This Is What It's Really Like to Date a Celebrity, According to Some Very Lucky People

Wondering how to date a celebrity? These people revealed the famous people they dated on reddit.

Anna Quintana - Author

Oct. 17 2018, Updated 12:18 p.m. ET

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Everyone has fantasized about dating a celebrity. For me, it was Justin Timberlake (who could resist those NSYNC-era curls?) and two decades later, it would be hard to deny that if the "SexyBack" singer came up to me on the street and asked me out on a date, I would turn him down. Sorry, Jessica Biel, but it's the truth. 

Though dating Justin, or any famous person for that matter, has yet to happen for me, there are some lucky people out there who know what it's like to date a celebrity. Thanks to reddit, they came together to share their experiences — and TBH, dating a Hollywood star is not as glamorous as it seems. 

Dare we say, they're just like us when it comes to finding love? From Elvis Presley to Miley Cyrus, keep scrolling for dating stories involving your favorite celebs and the girl (or boy) next door. 

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1. Ben Affleck and Matt Damon

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"A friend of mine's Mom was a student at Boston College in the late '80s or early '90s. She and her friend went on a double date with two guys their age. The whole date, they talked about a script they had written and how it was going to be their ticket to the big time. Afterwards, her and her friend decided that the two guys were pretentious and kind of annoying.
Those two guys were Ben Affleck and Matt Damon. The script? Good Will Hunting."


2. 'Game of Thrones' stars

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"Was seeing Hannah Murray (Gilly, GOT or Cassie, Skins) for awhile around 10 years or so ago. Just when season two of skins came out. Turns out a girl I worked with knew her, I fancied her, and so we orchestrated a meeting between us.  She organized a coffee with her, and I just so happened to stumble into the cafe. We hit it off and we ended up having a little thing for 5 months or so. We went to the cinema, ate and drank. She is highly intelligent, very perceptive and really quite funny. I was young and rubbish at dating, and am guessing she wasn’t too experienced either. In the end she called me one day after a week of silence and dumped me because she was going to Uni. Fair enough. I’m super happy for her and think she’s a great actress."


"I went on two dates with Emilia Clarke about 5-6 years ago. Really witty! And really sweet. Things didn’t work out between us (obviously) but god I wish they did."


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3. Kristen Bell

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"I dated Kristen Bell in high school. Her mom still tells me she wanted to marry me back then. She was super funny and basically looked the same as she does now... she doesn’t seem to age. She broke up with me on New Year's Eve then hooked up with some dude that night, allegedly. No hard feelings, we were friends after and I’m super happy for her success."


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4. Comedians

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"My cousin dated Will Ferrell way back when he was just starting on SNL. I think it was mainly sex. She said he was super sweet, but very quiet and awkward. And more subtly funny in person than on tv. She was the one who ended things and we never let her live it down. She's become very successful in her own right though." 


"Adam Sandler went to the same middle school and high school as me (at a different time) in NH. He dated my 8th grade teachers daughter for a while before he moved to NY for SNL. He was well liked, and he even called my 8th grade teacher to wish her well on her retirement, some 20 years later."


"I went on one date with Hannibal Burress. He was in my city briefly after doing a benefit gig elsewhere a few years ago and we matched on Tinder, met up for a drink before his flight left later that evening. He’s a cool dude, I had fun. Did not have sex, sorry to disappoint. Apparently he’s pretty notorious for being on Tinder so I feel like a lot of people probably have a similar story lol. Pretty D-list, but my fiancé went to HS with one of the girls on VH1’s Black Ink Crew, I guess they hooked up a few times."


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5. Chris Pratt

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"My cousin dated Chris Pratt right after high school! She said they never slept together though because he was too sweaty. She didn't say it but I think she's the reason he went to Hawaii."


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6. Hayden Panettiere

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"My brother briefly dated/hung around Hayden Panettiere right after her first Disney movie came out (Tiger Cruise, it was one of my favorites at the time!), before Heroes or anything. Apparently she had family who had a lake house in our hometown and they met at a party and started to hang out when she would visit her family. She even came to the strawberry festival with me and my brother (mind you, I'm ten years younger so I was like seven or eight at the time) and was really nice to me because I was so awestruck to be meeting a Disney actress. She even made a DIY candle with me at a festival booth that I kept for years afterward. Nicest girl he ever introduced me to, second only to his later fiancée."


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7. Her name is Kate Beckinsale.

