Brad, Justin & John! Jen Aniston's Relationship Scandals Exposed As Star Turns 50

Jennifer Aniston just turned 50 — and she's single!

Though she reunited with ex-husband Brad Pitt at her birthday bash last weekend, the Friends star will face the milestone on February 12 alone, after her marriage to Justin Theroux failed and many other relationships, such as high-profile romances with John Mayer and Vince Vaughn, also flopped.

As RadarOnline.com has previously reported, a source said America's sweetheart feels embarrassed about her sad status.

“She never thought she would be single at 50, and even though she’s outwardly insisting she’s fine about it, deep down she’s humiliated,” a source close to the ex-Mrs. Pitt told RadarOnline.com exclusively.

“Jen thought she would be settled into a new relationship by now,” the source added about the actress who has also never had any children.

After her shocking divorce from Pitt, the Horrible Bosses star suffered a second broken marriage, to Theroux.

Aniston and Theroux split just before her 49th birthday in 2018. Since then, she reportedly hasn't been in a relationship.

Scroll through RadarOnline.com's gallery for more on the history of the men Aniston has loved and lost as she faces being all alone at 50.

Justin Theroux: Aniston got engaged to writer/actor Theroux in 2012 and they wed in 2015. But it was a short union as they reportedly separated in late 2017. The two officially announced their breakup in Feb. 2018, just before Aniston turned 49. According to an Us Weekly source, Aniston and Theroux have barely spoken since the split. The actress insisted to InStyle that she was “not heartbroken” after her divorce from the actor.

Brad Pitt: In one of the biggest A list Hollywood weddings of all time, the Friends star married the movie hunk on July 29, 2000. But Pitt reportedly cheated on her with sexy Angelina Jolie. Aniston and Pitt divorced in 2005, and he went on to have a family with Jolie, whom he finally married in 2014. However, Aniston had the last laugh as Pitt and Jolie separated in 2016, and are still battling in a bitter divorce.

Vince Vaughn: In one of her most publicized relationship fails, post-Pitt Aniston split from her The Break Up movie co-star after months of dating. Aniston and Vaughn spent major amounts of time apart and things fizzled out in fall 2006. "He was lovely and fun and perfect for the time we had together….And it sort of ran its course,” she later told Vogue. Vaughn, who admitted he didn't like the spotlight that came with Aniston, went on to marry realtor Kyla Weber and they have two children.

Adam Duritz: The Counting Crows front man commented about dating Aniston in 1995, "We never even slept together." After they split, the rocker dated her BFF and Friends co-star, Courteney Cox!

Tate Donovan: The actor dated Aniston from about 1995 to 1997, and their relationship was "breaking up at the time" he did a brief guest arc on her show Friends. Donovan told Us Weekly he was "dying inside" when they acted together on the hit sitcom. They were engaged but it didn't last -- and she fell for Pitt in 1998.

Paul Sculfor: Jen was rumored to have romanced the sexy British model for a couple of months in 2007. He then moved on to another A list actress, Cameron Diaz.

Orlando Bloom: Rumors ran wild in 2007 that Aniston was dating the Pirates of the Caribbean actor. It was never confirmed and never denied.

Owen Wilson: In spring 2008, there was speculation Aniston was cozying up to her Marley & Me co-star. Wilson reportedly made the star laugh.

Gerard Butler: It was reported that Aniston had hooked up with her co-star on the 2010 movie The Bounty Hunter. The rugged Scottish actor and Aniston were spotted holding hands at dinner in New York. But Aniston's publicist denied the claims at the time and neither star confirmed the romance. RadarOnline.com sources say the ex-lovers still talk.

Harry Morton: In what PEOPLE called a "summer hookup" in 2010, Aniston shared some dates with the handsome restaurateur who was twelve years younger.