'Skeletal' Angelina Jolie Wearing Kids' Clothes After 'Scary' Weight Loss? News 'Skeletal' Angelina Jolie Wearing Kids' Clothes After 'Scary' Weight Loss?
Jennifer Aniston, Brad Pitt In Love Again? Celebrities Jennifer Aniston, Brad Pitt In Love Again?
What Is Taylor Swift’s Height? How Tall The Pop Star Really Is Celebrities What Is Taylor Swift’s Height? How Tall The Pop Star Really Is
Prince Harry Had A 'Secret Mental Breakdown'? Royals Prince Harry Had A 'Secret Mental Breakdown'?

Kate Beckinsale is one of the hottest women in Hollywood, so it may come as a surprise that she lives such a straight lifestyle. The actress claims she's never had a drink or done drugs, nor has she ever had a one night stand. If she has one guilty pleasure, it's the company of younger men.

From 1995 to 2003, Beckinsale, 47, dated age-appropriate actor Michael Sheen. (The couple shares a 21-year-old daughter, actress Lily Sheen.) She married Underworld director Len Wiseman the following year, but her then-husband filed for divorce in 2016, citing irreconcilable differences.

Since then, Beckinsale has been playing the field with men who are nearly half her age. And she hasn't been shy about it, either. Tabloids have had a field day documenting her date nights around LA (and the PDA that ensues). In an industry where it's common to see younger starlets on the arms of older men, we're all for Beckinsale turning the formula on its head. Here's a look at the boy toys she's had over the past few years.

Matt Rife

Matt Rife wearing jean jacket and black bandana
(Kathy Hutchins / Shutterstock.com)

Shortly after her husband filed for divorce, Beckinsale began dating comedian Matt Rife. The two were first spotted in June 2017, when they were making out in front of a West Hollywood restaurant. Rife, who is best known for his spots on Nick Cannon's Wild 'N Out, was 21 at the time; Beckinsale was 43. According to PEOPLE, the age difference wasn't a factor for the actress because she considered her beau "an old soul." But their split one year later was acrimonious. When TMZ caught Rife in front of an LA comedy club in 2019, he had one word of advice for her future boyfriend Pete Davidson: Run. “I don’t really have any solid advice," Rife added. "Just be careful.”

Jack Whitehall

Jack Whitehall wearing tuxedo at the 2020 Brit Awards
(Cubankite / Shutterstock.com)

Beckinsale apparently has a thing for funny men. In November 2018, she had moved on to another comedian: 30-year-old Jack Whitehall. The two were seen having dinner at West Hollywood hotspot Craig's before hitting up a nearby karaoke bar. Despite being 15 years her junior, Whitehall wasn't afraid to make the first move. Witnesses caught him pulling the Serendipity star in for a kiss, which quickly escalated to a full-blown makeup sesh. At 3 am, they took things from a bar booth to a room at the London Hotel. Neither has ever commented on the date. In fact, Whitehall referred to himself as single in a stand-up routine shortly after their tryst.

Pete Davidson

Pete Davidson wearing sunglasses and black suit jacket at The Dirt premiere
(DFree / Shutterstock.com)

In January 2019, Beckinsale made waves when she was seen flirting with Saturday Night Live star Pete Davidson at a Golden Globes after-party. Davidson, who was 25 (or 20 years her junior) at the time, was fresh off his split from Ariana Grande. What transpired was a whirlwind romance that echoed his last relationship. Within a matter of months, Davidson and the Pearl Harbor actress were attached at the hip, making out at sporting events and film premieres with reckless abandon. By March, he was seen having dinner with Beckinsale's mom and step-dad at Nobu, which hinted that their pairing was more than just a fling.

Beckinsale confirmed the serious nature of the relationship. "I think if you liked the person less, you would bow out of it, she told the LA Times. "If that were the main thrust of the relationship, there would be a problem. But it’s not." Alas, it was over in all of four months. "They’re still friendly but are not on romantic terms," a source told ET.

Goody Grace

Perhaps Beckinsale was ready to try something new. In January 2020, she took a break from dating comedians and hooked up with 22-year-old singer-songwriter Goody Grace. The two made their involvement with one another public in April with some innocent hand-holding; two months later, Beckinsale declared "I love you" on the artist's Instagram account. But by October, sources confirmed to Us that the two split up after nine months.

Why Kate Started Dating Younger Men

Beckinsale has been anything but shy about her preference for younger guys. In a May issue of Women's Health UK, the actress addresses the double standard she's subject to because of her choices. "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 said.

" ...Being goofy, and going out, and not going, 'Oh my god, I’m going to sit home and anticipate menopause while crocheting.' Unless you’re doing that, it somehow seems to be risqué, which is just ridiculous to me," she added.

Beckinsale is also famous for her social media clapbacks at haters. For instance, when an Instagram user asked, “Why do you keep dating guys that could be your children?” she replied, "Every relationship I have had has been solely to annoy you." When another user expressed disappointment in her dating choices, she remarked, "Fairly let down by your wonky beard but thought possibly rude to say."

We say more power to her, and we look forward to seeing who the next man in her life is—no matter how young or old he is.


Everyone 4 Non Blondes' Linda Perry Has Written Songs For