The truth about Bill Hader and Rachel Bilson's relationship

We bet you never saw this one coming, huh? Summer Roberts and Stefon spending half of 2020 as Hollywood's hottest couple. Sorry, we meant Rachel Bilson and Bill Hader. The former starlet of The O.C. and the Barry star fueled dating speculation for weeks before making their grand entrance at the 2020 Golden Globe Awards. (Billson? Rachader? Billrach? We're just spitballing on ship names here, please be patient.)

With Bilson's dating history including Hayden Christensen and her co-star on The O.C., Adam Brody, this surprising couple didn't seem like the perfect match at first glance. However, they go way back. How far back, you might ask? Well, their history is what you might expect from a comedian and the former star of a teen drama: equal parts hilarious, complicated, messy, and dramatic. 

While all of us shipped this adorable duo, Bilson and Hader, unfortunately, decided to go their separate ways in July of 2020 — a mere six months after going public. Although People broke the shocking news, both stars are staying mum on the subject at the time of this writing. While we're still recovering from this tragic celeb breakup, let's take a trip down memory lane and relive all the goss that was Rachel Bilson and Bill Hader's relationship.

Let the relationship rumors begin

On Dec. 22, 2019, TMZ published photos of Bill Hader and Rachel Bilson grabbing coffee in his hometown of Tulsa, Okla. "There have been rumors for a while the celebs were dating," the gossip rag claimed at the time. "And this seems to confirm they're pretty serious." Hader supposedly inviting Bilson to his hometown to meet the parents during the holidays? Yep, that's a pretty major "next step" move, if you ask us.

Less than a week later, the alleged pair were spotted once again while grocery shopping at a Los Angeles-based Ralph's on New Year's Eve (via Page Six). Reportedly seen in their cart? "Two flavors of La Croix (mango and apricot), a case of Coca-Cola mini and firewood." Sounds like the actress and Saturday Night Live alum had a quiet night in planned to ring in 2020. Who doesn't like a little La Croix by the fire? 

However, all the rumors came to an abrupt end on Jan. 5, 2020, when this celeb couple confirmed their relationship in the most celebrity way possible...

Bill Hader and Rachel Bilson became red carpet official

After weeks of speculation that they were dating, Bill Hader and Rachel Bilson removed any doubt at the 2020 Golden Globes, where they became red carpet official. All smiles, they posed with their arms around each other and quickly became our favorite new celebrity couple of 2020.

Naturally, the Internet had some takes about pairing. "So... I didn't have Rachel Bilson dating Bill Hader on my 2020 bingo card???" one person tweeted, while another user wrote, "Rachel Bilson is really living out my dream dating Bill Hader and walking the red carpet with him. Good for her. Good for her." Meanwhile, another fan seemed to be taking the romance news very well, writing: "To be fair – whatever the winners, Bill Hader and Rachel Bilson have become official and THAT'S MY GOLDEN GLOBES HIGHLIGHT. I actually adore how cute they both are. I'm mad that I can't be mad. *reaches for the wine* Honestly, I'm fine."

They both left long-term relationships around the same time

This wasn't the first time either Bill Hader or Rachel Bilson have made headlines over a change in relationship status. In September 2017, Rachel Bilson and Hayden Christensen split after nearly a decade together. The former couple share a daughter, Briar Rose, who was born in October 2014. "She's full-time back in L.A. He's in Toronto," an insider told Us Weekly at the time. "They've been on the outs for a couple of months."

Two months later, Hader's rep confirmed to People that the SNL alum and his wife, filmmaker Maggie Carey, were divorcing after eleven years of marriage. The amicable exes share three young daughters and had called it quits months earlier in July. Back in 2013, Hader had joked with the publication about the key to a successful marriage, quipping: "Whatever your wife asks, say yes. Just say yes and your life will be so much easier. If your wife asks you to drive to LAX at 2 a.m. to pick up a piece of luggage, do it!"

Seems like Hader and Bilson brought a lot of experience to their blossoming relationship! 

