12 WEIRDEST CELEBRITY COUPLES OF ALL TIME

I like reading about news of celebrities dating other celebrities, especially if it’s a peculiar match. It’s my guilty pleasure. I myself am no stranger to peculiar pairings. I once dated a man who was a dog person. Imagine that! Me! A cat lady dating someone who preferred dogs! Oh, but that was so long ago. My next paramour was a lion-tamer. He liked big cats. You’d think it was a match made in heaven, but he judged my kitties heavily for being weak and tiny. He got “mauled accidentally” the following week. Serves him right.
There are so many mismatched couples in Hollywood that it makes me clutch my pearls! If you think about it, celebrities like dating other celebrities because they can understand their jobs, even if they’re not really a good match. This is why people in Hollywood get divorced too much. I have cats because they’re always there for me. Sure, we’re total mismatches at times, but at least we don’t have to deal with the paparazzi (yet.)
I put together this sweet list of the 12 weirdest celebrity couples of all time. Maybe you will be like me and be reminded of when you dated your polar opposite!

#12 – Jake Gyllenhaal & Taylor Swift

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Taylor Swift looks like a cutie pie. I don’t trust her at all. My momma always told me to be suspicious of girls like Taylor Swift. She’s young but she dresses like an old lady. Jake, on the other hand, reminds me of one of my nephews. He looks like a classic yet rugged American gentleman and Taylor used him to get on the music charts! From October 2010 to January 2011; these two were a hot item. I guess they were a little too hot though, since their love ended up catching on fire and left some burns. Jake appeared to take it in stride. However, Taylor seemed to take it more personally by translating her experiences with him into her 2012 studio release Red, featuring such hits like “We Are Never Ever Getting Back Together.” What went through Jake’s mind after hearing that song must have been something like, “Well, that was pretty swift.”

#11 – Kid Rock & Sheryl Crow

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You may know Sheryl Crow for being a country singer and Kid Rock for being, well, a “rapper” and the ex-spouse of Pamela Anderson that wasn’t Tommy Lee. Back in 2002, rumors started going around about Kid Rock and Sheryl Crow’s relationship.

Okay, they’re both “musicians”, but I don’t think Kid Rock deserves the title anymore. My cats hiss and scream bloody murder when they see a photo of Kid Rock on the Internet. On the surface, these musicians romance made some sense, considering both tend to love the USA and country/rock audiences. There is just something strange about seeing Sheryl Crow or Kid Rock coupled up with anyone for even a quick minute, considering the number of relationships they have had in the past. I guess both know how to share the love!

#10 – Mary-Kate Olsen & Olivier Sarkozy

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Okay, nobody better get mad at me and my kitties for saying this, but when I first saw a photo of these two, I thought they were father and daughter!

I remember the days when Mary-Kate Olsen played the part of Michelle Tanner with her sister Ashley on Full House. It’s unnerving to see her grown up now with a significantly older man. Olivier Sarkozy is a peculiar pick for even Mary-Kate. He is the half brother of former French President Nicolas Sarkozy, and he’s 17 years older!

Not that there is anything wrong with an age gap. I’d be lying if I didn’t say that I’d like to get back on the dating scene and meet a nice younger man. But for now, I suppose I’m happy to stay single enjoying the company of my cats. Now that they’re married, I have so many questions about their bedroom situation that should be left unasked

#9 – Josh Groban & January Jones

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Now isn’t this the cutest couple you’ve ever seen? These two look like an odd match. But, as I know from first hand experience, looks aren’t everything. I for one had a crush on Josh Groban for a little while because his music calms my kitties down, but eventually had to get over it because it was totally unrealistic.

Besides, I never even met the guy! For those unaware, Josh Groban is a professional singer best known for his cover of the song “You Raise Me Up” that fits in well at an opera house. January Jones is a different breed of artist as a model and actor performing on television as Betty Draper in Mad Men among other gigs. The couple had a good run for 3 years from 2003 to 2006. After breaking up, Groban told the media this was the longest he ever dated one person, which goes to show that even oddballs can make things work for a little while.

#8 – Mariah Carey & Nick Cannon

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Here is a couple I truly never would have expected. When I look at Mariah Carey and see her beautiful curves and equally beautiful voice, she always takes me back to Christmas time.

Every year, I play her album aptly titled Merry Christmas throughout the entire month of December. Nick Cannon, however—this man, I only know from MTV and that show about those rude “Yo momma!” jokes. They were together from 2008 to 2014 until Nick filed for divorce. It came as a bit of a surprise because they are one of the celebrity oddball couples that actually seemed happy when photographed together. It’s a weird and sometimes uncomfortable sort of happy, but happy nonetheless.
Additionally, the former couple have beautiful twins together, which made Nick’s divorce proceedings baffle me further. He seemed to be completely content with his life. Hmm, maybe Nick thought that things were getting too weird between him and Mariah?

#7 – Demi Moore & Ashton Kutcher

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Who in their middle age doesn’t remember when Ashton Kutcher and Demi Moore were together? All the media could talk about was their age gap of 16 years (with Ashton being 25 and Demi being 41!).

