Relive Brad Pitt and Jennifer Aniston's Romance, From the '90s to Their "Flirtatious" Current Relationship

Brad Pitt and Jennifer Aniston had one of the most buzzed-about relationships in Hollywood history. From their '90s dates (the matching looks!) to their five-year marriage and eventual split, it's the couple we can't stop analyzing. But in 2020, there's actually reason to unpack this dynamic. They'll be in the same room again this awards season for the Golden Globes and SAG Awards (he's nominated for Once Upon a Time in Hollywood, she for The Morning Show). Plus, after reconnecting at Aniston's holiday party last month, an Us Weekly source says the former husband and wife have a "wonderful connection that might seem flirtatious at times." Below, a look back at the couple's fashion when they were together and what happened to them after they broke up...then became friends again, years later.

Tentative fashion, two ways: her belly peek, his goatee at the premiere of Fight Club.

Who is she?

Power couples love to trade lip colors.

"I told him that contrast collar was a little much with the pinstripes, but he never listens..."

"Is that Danny DeVito?"

Brad blocks Jen as she tries to dodge her hairstylist's old assistant, who is dying to take her back to the Rachel.

It's not easy wearing a man choker, but somebody's got to do it.

Here we reach the stage where they dress like their favorite beverage. Him, cafe au lait, heavy on the lait. Her, an extra thick vanilla soy milkshake.

Ken and Barbie, millenium style.

"The last thing I need is David Schwimmer telling me how to emote..."

Brad as a proto Justin Timberlake; Jen tolerating.

Happy New Year from the guy that works at your video store and his most loyal customer.

"Glasses on or glasses off?"

Jen with the missing member of Blue's Traveler.

"The things we do for love," Jen thinks, recalling the long hours she spent sewing an American flag patch on her husband's best acid-washed jeans the evening before.

TFW you asked him to trim his beard but he wore a satin button-up instead.

Renewing their vows at the Emmys.

His and hers early aughts ennui.

"Told you my nipples wouldn't show through my gauzy chain-printed button-up."

"You sure I wouldn't make a good Chandler Bing?"

As long as Jen's body double keeps that swath of bangs down on her face, and the two stand just like that, the real Jennifer Aniston can skip Brad's premieres and stay home and watch Veronica Mars undetected.

Hair envy.

"Just keep looking at me and nobody will notice your blonde went a little brassy in the pool, honey."

Jen delivering three boxes of Kleenex to Brad on set.

Renewing their vows (again) at the Emmys (again).

Get you a partner who...can identically mirror your facial expression? It would be (deep breath) their last major red carpet appearance together.

Alas, America's Golden Couple is not meant for forever. The pair releases the following statement to People regarding their split:

"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. We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months."

After meeting on the set of Mr. & Mrs. Smith in 2004, rumors of a relationship between Pitt and Angelina Jolie arise in April 2005. The pair is spotted playing with Jolie's young son Maddox on a beach.

Then comes a now infamous W magazine spread featuring Brangelina looking very domestic months after Pitt's split from Aniston. Aniston later tells Vanity Fair that her ex-husband was "missing a sensitivity chip." By October, their divorce is finalized.

Pitt and Jolie are married in France after nearly a decade together. She wears a Versace dress with veil that includes sketches by her children with Pitt—Maddox, Pax, Zahara, Shiloh, Knox, and Vivienne.

As for Pitt's status with Aniston? In 2009, he tells W Magazine, “We still check in with each other. She was a big part of my life, and me hers. I don’t see how there cannot be [that]. That’s life, man. That’s life.”

Aniston marries Justin Theroux after four years of dating. That same year she updates The Hollywood Reporter on her relationship with Pitt:

"We’re not in daily communication. But we wish nothing but wonderful things for each other. Nobody did anything wrong. You know what I mean? It was just, like, sometimes things [happen]. If the world only could just stop with the stupid, soap-opera bullshit. There’s no story. I mean, at this point it’s starting to become—please, give more credit to these human beings."

Jolie files for divorce from Pitt after two years of marriage. She cites irreconcilable differences and requests physical custody of their six children. One of her attorneys releases the following statement concerning the filing: "This decision was made for the health of the family. She will not be commenting, and asks that the family be given its privacy at this time."

As of October 2019, the couple's divorce has reportedly not been finalized.

A source tells Us that the former exes have "been texting" after Pitt found Aniston's phone number through “a tangled web” of contacts so he could wish her happy birthday on February 11. Reportedly, Pitt "has confided in Jen," the source adding, “Brad told her he’s having a hard time with his split and they exchanged a few texts reminiscing about the past.”

After two years of marriage, Aniston and Theroux announce their split. In a statement the couple shares:

"In an effort to reduce any further speculation, we have decided to announce our separation. This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship."

A source tells Us Weekly that Theroux reportedly "stumbled upon old Post-it notes Brad had written,” during his marriage to Aniston, continuing, “Sweet little Post-its like, ‘You looked nice tonight’ or ‘Miss you already.’” The insider adds, “Jen assured him they weren’t a big deal, but Justin wasn’t thrilled … Justin had moments of insecurity like that.”

However, a source clarifies to People that reconciliation for Aniston and Pitt is not in the cards. “They aren’t in regular contact, beyond an occasional text back and forth to wish each other the best when there’s been a new project or big event,” the source explains.“They broke up, and they did it because they had serious issues. They’re not stupid. They remember why it didn’t work.”

People reports that Pitt's among the guests at Aniston's star-studded 50th birthday party at the Sunset Tower Hotel in Los Angeles.

“Brad, for long, was a very important part of Jen’s life. She debated back and forth with friends if she should invite him,” a source says. “She was very happy that he showed up. Many of his close friends were at the party too.” The insider continues that Aniston “didn’t really pay any special attention to Brad. They hugged and chatted for a bit, but Jen was busy making sure all of her other guests had an amazing time."

Meanwhile, a Pitt source tells Entertainment Tonight that Pitt “wanted to support” Aniston since the two have “been friendly” in recent years. Following his addition to the guest list, the source says Pitt "happily" chose to participate.

Amid renewed interest in the relationship (but did it ever really wane?), a source tells all to Us Weekly about the former couple's friendship. Per the insider, Pitt and Aniston began talking in May 2016. “Brad contacted Jen after her mom died, and she was touched that he knew what a difficult time it was." The source continues, "He asked for Jen’s forgiveness a long time ago, and she gave it."

Entertainment Tonight reports that Pitt was in attendance at Aniston's holiday party. “Brad Pitt arrived at Jennifer Aniston’s holiday party a little after 7 p.m. on Saturday,” a source says, adding, “He was among the first to arrive and the second-to-last guest to leave around 11 P.M.” Pitt was on a guest list alongside his other ex Gwyneth Paltrow, Lisa Kudrow, and Reese Witherspoon.

As for any awkwardness between these exes heading into award season, a source tells Us Weekly there's no drama. “A reason Brad and Jen get along so well now is that they’ve agreed to bury the past and not analyze what went wrong. They’re both looking forward, not back," the source explains. “He’s taken responsibility,” the insider continues. “He’s tried to make amends. He didn’t realize the magnitude of the hurt he caused Jen at the time. He was so swept up in Angelina Jolie, he couldn’t see outside that tunnel.”

So where do the former husband and wife go from here? Another Us Weekly source speaks on the "wonderful connection that might seem flirtatious at times" between the two. "They dig each other’s sense of humor and have an infectious energy when they’re together, but they insist things are purely platonic and nothing more than that," the source continues.