Well, this is awkward

Long before getting together, Bill Hader and Rachel Bilson shared a sex scene in 2013's The To Do List, a comedy directed by ... Hader's then-wife, Maggie Carey. That might just deserve a big, old yikes. 

According to Newsday, the film stars Parks and Recreation alum Aubrey Plaza as "a high school valedictorian determined to shed her uptight image," with Hader playing her "slacker-dude boss" and Bilson portraying her "slutty sister." In a Q&A with the publication, the interviewer joked that it was "nice" of Hader's wife to write him a sex scene with Bilson. "Yes, well, you may've noticed, there was no kissing. We never kissed," Hader replied, adding, "To be totally honest, it made more sense for the scene." Later in the interview, Hader said he was "so proud" of Carey for getting the film made: "It got made by her sheer force of will. I was impressed and inspired by it." During another interview with USA Today (via E! News), Hader joked about his role in the film, saying, "It's like, 'No, you're not the hot guy in the movie. You get to have sex with Rachel Bilson but it's a mercy situation.'" 

While Hader and Bilson aren't exactly Brad Pitt and Angelina Jolie, we can't help but wonder whether Carey might just be regretting her casting choices.

Did Rachel Bilson have her eyes on a former Bachelor?

If you're wondering what a shock it was when Bill Hader and Rachel Bilson became a couple, the Hart of Dixie actress had only just shot down reports that she was dating former Bachelor star Nick Viall in the same month that the rumor mill latched onto her romance with Hader. 

Sitting down with Us Weekly in early December 2019, she set the record straight on her status with Viall: "We're just friends. We've always just been friends. He's a really nice guy." The dating speculation initially began after Bilson appeared on Viall's podcast that summer (more on that below), and only heated up once the pair exchanged seemingly flirty messages on social media. However, Bilson noted that they were "just messing around." 

After Bilson and Hader attended the 2020 Golden Globes, Viall seemed to take it all in stride, commenting on The Morning Toast's Instagram post about the couple's red carpet debut, "It makes it easier since I'm such a Barry fan." Well, that clears that up.

The single mom blues

In July 2019, Rachel Bilson appeared on Nick Viall's podcast, Viall Files, to discuss her dating life as a single mom. "I was talking to this guy ... a few months back. Anytime I would bring my daughter up, [he] would never pursue the question or ask more about her," Bilson explained to the former Bachelor star. "It was a red flag, 'cause anyone that you're going to get involved with if you have a kid, they have to be like all about the kid."

At the time, Bilson stated that her daughter hadn't "met anyone as of yet." The TV starlet continued, "It would have to be a very serious relationship ... If you're going to pursue something with someone, they have to be interested in the kid or be willing to be around the kid or babysit the kid — no, I'm just kidding."

Through our powers of deduction, we can only assume Bill Hader — who, of course, has kiddos of his own — was willing to be around Bilson's child. But did he want to babysit? That might just have been the true test of this celeb romance, friends.

Bill Hader once spoofed Rachel Bilson's show on SNL

Wait, we have time for one more Bill Hader and Rachel Bilson connection! During his time on Saturday Night Live, Hader appeared in "The Shooting AKA Dear Sister," a 2007 digital short by The Lonely Island, which spoofed the famously melodramatic second season finale of Bilson's former show, The O.C. — during which Mischa Barton's Marissa shoots boyfriend Ryan's older brother, Trey, all while accompanied by the song "Hide and Seek" by Imogen Heap.

As recapped by Entertainment Weekly, the parody "shows Bill Hader's character, Keith, get shot by his friend Dave (Andy Samberg), kicking off a chain reaction that sees Keith shoot Dave back, Dave shoot their mutual friend Eric (episode host Shia LaBeouf), all three men shoot Keith's sister (Kristen Wiig), and both police officers who arrive on the scene shoot each other. And with each resounding gunshot, the Imogen Heap song cues anew."

Very dark — and also completely hilarious — Us Weekly reports that the iconic clip had once again gained traction online when Hader and Bilson consciously coupled.