This did make their celebrity relationship a bit strange and made me jealous of Demi’s ability to snag a young and hot piece. The two met in 2003 at a casual dinner with friends (how painfully normal of them?!?), and despite their age gap appeared to genuinely enjoy each others company. One couldn’t help to get teary eyed when they divorced in 2013.

It’s still an impressive feat to stick out a marriage for close to 10 years (which is basically two lifetimes in Hollywood years.) Currently, Demi’s still on the prowl dating younger and hotter men—something that I’d really like to do one of these days. As for Ashton, he’s in a happy relationship with his Mila Kunis and just recently welcomed a daughter named Wyatt.

#6 – Chelsea Handler & 50 Cent

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If I had a beard right now, I would be stroking it with a puzzled look on my face. Fortunately, I just have the smallest amount of peach fuzz imaginable on a woman, that’s only noticeable when you look at it from the right angle in the sunlight.

The reason for this terrifying image is because I can’t begin to imagine rapper 50 Cent (a tough thug whose songs scare me and the kitties) together with Ms. Handler who is a moderately well known comedian and actress. After just a few months together, the two split. Mr. Jackson probably thinks to himself, “It’s better to stay out of the line of fire.” It feels better to be free than to be capped. I can’t say I blame them for going their separate ways if this relationship was at all like what goes on in 50’s mind.

#5 – Sandra Bullock & Jesse James

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When Sandra Bullock isn’t floating around in space, she reminds me a lot of myself. She’s independent and a self-starter. Sandra appears to be motivated to take on new and unique challenges.

For the longest time, I only knew her from the romance roles she played in films like The Lake House and Miss Congeniality. But she surprised me in 2014’s space drama Gravity. It’s almost like she isn’t from this planet. That last line isn’t too hard to believe since she dated and eventually married motorcycle builder and host of Monster Garage Jesse James.

This guy seemed like the exact opposite of Bullock, but I guess they got along for a while. Well, that was until March 2010 when a scandal came out with rumors that Jesse James had been cheating on her with several women. Bullock, being the independent woman she is, didn’t want to deal with these bullocks and filed for divorce not long after. Sandra, trust an old woman like me: Once a cheater, always a cheater—most of the time.

#4 – Sarah Jessica Parker & Robert Downey Jr.

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It’s hard to believe that back in the 80’s, Sarah Jessica Parker (Carrie from Sex and the City! All of my kitties have their counterparts from the show.) and Robert Downey Jr.

(also known as Iron Man) were together for several years. At the time, their pairing didn’t seem that unusual, since both had not yet gained the kind of fame and notoriety they have now. In a 2008 interview with Parade magazine, Robert Downey Jr. said: “I liked to drink, and I had a drug problem, and that didn’t jibe with Sarah Jessica, because it is the furthest thing from what she is. She tried to help me. She was so miffed when I didn’t get my act together.” Since then, Robert Downey Jr. has really changed his life, he quit the drugs, and was able to save himself. Sarah Jessica Parker went on to marry another 80s heartthrob, Matthew Broderick. At the end of the day, everything works itself out

#3 – Brooke Shields & Michael Jackson

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We will never know for sure whether Brooke Shields and the “King of Pop” ever truly dated. However, when Michael Jackson looks into your eyes, gives you a ring to mark your friendship (which was ongoing from age 13 until death), and says to you: “It sparkles and you sparkle,” you cannot help but wonder.

I loved them both when they were still little kiddies. Michael with his brothers, and Brooke with her caterpillar eyebrows! While recalling memories of Jackson, Brooke Shields noted that they never were intimate. I suppose this just means they never “got it on.” The reality seems to be a little different though, when we see a friendship as close as theirs apparently was. In 2009, she spoke at his memorial service. It was a sad day for the music world altogether.

#2 – Tyra Banks & Seal

The artist known as Seal has always made me laugh because I can’t help but picture myself going down to the Bahamas and checking out those marvelous creatures in the ocean. My personal thoughts aside, Seal and Tyra Banks (who was 11 years younger than Seal) dated briefly in 1996.

Their romance was short lived, and was only publicly noted at one event, the Essence Awards. The only misfortune that came from this couple dating for such a short period of time in the late 90’s is the simple fact that I was not able to see Tyra tell Seal: “You are America’s next top model!” God, what I would give for that.
As of 2015, Tyra’s still hosting “America’s Next Top Model” and as for Seal, he was married to another supermodel, Heidi Klum, and got divorced after almost 7 years of marriage.

#1 – Macaulay Culkin & Mila Kunis

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Easily the weirdest celebrity couple I have ever come across, Macaulay Culkin (little Kevin McCallister/Richie Rich who turned into a weird-looking hipster that my cats dislike) and Mila Kunis (the new Mrs.

Ashton Kutcher and the cutest thing to ever come from Russia!) do not appear at first glance to be the type of people to fall in love. But that’s apparently how it was for the span of their decade long relationship. To make this relationship even weirder: the two didn’t break up on bad terms. They continue to be great friends! At least they’re not like other Hollywood couples who have messy breakups and fight over the custody of children and/or cats. The only downside of their breakup was Macaulay’s downward spiral, which led him to turn to drugs to ease the pain—according to what he says.