Tom Cruise and Cher
The 80s were a crazy time, and nothing could be more insane than this bizarre couple! The legendary singer was nearly double the age of the "Risky Business" star at the time, but she has described their relationship as really incredible. She even gushed that Cruise was one of her top 5 lovers of all time. If you could turn back time, Cher...
Ariana Grande & Big Sean
This recent development definitely had us saying "what!?" mostly because Ari still looks like she's in grade school. They've been spotted together a lot, and Ariana has spoken about moving towards a relationship, but she likes to play coy and keep the details of her life mostly hidden.
Hayden Panettiere & Wladimir Klitschko
Not many people would have guessed Hayden would end up with a giant Ukrainian fighter, so much so that she's planning on marrying him and is actually a few months pregnant already!
Lady Gaga & Taylor Kinney
Lady Gaga is just so eccentric, we would never have expected her to end up with a seemingly-normal actor and surfer dude like Taylor Kinney. They met in the filming of "You and I" and have been dating since.
Mary Kate Olsen & Olivier Sarkozy
Wow, who would have thought Mary Kate Olsen would end up with the brother of a president of France!?!? She must like the high profile life. This dude's face in bottom center really says it all though, "What the heck is going on here?? And wow being single sucks."
Brody Jenner & Avril Lavigne
Although they both love trucker hats, there seems to be nothing that these two have in common. Avril is known for being punky and going against the grain, while Jenner, who starred in "Laguna Beach" and is stepbrother to the Kardashian sisters, is as "with the grain" as it gets. The pair dated from 2010-2012 and then went their separate ways.
Sandra Bullock & Jesse James
What is this America's sweetheart doing with this tattooed motorhead with a history of dating strippers and porn stars!? Everyone was shocked when Bullock married bad boy Jesse James in 2005, but not so much when it was revealed that he had an affair with a fame-seeking model. The couple broke up in 2010.
Christina Hendricks & Geoffrey Arend
Hendricks is one of the most beautiful women in Hollywood and is well-known for her role on "Mad Men," while Arend has a more unconventional look and may only be recognizable for a few supporting roles in "Garden State" and "(500) Days of Summer." Regardless of these differences, the two have been madly in love since 2007.
Edward Norton and Courtney Love
We understand Love and Kurt Cobain but doesn't her dalliance with Edward Norton just seem weird? The two were together for 3 years in the late 90s, and even got engaged. They met after costarring in "The People vs. Larry Flynt."
Chelsea Handler and 50 Cent
Yes, 50 Cent did indeed woo the blonde comedian. It's common knowledge only because the gabby talk show host hasn't stopped talking about it since. The stand-up force still uses her relationship with the rapper as comic fodder in her act.
Ashley Olsen and Lance Armstrong
In 2007, the 21-year-old "Full House" star was spotted making out with the famous cyclist 15 years older than her. Armstrong has been linked to a ton of A-listers, and Olsen has as well, but this pairing is definitely the weirdest.
Mila Kunis and Macaulay Culkin
From 2002 to 2010, that scared little boy from "Home Alone" and Jackie Burkhart were an item! The long-term pair split in 2010, with Kunis stating she needed to be with someone she could see herself marrying and having children with. She didn't have to search for long, as she began dating her "That 70s Show" co-star Ashton Kutcher 2 years later and is now engaged and expecting with him.
Ashton Kutcher and Demi Moore
Before he settled down with Kunis, Ashton was in a very high-profile relationship with Demi Moore. The two met in 2003 — he was 25 and she was 41, but that didn't deter them, and Demi became the face of the newly-rising term "cougar." They married 2 years later, and stayed together until their divorce in 2011.
Alanis Morissette and Ryan Reynolds
That's right, the grungy "You Oughta Know" singer and the perky funnyman dated from 2002 to 2007, in what seems to be one of the most mismatched pairing in Hollywood. Maybe it was national pride that brought the two together, as they are both proud Canadians? Alanis has had a past with funny guys, as she famously dated "Full House" star David Coulier, but Reynolds seems to prefer blondes, going on to date Scarlett Johansson and marry Blake Lively.
Mariah Carey and Nick Cannon
What? The Diva and Nickelodeon star somehow found each other and have made a life together that proves there is such a thing as soul mates. Despite an 11-year age gap, the two unlikely lovers have been happily married for years.
Amber Tamblyn and David Cross
This is one of the weirdest couples out there, but they're also one of the most in love! David Cross, who famously played Tobias Funke in "Arrested Development," is nearly 20 years older than "Sisterhood of the Traveling Pants" star Amber Tamblyn, but that didn't stop them from tying the knot in 2012. The married couple is best buds with Tamblyn's "Pants" co-star Blake Lively and her hubby Ryan Reynolds.
Rihanna and Shia LaBeouf
Could any couple be more mismatched than the sexy and cool Rihanna being with the goofy "Even Stevens" star!? The two actually only went on 1 date back in 2007, and the spark wasn't there. Yeah, we bet it wasn't — we can't imagine the two really hitting it off.
Seal and Heidi Klum
Klum could have any man she wants, so the public was left to wonder why she chose a semi-famous singer 10 years older than her. Not only did this mismatched supermodel and pop singer get married, they also produced three beautiful children. Despite recent rumors that the storybook couple may be getting back together, they deny a reconciliation.
Simon Cowell and Carmen Electra
Simon Cowell is no stranger to younger and more attractive women, and Electra is no stranger to older men, so the pair kinda makes sense we guess, but it's still weird! The two met when Electra was judging on "Britain's Got Talent," and began dating even though Cowell was married at the time. They were still together when it was announced that Cowell impregnated another woman. It's a no from us, Simon.
Dennis Rodman and Carmen Electra
Yep, she got around. The stunning Electra liked her men eccentric and they don't get more eccentric than basketball's bad boy. She married Rodman in a Vegas chapel in 1998, and the tabloids had a field day, before the couple split less than a year later.
Jennifer Aniston and Adam Duritz
Somehow, the Counting Crows frontman Adam Duritz made his way through the gorgeous "Friends" cast by dating both Jennifer Aniston and then Courteney Cox. We guess they both have a thing for dreadlocks? Although maybe not too much of a thing, as Duritz admitted that he and Aniston never slept together during their relationship.
Megan Fox and David Gallagher
Remember Simon from "7th Heaven?" He dated Megan Fox! From 2003-2004, the young Hollywood hopefuls were figuring out the world of celeb stardom together. Obviously, Fox was able to figure it out but Gallagher was not.