It’s practically the stuff of teenage dreams: your high school sweetheart goes on to become a superstar. Or maybe you have a run-in with someone who’s already on their way to becoming famous and, somehow, they pick you.
It’s something some folks over on Reddit wondered about, asking others what it was like to date someone famous—or someone who would eventually become famous. What was it like? How did it end? And are they still in touch? The answers range from sweet to messy to downright unbelievable, and while “dating” might be used a little loosely in some of them, they’re pretty entertaining—whether you’ve always dreamed of joining your celeb crush on the red carpet or can’t imagine anything worse than that kind of spotlight.
#1
I dated Chester Bennington (lead singer of Linkin Park) for about 10 months just whilst they were starting to become big/tour regionally. Great guy but him being away so often meant it could never really last. I tried so hard and got so far, but I guess in the end it doesn’t even matter – I’m happily married now with 2 beautiful kids.
Image source: KENDRICK–LLAMA, chesterbe
#2
Not really “dating” but hooked up with Stephen Glover aka steve-o for a while when Jacka*s was first starting (i know it’s gross ok). He didn’t really have any money then and he was in between Florida and LA and needed a place to stay from time-to-time. He was very full of himself and we stopped talking after threw a chair out of my kitchen window. Good to see that he cleaned himself up though.
Image source: wayhe
#3
Teri Hatcher hit on me while I was delivering some legal documents to an office on the Universal Studios lot in LA. She totally did the double take thing and said “hey” as I walked by. I just ignored it, cause I’m gay and I was weirded out (but flattered). A few years later, I saw that she was dating Ryan Seacrest so I guess she has a thing for gay guys.
Image source: PM_ME_YOUR_DAD_DK, officialterihatcher
“The fame thing isn’t really real, you know. And don’t forget… I’m also just a girl, standing in front of a boy, asking him to love her.” Any ’90s rom-com fan will know the reference: it’s the iconic declaration movie star Anna Scott (Julia Roberts) makes to bookstore owner William Thacker (Hugh Grant) in the 1999 film Notting Hill.
Even if you haven’t seen it, you’re probably familiar with the trope. It’s practically a rom-com sub-genre by this point: a famous person and an ordinary person fall in love, and their relationship is anything but easy.
#4
Since there are so many comments this most likely won’t be seen, but I’ll tell it anyway.
My cousin dated Emma Stone right before she got really big. He even brought her to meet my grandmaw and his family. This was while he worked on The Help as a directors assistant. Proof. He has loads of pictures with her. He was also an extra in the movie which was really cool.
Image source: DoubleThink1990, imgur
#5
I dated Kristen Bell. She was just as cute back then as she is now. She is a great person. Things ended on her terms. I would have married her and only dated her for about a month. We went out a couple times, made out and such but didn’t go too far.
Image source: nalwb, kristenanniebell
#6
I dated an NHL player.
It was fun/weird. I was 21 and he was in his late twenties, seemingly happy to have a young girl to spoil. Going out was a lot of fun, but as you may guess about professional athletes, he wasn’t confident about himself at all and the cockiness was over compensation for low self esteem.
He also wanted me to call him daddy in the bedroom; I obliged.
Image source: optimusreim34, Getty Images (not the actual photo)
We’ve seen it play out in countless movies over the years. As Olivia Singh writes for Business Insider, “The dynamic usually follows a familiar arc. First, the normie is dazzled by the celebrity and their fame. Then, outside forces like the paparazzi or fans threaten to derail the relationship.”
Versions of this story have played out in real life, too. But while love usually prevails in movies “because rom-coms need happy endings,” Singh explains, some of the most famous real-life examples remind us that these seemingly fairy-tale romances don’t always come with a happily ever after.
#7
I was engaged to Rickey Medlocke lead guitarist from Lynyrd Skynyrd previously lead singer of Blackfoot. It was probably the best five years of my life!
Was able to attend the 2005 Grammys, walked the red carpet. Met some amazing people…. Hung out with Billy Bob Thornton (who is so down to earth and personable) ZZ TOP, Ted Nugent, Keith Urban (one of my favorite musicians so talented). I had the pleasure of being part of the Skynyrd family for many years which was a treat in itself.