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"An English teacher of mine went on one date with the actress of the Underworld movie series. He said that she was a mousey shy girl who was very nice but they didn't click at all. We tested him that he could have been a kept man in the Mediterranean somewhere but ow he was teaching us s--theads." 


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8. Music Legends

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"My late great aunt went on a blind date with Frank Sinatra. Apparently it went well and he asked for a second. She declined — didn’t like his music."


"My grandmother dated Elvis before got famous. She wasn't allowed to see him after he went to a family bbq, because my great grandparents thought he would be trouble. I guess after watching a bio-pic about his life, they were right."


"My friend's grandma dated Jimi Hendrix, apparently she was one of the last to do so, before he sadly passed. Don’t know much more about it. I did, however, see a picture of the two of them together — very nice."


"My former boss went on one date with Freddie Mercury when they were both 17. She said he was very nice, but they didn't have much in common. She said she would never have guessed that he was also interested in men."


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9. Destiny Cyrus aka Miley Cyrus

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"One of my best friends dated Miley Cyrus (then Destiny Cyrus) back in Middle School. We all went to the same elementary school then started middle school together. Mind you this is all before Hannah Montana was created. Back then her and her brother (Trace Cyrus, of Metro Station Fame) were just Billy Ray Cyrus's kids which didn't mean much too us back then. They dated for all of our 6th grade year until she moved to Toronto I believe to start pre-production on a Disney show, which we would later find out to be Hannah Montana.
He wasn't too beat up about it as he described her as being kinda crazy. One story I remember is that after a mutual friend of theirs was broken up with by her boyfriend, Miley tried to get my friend to make out with her to cheer her up, which he refused to do.
Also, after the show came out and her face was all over Tiger Beat and 17 magazine, we would rip out the pictures of her, cut a hole in the mouth, hold them up to our face and chase him around saying, "I miss you *****, come to hollywood and be with me!"
We probably could've been a little nicer about it."


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10. Tiera Skovbye

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Source: Instagram
"I dated a woman who is currently a regular on CW's Riverdale. We dated some years ago when she was younger. She was a fairly successful model and actor at the time, even more so now clearly. We met while working on the same television show and I asked her out. Didn't expect her to say yes as she was way out of my league. But she did and we hung out for a month or so. She eventually went back home and we tried long distance for a few weeks before deciding that it wouldn't work. We've talked once or twice over the years but she is firmly in a different social strata now. Overall, she was very nice and fairly intelligent but very focused on being an actor/model and didn't really know any other lifestyle.
EDIT: I know everyone is probably annoyed that I don't say the name of the person in question but I dunno it feels kinda wrong.
EDIT2: Fine. It was Tiera Skovbye. Might as well add a bit more detail."


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11. Monica Lewinsky

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"No one ever believes me but I very briefly dated Monica Lewinsky. I was much more into her than she me so, much like Bill Clinton, I did not have sexual relations with that woman. I thought she was amazingly intelligent and I think people who slag her off really are being hypocritical and sexist." 


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12. Doctor Who

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"My friends mum dated David Tennant for a year when she was 19 apparently. I’m not sure how true it is because she doesn’t talk about it much when questioned and honestly I would never shut up about it if it was me, but she said he was very funny and sweet. I think the breakup was mutual. Not much of a story really."


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13. So many regrets.

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"My English teacher went to high school with Bill Nye. He asked her to the prom and she turned him down because 'he was a nerd.'"


"My aunt rejected Snoop Dogg during their teens, they went to the same high school. Apparently he was a stoner at the time, crazy right? Nate Dawg and Cameron Diaz went to the same school as well."


"My Mum turned down Brad Pitt in a bar in Ireland. He had just landed his role in Thelma & Louise so was only really known for his Levi ad but my Mum didn’t know who he was. He asked to buy her a drink and she declined. He told her about being the Levi model and she awkwardly declined again. She really regrets it now. (Oh and she turned him down because he had really bad acne which she feels bad about now but she was 19 at the time)." 


"My aunt rejected Jim Carrey when they were younger."


"My friend turned down Jennifer Connelly. In the mid '80s she spent the summers in a small town on E. Long Island. This was after she was in The Labyrinth but before The Rocketeer. Parents were friends somehow so she would hangout with a local circle of friends. One evening she asked him to go on a walk... he said no. He is still made fun of it to this day. She was very nice by all accounts."


So, it looks like your best chance of dating a celebrity is dating them before they get famous. 

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