20+ People Who Didn’t Realize They Were Going on a Date With a Future Celebrity

When we look at celebrities, we get this perception that they were born famous. But very few people become an international sensation in their childhood (except for members of the royal family). Celebrities used to be ordinary people who went to their proms, had fun with their classmates, and hung out at local pubs. And many people who were lucky enough to go out on a date with them, are now kicking themselves for missing such a good opportunity. Well, at least they have a fascinating story to share.

We at Personal Gain found stories about the people who used to date world-famous celebrities. And they can shed some light on how our idols behave in their everyday lives.

My aunt lived on the same street with Leonardo DiCaprio when she was a kid. He was the first boy she ever kissed. It happened in the school gym when my aunt was 12 years old and DiCaprio was 13. As far as I understood, he was a really nice guy. My aunt lost touch with him when he started to play the leading roles in movies. © andyjams / Reddit

I went on 2 dates with Emilia Clarke about 5-6 years ago. She was really witty and sweet. Things didn’t work out between us (obviously) but I wish they did. © throwawaySPB / Reddit

My mom turned down Brad Pitt in a bar in Ireland. He had just landed his role in Thelma & Louise, so he was only really known for his Levi’s ad. But my mom had no idea who he was. He asked to buy her a drink and she declined. He told her about being a Levi’s model and she declined again. Now she feels really sorry about that. © juno-f / Reddit

My friend went on a few dates with Natalie Portman when they were both at Harvard University around 2002. He said she was genuine, exceptionally down to earth, and very engaging. © ICanhearyou4444 / Reddit

My mom had a dinner date with George Clooney in the 1990s. She didn’t really say much apart from the fact that he’s an interesting and charismatic guy. She honestly didn’t think he was going to get really famous. © NardClump / Reddit

My boyfriend went on a date with Rosario Dawson. They met via a mutual friend. So now every time I feel like I’m not attractive enough or we get into an argument, I just yell: “Why don’t you go back to Rosario?!” © Unknown author / Reddit

I have a family friend who dated Daniel Radcliffe. I was 7 at the time when they dated, and a huge Harry Potter fan. I don’t remember much, aside from the fact that he was a really sweet guy. On my 8th birthday, my family friend asked Daniel to write me a personal happy birthday message despite having never met me. And he did! Absolutely made it the best birthday ever. © eveisannoying / Reddit

My dad took Kylie Minogue out for the drinks a few times in London. It seems like they couldn’t make it because there was too big of an age gap. © Unknown author / