still the actor’s favorite Valentine’s Day gift.