Billy Powell was the sweetest man…. It broke my heart when he passed. I remember Gary Rossington telling me a story regarding the plane crash…. He remembered coming to with a piece of the wing on top of him. He was crying out for help when he said Ronnie walked up and told him to calm down that he was going to help him and proceeded to lift the wing off.
Gary said he passed out and woke up in the hospital wanting to know how Ronnie was. Apparently Ronnie had di*d instantly. Instant chill bumps.
As for the relationship: I was so lonely at times since he was touring almost all the time. I went on the road as much as possible but I had kids and a job so it wasn’t always feasible for me. I broke up with him :( He truly was an amazing man and for once in my life I “felt” loved. I had some friends who introduced him to the back up singer for kid rock Stacy Michelle. Apparently he didn’t take the break up well but him and Stacy are a much better fit and are still together to this day.
Image source: lilies2sons, Petty Officer 3rd Class Dion Dawson
#8
My sister dated Robert Downey Jr in 1998 while he was in a d**g treatment program with her.
Image source: Lillixsim
#9
My girlfriend’s aunt dated Bill Nye for a while, several years ago.
Image source: Drunk_Wizard, billnye
But that hasn’t stopped us from being fascinated by them. In March 2026, for example, Ryan Murphy’s Love Story: John F. Kennedy Jr. & Carolyn Bessette became FX’s most-watched limited series ever on Hulu and Disney+.
Based on Elizabeth Beller’s Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, the series revisits what Vogue’s Olivia Petter calls “the intoxicating relationship between two of America’s most beautiful—and famously doomed—people.” In doing so, it chronicles Bessette’s path from a private citizen working with VIP clients at Calvin Klein to the wife of a former president’s son.
#10
Not going to say her name, but in high school I dated a girl who is now a pretty popular guitarist/singer. She was beautiful (and still is), kind, and all around awesome. The problem was, she was a d*e hard Christian, and when I came out as atheist to her, she broke up with me. I understand it though. She was fine with having s*x though, but admitted that she faked her orgasms with me because she didn’t want to disobey god :/ I still don’t really get it.
edit: she’s popular, but not nearly as popular as some of the guesses you guys have made. she’s no real superstar, yet at least.
Image source: anon, Mariana Vusiatytska (not the actual photo)
#11
I f****d a now fairly well-know (in Ohio, at least) newsperson when we were in college on the regular. Wouldn’t really say we dated, but we hooked up a lot over the course of a few months.
Ended fine. She was fun and very career driven and focused. We just sort of stopped hooking up. For a while when I’d see her on billboards it was fun to tell people I hit that.
Image source: iMakeItSeemWeird, Getty Images (not the actual photo)
#12
D**n! Too late for this one but my mom dated Louis C.K. back in high school. Said he was a bit awkward, nice guy. Funny enough, took her to a comedy club on both dates. Tried to win her back later on by baking her a pie, didn’t work though I guess.
Image source: Made_at0323, Jimmy Kimmel Live
As Sarah Hunter Simanson writes for HuffPost, the series aims to “show how complex a figure Carolyn was” and explore “how the complicated love between the two unraveled under the pressure of the paparazzi and the expectation of being a Kennedy.”
That tension is highlighted across several episodes. In one, a colleague of Bessette’s explains, “She knows if she marries him, that will be her defining characteristic. It will be like she never existed before she met him.” In another, Carolyn says that she chose John “in spite of his life”—a line that gets at the complicated reality of falling for someone whose fame comes with a life of its own. Or, as Simanson puts it, “the tension that exists between choosing a person and choosing the life that comes with them.”
#13
I have a friend who claims (with some validity) to have dated Taylor Swift for 2 weeks in the 8th grade.
We tend to assume he is the subject of all of her breakup songs and blame him for her roller coaster love life.
Image source: discipula_vitae, taylorswift
#14
I shared an apartment with Jennifer Lawrence for 2 months before she realized I was living there.
