The Strangest Things About Kate Beckinsale's Love Life

For the last couple of decades, Kate Beckinsale has had a solid but quiet run in Hollywood with credits in major films like Pearl Harbor, Serendipity, and Click (the latter arguably being one of Adam Sandler's most emotionally eviscerating films despite its 33% Rotten Tomatoes rating). For years, she served as the face of Underworld, a film franchise that spawned enough sequels to make us believe it's as immortal as Van Helsing, and most recently, she starred in the criminally underrated Amazon series The Widow. In short: Beckinsale has done a lot, but it's largely been overshadowed by her love life.

For someone whose relationships are always in the tabloids, Beckinsale has a shockingly laissez-faire attitude about dating. She's a stellar co-parent who forges tight bonds with her exes and their new lovers. She's the rare multi-millionaire who managed to divorce without it devolving into a battle of finances. She even has a track record of upgrading her 20-something boyfriends like she's trading in an old Lexus for a brand new Mercedes (if that Mercedes also happened to be a comedian). Basically, Kate Beckinsale is living the dream and proving that stardom after 40 doesn't have to be settled down. Life is what you make it.

Here's an eye-opening looking into the mother of one's unconventional dating life.

Kate Beckinsale is snuggly with her baby daddy

Kate Beckinsale is ultra-snuggly with her ex Michael Sheen. According to People, the actors initially started dating in 1995 after appearing together in a touring production of The Seagull. They dated for eight years — even having a daughter named Lily Mo Sheen in 1999 — but split shortly after the actress appeared in Underworld (it was a dramatic split, and we'll get to that later).

Somehow, despite all odds, Beckinsale and Sheen may still be each other's favorite people. They certainly don't miss out on the big moments. In 2018 alone, the Underworld actress spent her birthday and the Christmas holidays with her ex. It's not unusual to see the pair getting affectionate on Instagram. In 2016, she posted a photo of them in a warm embrace after their daughter got into college. Two years later, she was snuggling up to Sheen in a holiday Instagram post. She even once praised Sheen's then-girlfriend Sarah Silverman for setting a positive example in her daughter's life.

In an interview with Evening Standard, the actress opened up about their bizarrely affectionate relationship. It turns out that kind of love is simple as long as there's laughter involved. "It's so normal for us," she said. "We split up ages ago. We have been not together far longer than we were ever together. But I really love him and like him and we make each other roar with laughter."

Kate Beckinsale has been proposed to several times

For two people who adore each other so much, it's kind of puzzling that Kate Beckinsale and Michael Sheen never tied the knot. They dated for eight years and shared a daughter, so what was the hold-up? It seems like it was serendipity — or more realistically, Beckinsale's annoying habits.

In April 2020, the actress spoke to Vulture about her 2001 rom-com Serendipity. Yes, the nostalgia factor is very real. In the interview, the actress admitted that though she thought she'd "never be proposed to ever," she's been asked to tie the knot "several times." By who? She didn't say, but we do know the question never came from Sheen.

"I actually asked Michael outright, 'Why aren't we married yet?'" she told Glasgow's Daily Record in 2001. "I couldn't believe it when he said, 'Because every time I was going to ask you, you did something annoying.' So maybe if I can hold off being annoying for a while, then he'll finally ask me." From the looks of it, she wasn't able to reign it in.

Kate Beckinsale fell for a married man

Kate Beckinsale's relationship with Michael Sheen ended rather scandalously, but it didn't seem to get wrapped up in the same sort of bad press that plagued celebrities like Brad Pitt and Angelina Jolie or Kristen Stewart and Rupert Sanders. Still, what Beckinsale went through on the set of Underworld doesn't sound all that different.

According to Marie Claire, the actress met her husband-to-be Len Wiseman when she was filming the vampire drama in 2003, and they quickly fell in love. The only problem was that Wiseman was married, and Beckinsale was with Sheen. At the time, there were — as there always are — rumors of an affair, but the pair were adamant that no cheating ever occurred (a response seemingly straight out of the Angelina Jolie playbook). Not long after, they split from their partners and got hitched in a May 2004 ceremony in Bel-Air.

Weirdly enough, that minor scandal didn't seem to affect her relationship with Sheen very much at all. The pair remained tight, if only because they had to co-parent their kid. The actress told Entertainment Tonight that she's known the actor since she was 21 so he was "proper family" regardless of their history.

Kate Beckinsale doesn't need your spousal support

Kate Beckinsale doesn't need a man's money — especially if that man is her ex-husband. The actress was married to Les Wiseman for 11 years before they decided to separate. According to People, Wiseman filed for divorce from Beckinsale in October 2016, and both parties "waived their right to spousal support." Though it took four years to actually finalize the divorce, it was a shockingly low-key split.

