Glam Outlook
updates | March 15, 2026

17 Celebrity Couples That Make No Sense

Some celebrity couples go together like peanut butter and jelly while others are more like peanut butter and pickles. Check out the 17 weirdest celebrity couples ever.

Macaulay Culkin and Mila Kunis

1
The Hollywood Gossip

Before becoming Ashton Kutcher’s Baby Mama, Mila Kunis dated Macaulay Culkin…for EIGHT YEARS. Speaking of Ashton…

Ashton Kutcher and Demi Moore

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Ashton Kutcher and Demi Moore
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Ashton Kutcher and Demi Moore shocked the world when they went public with their relationship. They shocked us even further by discussing their very interesting and involved family dynamics with her ex Bruce Willis.

Tom Cruise and Katie Holmes

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Tom Cruise and Katie Holmes
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Everything about Tom Cruise and Katie Holmes’ marriage screamed publicity stunt until she divorced him, but hey, at least she got to wear heels.

Courtney Stodden and Doug Hutchison

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Courtney Stodden and Doug Hutchison
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In a very May-December romance, Courtney Stodden married Doug Hutchison, then 51, when she was only 16 years old.

Katy Perry and Russell Brand

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Katy Perry and Russell Brand
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We’re not quite sure what Katy Perry saw in Russell Brand that moved her to marry him, but their union lasted less than a year.

Chelsea Handler and 50 Cent

6
Chelsea Handler and 50 Cent
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Seems like Chelsea Handler knows her way around a lollipop. She dated 50 Cent for nearly a year.

Woody Allen and Soon Yi Previn

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Woody Allen and Soon Yi Previn
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Woody Allen and Soon Yi Previn have been together for over 20 years, but she was sort of his daughter so it’s super weird.

Jessica Simpson and John Mayer

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Jessica Simpson and John Mayer
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Jessica Simpson and John Mayer actually look great together, but she’s way not cerebral enough for him. He once said she was addictive, like “crack cocaine.”

Michael Jackson and Lisa Marie Presley

9
The Hollywood Gossip

Words cannot adequately describe how bizarre Michael Jackson and Lisa Marie Presley’s marriage felt to the world.

Kieran Culkin and Emma Stone

10
The Hollywood Gossip

Before Emma Stone moved on to Spider-man, she dated Kieran Culkin. Those Culkin boys know how to get the hotties!

Juliette Lewis and Brad Pitt

11
The Hollywood Gossip

Perhaps the strangest of Brad Pitt’s high-profile relationships was his 4-year run with Juliette Lewis.

Lady Gaga and Taylor Kinney

12
The Hollywood Gossip

The ultimate in WTF, Lady Gaga and Taylor Kinney seem like complete opposites, but if opposites really DO attract then maybe that explains this totally weird coupling.

Brody Jenner and Avril Lavigne

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Brody Jenner and Avril Lavigne
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A wannabe reality star and a wannabe rocker. Brody Jenner and Avril Lavigne were a match made in wannabe Heaven.

Olivier Sarkozy and Mary-Kate Olsen

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Olivier Sarkozy and Mary-Kate Olsen
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Now THIS is a weird May-December romance that kind of grosses us out. (At least Courtney Stodden has that whole “attention whore” thing going for her…) Mary-Kate Olsen is engaged to Olivier Sarkozy which just SCREAMS “Daddy Issues.”

Trace Cyrus and Brenda Song

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Trace Cyrus and Brenda Song
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Feather-tattoo faced Trace Cyrus was romantically linked to Disney channel sweetheart Brenda Song. And speaking of the Cyrus family…

Miley Cyrus and Liam Hemsworth

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Miley Cyrus and Liam Hemsworth
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We’re so glad Liam Hemsworth realized he could do way better (and way less crazy) than Miley Cyrus.

Alanis Morrisette and Ryan Reynolds

17
The Hollywood Gossip

The only thing Alanis Morrisette and Ryan Reynolds seem to have in common is that they’re both Canadian.