Image source: Dat_Nia_Dbizzle, The Tonight Show Starring Jimmy Fallon
#15
I once shook hands with Adam Baldwin. He sorta grabbed my hand funny so i ended up giving him a really weak handshake, after our interaction i said ” hey sorry bout the weak handshake, you sorta grabbed me funny” and he looks me in the eye, puts out his hand and says “try again”. i grabbed that mans hand like my life depended on it, we shared a stern look and i went on my way.
Not exactly dating but it has all the right parts for a relationship (shame, fear, manliness
Image source: poopycocacola, Genevieve719
Watching the series unfold, it’s hard not to wonder how different Carolyn’s life might have looked if she hadn’t chosen John “in spite of his life.” And perhaps that same curiosity—about what could have been—helps explain our fascination with people who have had their own brushes with celebrity romance.
Sure, we like hearing unfiltered stories about what famous people are really like IRL. There’s something irresistible about getting the inside scoop from people who knew them intimately—stories that can feel far more revealing than any glossy tabloid account. For some, there may also be an aspirational element to hearing from ordinary people who crossed paths with someone famous—or someone about to be famous—and fell for them (or came tantalizingly close to doing so). But sometimes, the more intriguing part is imagining how different both their lives might have looked if things had turned out differently.
#16
I’ve posted this before – but when I was 14 I used to make out with a 13 year old Kristin Cavalari a handful of times.
She was a pirate.
Image source: SalteeWaltee, kristincavallari
#17
Rachael Ray farted next to me at an airport terminal during a layover in CVG, so I guess you can say we kind of dated.
Image source: pighalf, rachaelray
#18
I met a girl that dated the lead singer for modest mouse when they were still a college band (though still regionally famous). We started chatting online after we met. Got super close. She was basically cheating on him with me. She sent me tit pics while still dating him. I guess it wasn’t as fun as it sounds.
Tl;dr lead singer of modest mouse and I are Eskimo brothers.
Image source: PM_ME_UR_PANTY_COLOR, Dankstick
#19
I side-hugged Tom Hiddleston
He smells like Vanilla.
Image source: LightningMaiden, twhiddleston
#20
I had a thing with an NBA player. He was totally normal really, despite him being a big name. It was mostly a casual thing. We met at a bar and I was the only girl not trying to climb all over him so we ended up talking about our favorite Fantasy Football players (he hooked me up with some great tips for my team). Eventually he just turned into a superstar so we don’t really talk anymore- but there’s no ill will. His name sounds like dessert. Always made me hungry.
Image source: One_Sensual_Camel, Getty Images (not the actual photo)
#21
I dated Mireille Enos back in high school. She was set on being an actress even back then. I am happy for her and her success, plus she’s married to Alan Ruck (aka Cameron from Ferris Bueller) which is awesome and they just had their second beautiful child. She was and is one of the sweetest people you will ever meet.
I speak to her once in a great while when she comes back home to see her family. I did get to have dinner with her and her husband many years ago as we are still family friends with her family here. Great time.
Image source: KlerBeeTX, iammireilleenos
#22
Admittedly not answering the question, but tangentially interesting story…
My roommate from college’s mom dated a guy who was a musician, and dumped him for the guy who she eventually married (my roommate’s dad). The musician she dumped wrote a song about it.
Her name is Marianne. The song is “More Than a Feeling” by Boston.
She said he was a good guy, but felt at the time he was pursuing an unrealistic dream of being a musician.
Image source: madshm3411, Premier Talent Associates (management company)
#23
I dated Joel Zimmerman (Deadmau5) for about 10 months in 2005. He was living with his mother in Niagara Falls at the time, waiting for his visa to be approved so he could move back to California. He had already travelled through Europe at that point and was famous there, but not yet in North America. He didn’t drive, so I always did lol. Great times. One of the most intelligent guys I’ve ever met. Even though he comes off as an a*****e, he’s a straightforward guy.
Image source: anon, STERLING SPENCER
#24
Dated a ridiculously hot (and rich) Korean girl from LA that was in law school with me. She hooked up with Christiano Ronaldo and went on a few dates with him a few years before we dated. If I remember she said he really wasnt that good looking and she had no idea who he was at first – all of her friends were completely freaking out and she was just telling him to back off. She said his hair was ridiculously greasy – she wasn’t a fan. Also, Jim Carrey apparently tried to hit on her and she said he’s the creepiest freaking dude ever. The latter one I believe for sure, think I’ve read several times that Jim Carrey creepily hits on hot asian girls quite a bit?