An anonymous source that was supposedly close to Wiseman and Beckinsale told People that the pair still hung out after their separation when the British actress found herself in Los Angeles. "There has been no drama," the source claimed, "It's just not Kate's style."

Apparently, there genuinely wasn't any bad blood. The split was as simple as "complicated schedules" forcing the pair apart; however, Wiseman, who's the former husband of a school teacher, did try out the old Hollywood cliche of hanging out with models half his age in the midst of the separation. You only live once — or forever if you're Beckinsale's character in Underworld!

Things didn't end well with Matt Rife

In 2017, Kate Beckinsale jumped into the Gen Z dating pool when she shared some very public kisses with the then-21-year-old comedian Matt Rife outside of a West Hollywood restaurant. C'mon, girl. You know WeHo is for paps. Rife, who's best known for his appearances on MTV's Wild 'N Out, is about half Beckinsale's age, but it didn't seem to make much of a difference to the Underworld actress. A source told People that she was simply "enjoying her life" and "dating and having fun." It just didn't seem so fun when it ended, at least not according to the comedian.

In 2019, Rife doled out some advice to Beckinsale's new flame Pete Davidson, and he couldn't help but sound a little bit bitter about whatever happened when the couple called it quits. He told TMZ that their relationship was "complicated" with "a lot of ups and downs" and that the best advice he had for the Saturday Night Live comedian was to "run."

"Enjoy it while you can," Rife told TMZ. "I hope they're both happy. I hope it can build to where it's an established, good relationship. I don't know." Bitter much?

Kate Beckinsale was Jack Whitehall's rebound

Kate Beckinsale clearly has a thing for comedians, and right before she dated Saturday Night Live's Pete Davidson, she reportedly served as Jack Whitehall's rebound. According to People, Beckinsale was caught kissing the British comic at a karaoke bar less than a year after he ended his six-year relationship with Crazy Rich Asians star Gemma Chan — and she definitely tried to keep their fling under wraps.

According to a report in The Sun, the pair hung out at Hollywood hot spot Craig's, but left separately "to avoid being spotted." Whitehall then walked two blocks down the road where Beckinsale picked him up in an SUV. It's almost like when you're a teenager, and you ask your mom to drop you off two blocks away from the party, so no one sees. The pair do share a 15 year age gap, but that's never stopped Beckinsale in the past — plus she could probably teach the comedian a few things.

According to The Sun, Whitehall owned up to being bad in the sack despite his A-list lovers. "Sex with me is like arriving late at the theatre and trying to find your seat," he said. "Some shuffling, a bit of shushing, a pause and then from somewhere in the darkness just a whispered, 'Sorry.' And never an applause." In any event, it doesn't look like it ever got very serious between the two Brits.

Kate Beckinsale had a whirlwind fling with Pete Davidson

Kate Beckinsale's relationship with Pete Davidson was never one that made sense — but that doesn't mean it wasn't serendipity. The whirlwind couple was first linked by Page Six in January 2019 when they were caught flirting at a Golden Globes party. Soon after, they were reportedly planning a holiday together and kissing rink-side at a New York Rangers game. Unfortunately, the relationship didn't even last a full four months.

According to Entertainment Tonight, the pair split at the end of April. The downfall seemed to be the fact that they were clearly in two different phases of life, and not just because of their 20-year age gap. That year, Davidson moved in with his mother in Staten Island and was establishing his career in film. We've seen his basement apartment in Saturday Night Live sketches. At the time of this writing, Beckinsale is mom to a 21-year-old daughter of her own and has been an established working actress for nearly 30 years. 

"[It didn't work out because] it wasn't just the right time," Davidson admitted during an interview with Charlamagne Tha God. "I think I was going into another rehab ... I must have a pattern. I wasn't, like, right yet, and she had a lot of acting and work to do. She's like a superstar, so, it just didn't work."

Ariana Grande gave Kate Beckinsale her stamp of approval

Pete Davidson and Ariana Grande had a very high profile relationship, and it was the same sort of whirlwind that Kate Beckinsale found herself wrapped up in. It just didn't end in a broken engagement like it did with the "God Is a Woman" singer. Nonetheless, Grande seems like a uniquely supportive ex — a trait Beckinsale also shares — and gave the Underworld actress her glowing stamp of approval. According to TMZ, Grande claimed the new couple was "so cute."

Apparently, Beckinsale and Davidson really were so cute because she helped lighten the rather heavy few years for the SNL comic. Davidson has been honest about his mental illness struggle, including his borderline personality disorder diagnosis and stints in rehab. An alleged insider told E! News, "She has fun and doesn't take anything too seriously. She has spent some time with him and thinks he's very funny and charming. It's definitely not anything intense." 

