Inside Bill Hader's Love Life (And The Big Compliment He Got From One Ex)

From his flamboyant club kid character Stefon on "SNL" to his turn as the angsty brother in "The Skeleton Twins" to his moody hitman persona on "Barry," is it weird that we kind of have a crush on Bill Hader? Perhaps not, since the actor has been linked to some of the most talented and beautiful actors in Hollywood.

While Hader was married for more than a decade, in recent years he's been enmeshed in several high-profile relationships, and we've followed along with interest. It turns out Hader is quite the catch, despite his unassuming demeanor and his dedication to keeping his private life (sorta) private. One ex nearly had a breakdown after their breakup, and mentioned that Hader had something very special she couldn't help but miss.

So let's dig in because this article has everything: vaguely overlapping relationship timelines, sex scenes, hiking, and that thing where you break up with someone and it's more painful than childbirth.

Before Bill Hader became something of an unlikely heartthrob, he was a family man married to director and screenwriter Maggie Carey. The two met through a mutual friend and Hader was smitten for real once he first set foot in Carey's apartment. "She had Star Wars curtains. I walked in there and in my head, I thought: This is awesome and we will be married," he told The Washington Post. His prediction was right, and the two were married in 2006.

In addition to sharing three daughters together, the couple had their work in common. While Hader had a long run as a cast member on "SNL," Carey directed films like "The To Do List," and episodes of series such as Netflix's "Love," and HBO's "Silicon Valley." It sounds like the two had a healthy outlook on the business, even when it came to Hader doing sex scenes. In an interview with Elle in 2015, Hader said, "... in 'Trainwreck,' I make out with Amy [Schumer] a lot. Maggie's like, 'That's cool. Our deal is, If you shoot a sex scene you have to come home and have sex with me.' Amy and I made out so much, I got Maggie pregnant during rehearsals. We hadn't even shot the movie yet." The couple also spoke about working together on "The To Do List" in which Hader starred. "If it was me directing the movie, I wouldn't have cared as much but because it was my wife, I was very protective," Hader told USA Today.

While Bill Hader and Maggie Carey seemed like the perfect low-key Hollywood couple, the marriage ultimately did not last. The two split in 2017, with court documents filed by Hader citing irreconcilable differences as the cause. And while neither has spoken publicly about the break-up, Hader alluded to his stressful time on "SNL" as a possible contributing factor. "When I was on 'SNL,' I was a bit of a basket case," he told Variety. "It could not have been easy on my wife at the time. I was so consumed with work and anxiety."

But it appears as though time has healed wounds, and the former couple has an amicable relationship. In 2018, Carey even directed an episode of the HBO hit series "Barry" in which Hader stars as the titular character. And Hader has been straightforward about the status of he and Carey's relationship. "I'm friends with my ex-wife," he told Variety in 2019. We love to see exes making it work!

In 2019, it appeared as though Bill Hader had begun dating fellow actor and "The O.C." star Rachel Bilson. The two were spotted by TMZ at a Starbucks in Tulsa, Oklahoma, near Hader's hometown. The pair had some of Hader's family members in tow, which of course led to speculation that the relationship was, in fact, serious.

Hader and Bilson starred together in "The To Do List," which had to have stung a bit for the film's director, Hader's ex Maggie Carey. The couple looked happy (and stunning) together when they became red carpet official at the 2020 Golden Globe awards.

Hader and Bilson even had the blessing of Hader's "Barry" co-star Henry Winkler. The legendary actor told a red carpet reporter that the relationship worked "because Bill is great and Rachel is so lovely" (via US Weekly). Bilson's buddy "Bachelor" alum Nick Viall also shared his thoughts on seeing the couple together at the Golden Globes "I think it's great. ... They seem like a cute couple," he told US Weekly. They really did seem like a great match, but alas, the relationship did not stand the test of time.

Bill Hader and Rachel Bilson broke up not long after making their first public appearance as a couple, which happened to coincide with Covid-19 lockdowns. The isolation of the pandemic made the split extra difficult for Bilson to endure. "I could not leave my house ... I had nothing else to do but sit in it, and deal with it and feel it," Bilson said during an episode of her "Broad Ideas" podcast with guest Aubrey Plaza (via Us Weekly). "It was probably the hardest thing I've ever done⁠, harder than childbirth," Bilson said, adding that it "hurt like a motherf**er." Girl, we hear you.

Ultimately Bilson thought the experience made her stronger, saying "If you actually face it, you can come out of it and be like, 'OK, I did that and I'm ready for the next thing.'" And, of course, the actor has carried on and in 2022, Bilson began dating actor Zac LaRoc, And yet, there was something specific she missed about Hader, which she revealed to "Broad Ideas" guest Tommy Dorfman (via Vanity Fair). "His big d**k," she said, laughing. Well, no wonder that breakup was so tough!

Bill Hader's next relationship was with another beloved actor, this time "Pitch Perfect" star Anna Kendrick. The two met when they starred as siblings in the 2019 holiday film "Noelle." It would be several years, however, before the pair began dating and their relationship was confirmed by US Weekly in 2022. Sources said that Hader and Kendrick bonded over their shared sense of humor and enjoyed doing normal couple things like hiking and chilling with friends as opposed to being seen out and about partying it up. A source also claimed that Kendrick had grown close with Hader's three daughters, a sure sign that this relationship was built to last.

Despite our shipping these two, Hader and Kendrick called it quits in June of 2022. Neither spoke publicly about the breakup, but Hader told The Hollywood Reporter in March of that year that he was keeping mum about his personal life for the sake of his kids. "They just want me to be their dad," the actor said. "They just want me to sit and watch 'Encanto' over and over and over again. So that's what I do."

In the fall of 2022, it appeared as though Bill Hader was back on the dating scene, having been spotted out with stand-up comic and "Beef" star Ali Wong. According to Page Six, the two dated briefly following Hader's split from Anna Kendrick and Wong's divorce from entrepreneur Justin Hakuta, but called it off after just a few months. A source told Page Six, "They're just super busy with things, but [the split] was certainly amicable. They're certainly friends."

Well, they must have stayed friends and that friendship must have blossomed, because Hader and Wong were back together as of April 2023. Hader first dropped the hint that he was seeing someone in an April 2023 interview with Collider. "My girlfriend and I were just figuring out that I haven't had a vacation in 10 years," the actor said, adding, "I went with her to San Francisco, but that doesn't really count."

Hader and Wong were seen together soon after, hanging out in casual outfits, sharing kisses on Wong's 41^st birthday. It appeared they'd gone on a hike, then later celebrated with a dinner together. Since Hader is referring to Wong as his girlfriend, we're going to assume it's serious this time!