Being eskimo brothers would Christiano Ronaldo wouldnt be the worst thing in the world.
Image source: anon, Takuya Hozumi (not the actual photo)
#25
A friend I met through sport had dated Mel B’s (former spice girl) daughter for a bit. He was telling me when he wen to her house once that they sat on a lounge with a security guard looking on and yeah thats pretty much it. They didn’t last too long together.
Image source: anon
#26
Not me but my neighbor (thats right, a woman), used to date Stevie Nicks, a lot of c*****e was consumed.
Image source: thebageljew, stevienicks
#27
Yay! I got one!
My aunt dated Montell Jordan for a long time until he cheated on her and left her. Hes currently married to that woman. She went all s******l after that for awhile but she did get a kid out of it…not sure if it’s his but he kinda looks like him.
Anyway, she moved back to her home state, got a house built for her and her son. She’s still single and doing well!
Image source: redheaddreadhead, montelljordan
#28
My stepdad’s cousin dated Woody Harrelson in college. He pursued her for two months, following her to classes, leaving weird notes on her dorm hall corkboard, and calling her every day with Bible quotes. She finally went out with him, and ended up taking him to Thanksgiving with her family. Her dad thought he was “a no good piece of s**t slacker”. They broke up just before Christmas; they were both cheating on each other by then anyway.
EDIT: Now that I’ve read the infamous AMA, it rings a few bells. Apparently Woody didn’t like to talk about things he didn’t bring up himself, most especially his family and his dating history.
Image source: sweetalkersweetalker
#29
I dated Brian Warner (aka Marilyn Manson) before he was famous. He wrote me really bad poetry and drove a Fiero.
Image source: Sentient_handbag, Andreas Lawen, Fotandi
#30
My great aunt dated Alex Trebek back when they were teenagers. My grandfather did not think much of him; says he didn’t think the guy would make it very far in life.
Image source: melorun, Nestor Cruz (U.S. Air Force)
#31
My aunt dated Jimmy Fallon in the 90’s before leaving him for my uncle.
I love my uncle to d***h, but I’d be lying if I said I wasn’t disappointed. Jimmy’s one of my favorite comedians.
Image source: kigurumiadct
#32
I worked on Gilmore Girls as an extra. Then one day Alexis Bledel walked past me and said, “Hey.”
And I replied back, “Hey”.
So yeah, I guess I could say that’s as serious as that ever got.
Image source: Spider_Dude
#33
She ditched me for a much better looking guy who was a year older. Jokes on her now though; she won an Oscar and I’m doing kind of ok.
Image source: anon
#34
Grew up with Tracy Spiridakos (Charlie from Revolution)
Kissed her once at a party so that counts right?..lol
She’s a really cool person albeit a little snobby.
Image source: Womp2
#35
Dated Gabbie from the “GabbieShow” and SoFlo on Facebook/vine when we worked for a marketing company called smart circle. Shes got a big a*s and a big crazy ego to go with it. Good luck to anyone hittin that. She ended up f*****g my buddy because he payed “more attention” to her LOL.
Edit: No I do not have contact with her anymore, no I do not have her number. I didn’t even get a reply back to me congratulating her on her new found success a couple years ago. There’s that ego for ya.
Edit 2: We worked in a Sam’s club together, I pushed DirecTV like it was crystal m**h at the time and she sold a different emerging product each month, both for a company called Smart Circle, and she was actually a good salesman and was very personable.
Image source: anon
#36
Minor celeb, but her band’s been on MTV. We dated for a month or so, but we just didn’t connect personality wise or see each other much with different schedules.
Image source: trebuchetfight
#37
My time to shine!
I went spent some time with the One True God himself. Yes, Nic Cage. We spent an evening together (not a night, I declined) and he asked me out the next day. This was right after his split with Lisa Marie Presley. We kissed and talked. He is actually a really fascinating person.
