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Celebrity Dates That Were Weird, Awesome or Super Expensive

Everyone knows that dating can be very, very weird. But did you know that that’s true no matter who you are or what your bank account balance is? We’ve taken a look back and found out that celebrity dates can be just as amazing (or amazingly bad) as anyone’s — although we admit celebs often have a little bit more to spend.

Let’s look at some of the most amazing, most shocking and most expensive celebrity dates of the past, from some of Hollywood’s most successful couples to some famous relationships gone bad.

More: Celebrities and Online Dating: Who Does It, Who Wants To

Charlize Theron puts on her midnight hiking boots

Just last month, actress Charlize Theron dished to Howard Stern that she had gone on a wonderful date. A year after her split with Sean Penn, the Atomic Blonde star said she went on a 9-mile hike in the middle of the night with an unnamed beau, the full moon above them. While a long, dark trek might sound more like a nightmare than a good time, Theron said it was incredible, private and fun. She wouldn’t say who the man was or if he was famous, but she did say he was a “cool dude.”

More: The Different Looks of Charlize Theron Through the Years

Kanye West’s lavish engagement date with Kim Kardashian

Kanye West and Kim Kardasian's Engagement
Image: WENN

Perhaps the most important date of a relationship is the proposal date. Kanye West pulled out all the stops for Kim Kardashian when he asked her to be his wife in 2013. The righteous rapper rented out the San Francisco Giants’ baseball stadium, hired a 50-piece orchestra, and hid the couple’s friends and family in the dugouts before popping the question. Then he pulled out a 15-carat diamond ring in front of a Jumbotron that said, “PLEEEASE MARRY MEEE!!!” How can you say no to all that planning?

Justin Bieber made a Titanic gesture to Selena Gomez

Speaking of renting out stadiums, let’s not forget the time when Justin Bieber rented out L.A.’s Staples Center so that he and Selena Gomez could watch Titanic in private. And this was after the couple spent the day at the beach and caught Demi Lovato in concert across town. The Biebs and Gomez are no longer together, but this blockbuster date will go on… and on… in our memories.

Bear Grylls climbs a mountain for nothing

This might have been Bear Grylls’ most taxing adventure: He told The Huffington Post about his worst date ever, in which he prepared a three-course picnic on top of a mountain. Of course, his date didn’t even show, let alone climb the mountain with him, and the picnic was rained on. “It took me a full day to carry it all up there,” the survivalist said.

Channing and Jenna Dewan Tatum escape to the wilderness

For their anniversary, adorable couple Channing and Jenna Dewan Tatum went to a cabin in the wilds of Michigan for a lake vacation away from all of the worries of the world, including the internet. While they had a wonderful time living the rustic life with their 4-year-old daughter, Everly, they also quickly got a bit tired of their slightly scary surroundings. At one point, both Channing and Jenna said they were going for walks — and then bumped into each other at the internet café.

Britney Spears and Justin Timberlake go full denim

We cannot possibly talk about amazing celebrity dates without taking the wayback machine to 2001, when Britney Spears and Justin Timberlake went on their unforgettable Denim Date. The power couple of the early-aughts stepped onto the red carpet at the American Music Awards in what might be the most memorable matching date attire in all of history. Sadly, their romance wore out like your favorite pair of blue jeans.

Tom Hiddleston wears an “I [heart] T.S.” shirt on a date with Swift
How can we forget July 4, 2016, not only our nation’s birthday but also the day that actor Tom Hiddleston went on a beach date with Taylor Swift while wearing a shirt that said “I [heart] T.S.”? The romance only lasted three months, and Hiddleston claims he borrowed the shirt from one of Swift’s friends as a joke. Still, we “heart” the weirdness about this event happening.

Russell Brand breaks out black diamonds for Katy Perry on their first date

The marriage between Russell Brand and Katy Perry was doomed to last little over a year. But their first date was totally romantic. After a quiet dinner, Brand gave Perry a Hindu hand of peace made out of black diamonds. The pop singer also asked the comedic actor for a copy of his autobiography, which was in the car. Brand signed it, “You’re a mermaid and I’m drowning,” then put the necklace on Perry. Sadly, this mermaid-human relationship did not work out.

Ashton Kutcher takes Demi Moore to In-N-Out

ashton kutcher and demi moore
Image: WENN

Ashton Kutcher and Demi Moore had a 10-year relationship. Though it ended in divorce in 2013, it wasn’t a bad run, as far as Hollywood relationships go. The couple began courting at an odd place: In-N-Out Burger, where Kutcher swears the best burger in town was served at the time. The cheap date tactic must have been a success because the couple went on to have years of happiness together.

More: Ashton Kutcher & Mila Kunis Have a Trilingual Daughter

Kim Kardashian gets Chipotle with Reggie Bush

Fast food does not always make for great first dates, though. When asked about her worst date ever, Kardashian was quick to bring up her first date with the NFL star, in which she had to pick him up from the car wash before a less-than-romantic meal at a local Chipotle. Still, the couple dated for two years.

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