At the time, Davidson probably needed a little levity in his life, but he did allegedly try to ramp up the intensity quickly, which seems to be a pattern that emerged in his relationship with Grande. According to HollywoodLife, Davidson was planning on proposing to Beckinsale just two months after they were spotted flirting at the Golden Globes party, but it doesn't look like anything came of it.

Publicity ruined Kate Beckinsale's relationship

Kate Beckinsale's relationship with Pete Davidson burned bright, but it burned out fast. Though Davidson said the timing was off, it may have actually been the comedian's fame that turned the actress off, which is an unusual move for a star of Beckinsale's caliber.

According to an insider who spoke to Page Six, Beckinsale "struggled with the attention on her relationship with Pete. He lives his life with his heart on his sleeve." It's true: Davidson regularly jokes about his relationships on Saturday Night Live and pretty much lives like an open book. That's actually what's made him so successful (well, that and dating Ariana Grande), but Beckinsale is a bit more private. Still, she didn't need to make out with him at a hockey game if she didn't want the tabloid's attention.

Of course, there are conflicting reports. An unnamed Hollywood executive told Page Six that the press was actually one of Davidson's main draws. "Kate loves the attention — both from a younger guy and the media," they said. "She hasn't been in the press this much in years." So, what's the truth? It seems like it's somewhere in the middle. The actress told the Los Angeles Times, "I'm surprised by the interest. I've never been in this position before — never dated anybody who comes with their own bag of mischief." Perhaps it was fun until it wasn't.

Kate Beckinsale is slamming Hollywood's double standards

In 2020, Kate Beckinsale dated her youngest boy toy yet. According to Page Six, the mother of one was first linked to then-22-year-old Canadian rocker Goody Grace at the start of the new year, when the pair was caught leaving a pre-Grammys party together. Apparently, she did not make Grace walk two blocks and wait to be picked up like Jack Whitehall. The musician is just one year older than Beckinsale's daughter — a notable power move in an industry where older men notoriously date younger women. The Pearl Harbor actress was taking none of the criticism that came with their sprawling age gap.

In her May 2020 Women's Health cover story, the 40-something actress slammed Hollywood's double standards. "It can feel like a little bit of a political act to be a woman over 32 who's having any fun at all," she admitted " ... And I witness men constantly doing whatever they like, whether that's in relationships, or deciding to buy a motorbike, or getting a tattoo." Beckinsale will not be held back. She's going to have fun how she pleases, 22-year-old boyfriend and all. Respect!

Kate Beckinsale moved in her Gen Z beau only to split

Kate Beckinsale's home is no stranger to Gen Z, and we're not just talking about her daughter (whose socks the Underworld actor apparently loves to sniff). At the onset of the coronavirus pandemic, Beckinsale added a second 20-something to her household: Goody Grace. Though she'd only been dating the musician for a few months, People reported in May 2020 that she had moved the rocker into her home for quarantine during COVID-19. "Kate enjoys his company," a source told the tabloid. "She finds him very mature, smart and creative. He entertains her with music, they cook and watch movies. She thinks he is the perfect quarantine boyfriend."

It's unclear if Lily Mo quarantined with the new couple or hung out with her dad Michael Sheen, but we're willing to bet that Beckinsale could school the two college-aged kids at beer pong. Either way, this live-in romance was short-lived.

According to E!, the pair split after just nine months of dating. Beckinsale reportedly deleted a comment she wrote on his Instagram, which signaled trouble. It was then reported that the actor unfollowed the musician, only to possibly follow him again. A source told Us Weekly that Beckinsale's friends didn't think her relationship was a "long-lasting/forever type of relationship." In other words: it was fun while it lasted, and at the time of this writing, it looks like Beckinsale is thriving all on her own.

Kate Beckinsale is a self-admitted 'worst wife'

With one divorce and a string of relationships with 20-somethings, Kate Beckinsale is the first person who's willing to admit that she's not the best wife — at least when it comes to the kitchen. The actress has, instead, focused her efforts on the bedroom. Apparently, you can't be skilled at both. If you try to be a jack-of-all-trades, you may just end up as a jack-of-no-trades.

In a 2008 interview with the British edition of Glamour (via Newshub), Beckinsale owned up to being a terrible cook. "I'm the worst wife in the cooking department," she said. "I always thought you can't be good at food and sex, but you can always order the food in. I would rather he didn't order in the sex!"

At the time, the star was still married to Les Wiseman, so perhaps she's since learned. We heard Jack Whitehall is a great cook, though he's self-admittedly awful in the bedroom. He even took part in a Father's Day edition of MasterChef that aired on BBC One. With their skills combined, we can only assume they'd be the ultimate power couple in a universe where she wasn't living with her 22-year-old lover. Better luck next time, dude.