And, yes, I get endless s**t about this from my younger friends. But, whatever, he was hot and I had a crush on him before we met.
Image source: Throwitaway011001100
#38
I’ve dated two, one went on to be a musician, and one a prominent radio personality.
The musician was a fling, lasted a few months and we mutually parted ways on friendly terms. He was very funny and competitive in bizarre and creative ways. He later went to Berkley School of music and now he and his band tours the U.S. and Canada last I heard. His music is good but I don’t listen to it because, I dunno, it feels awkward?
The other one was a local radio DJ who did a top-40/rap station here, but his real passion was the band Pearl Jam, he f*****g LOVES that band. He was very cerebral, and we had lots of philosophical discussions. He had me do radio spots (commercials, etc) because he said I had a good voice for it. I later ended up doing things for other stations after we broke up. He broke up with me because I was 19 and he was 28. I was still living at home then. He now hosts a popular radio show in Los Angeles.
Both are still good people, neither have become jaded, washed-up a******s, or so the grapevine says here.
I am now happily married to a non-celebrity.
Image source: FireEagleSix
#39
I met a girl in on the late 80’s. We lived in Texas. She was 16 and wanted to be an actress, I was 18 and had no ambition. We dated for a few years. She was discovered by playboy magazine during a spring break trip shortly after turning 18. We moved to LA and she was in almost every face soap, tampon commercial. She did a few tv shows and starred in one teen movie. We broke up when she decided she liked long haired guitar players. We remained very good friends for years after the breakup. She got married and divorced to a different guy. He and I are best friends and neither of us speak to her anymore. Last I heard she was living in a s****y apartment and still trying to get famous. She made a lot of money for a few years in the mid 90’s but she’s past her prime now.
Image source: Jaybirdmcd
#40
My grandmother went to prom with a supreme court justice (Anthony Kennedy) and she still can send him emails and he will answer. I guess that counts.
Image source: easyR
#41
My Girl Scout troop leader dated Johnny Depp in high school, if remember correctly. I doubt they dated long; she said he was strange. She had pictures of them together and year books and junk. We all thought it was so awesome and were wondering which kid in our elementary school was destined for fame.
She canceled our meeting one week to go to his wedding. She was cool.
Image source: sugarminttwist
#42
My dad went to high school and wrestled with Axl Rose. I wouldn’t consider that dating but there was a lot of touching and hugging.
Image source: Sunnyboy451
#43
Steve Jobs f***s me over everyday with itunes, does that count?
Image source: anon
#44
I wish I had more to this story, but, I met katy perry back when I was a touring musician and she was a solo act, and she told me I was really cute and we drank all night and I wussed out of doing the deed because I had a f*****g s****y girlfriend back home. Years of regret, and unrelented taunting from coworkers.
Image source: frontbutthole
#45
Hooked up with Ke$ha at a high school party. No details really. Just a hook up at a party.
Image source: PM_ME_UR_TS_THNX
#46
Got a novelty kiss out of Zooey Deschanel when I worked with her on set once. Like, I got the whole staff joking about how romantic it would be for the lighting assistant to kiss her. I made it a running joke. It got around to the whole cast and even the interns. On the second to last day, I got the kiss. You could say we’re pretty serious I guess.
Playing the long game, guys. It works.
Image source: PM_ME_UR_TS_PLS
#47
This is going to buried for sure, but I currently date a guy who is a drummer for a major band out of Boston, has a Billboard Award and an international hit song.
Its…interesting. We’ve been together for two years and for the most part it is a pretty easy relationship. He and I are both homebodies and he’s not very social (after shows he usually hides in the backstage area), but we both enjoy road trips and that is where we spend our money (or video games and music equipment (thats more him)). I do very well being alone so when he’s on tour for weeks I am okay; of course I miss him, but I’m able to cope, and he does his best to always keep me in the loop or let me know he’s thinking about me.
One negative is planning anything with him is almost impossible. He rarely knows where he is going to be or if a show will pop up, if he has to take a last minute flight to LA or NY, or what have you. I am very much a planner, and he will usually tentatively agree with things, which is nice.
All in all it is a pretty typical relationship with the perk of awesome backstage access.
Image source: belethors_sister
#48
I went on *a date* with Nick Swardson. Very normal and sort of funny. He had to leave earlier to catch a flight and paid for me to have dinner by myself.
Image source: hamplanetstrip
#49
My grandmother dated Marshall Mathers Sr. in high school. She said he was a really nice guy.
Image source: anon
#50
Olivia O’Brien, who wrote “I Hate U I Love U” went to my high school. She was a year below me, but we were super close friends. One day, however, we were hanging out alone on a road in Napa and one thing lead to another, and we made out in my car. The next day, I was hanging out with a different girl who liked me and we, well, did it. So me and girl number two ended up dating. Olivia was heartbroken, and actually wrote her first version of “I Hate U I Love U” (the original is still on her SoundCloud profile, honestly really good looking back on it.) Thing is, Olivia is crazy, and can be a huge b***h if you get on her bad side. She made my life living hell with my girlfriend, and was one of the reasons we broke up in the long run. Eventually, her and this Gnash dude meet up and do the collaboration for SoundCloud that now has a few million listens or something. She was a little bit of a local celebrity but hadn’t blown up outside of our town yet. Her and I actually made up, but she left our school and now lives in LA recording new music and I haven’t heard from her in a long time. The thing is, she was such a sweet girl and I feel horrible for playing her the way I did, but she’s still super crazy. Either way, she’s famous now, and I’m studying in college. She’s successful in her way, but I wanna be successful in my own. How I hurt her in the past and where she ended up because of it inspires me to be a better person and to see the light at the end of the tunnel.
Image source: Bbrazil97
#51
Met a guy in an up and coming band first year of college. On and off for years bc I didn’t want to date a guy in a band, plus he had dropped out of college to pursue his career and that seemed short sighted to me. Fast forward a couple years his band is winning VMAs. Fast forward a couple more there are very public issues. Fast forward a few silent years and they’re bigger than they ever were. Still the same sweet generous loving man I met we just now have a bigger, better, more blessed life than I knew was even possible when we first met. Entertainment industry is super weird and fickle. There are times I wish I married an accountant, teacher or lawyer for the stability but I honestly wouldn’t change it for the world. At this point the craziness is all we know.
Image source: myneighborsucks69
#52
When I was 13 I kissed 17 year-old Mary Kate LeTourneu (Schmidt). I wish I knew.
Image source: fannygas
#53
A few years ago I f****d a then-rookie NFL player who now starts for a fairly impressive AFC team. To me, the s*x was nothing special and I chalked it up to another kind of cool f*****g story. He must have felt otherwise because I spent the next few months avoiding his calls and texts.
Yes, I now realize that if I would have accepted his advances I would not be living in the s**t hole apartment that I am currently typing this from. But, I realized something more important back then…even 300+ lb. linebackers can have very, very, tiny d***s.
Image source: faded42out
#54
Knew ray fisher (cyborg) for a long time. hooked up with him one night. he’s a great dude.
Image source: thr0wit4llawayy
#55
Aunt was engaged to Steve Madden. She ended it and actually managed to marry up financially. Married a billionaire…it’s ridiculous how much money her husband makes.
Image source: mrsdwright5
#56
Wasn’t me, but my dad went to high school with Ricki Lake. They messed a round a bit according to him, he also broke her nose in gym class while spiking a volleyball, so I’m sure it didn’t go that far.
Image source: JWillsNH
#57
I dated Kylie Jenner. Not really allowed to discuss, but she’s a very very cool person.
Image source: Mike101111101010
#58
I cybered with a redditor before they hit 10k karma. Sadly we lost touch when they became a moderator and went all hollywood on me.
Image source: stillnoxsleeper
#59
My mom dated slash in high school. Before she passed away she joked with me and tells me ” d**n, why couldent he be the father”. I laughed so hard when she said this. She was also friends with Mikey from OCC.
Image source: lastx1xstanding
#60
My boyfriends sister used to date Justin Bieber’s dad. He’s a huge d*******g. No surprise there.
Image source: whiskey_river
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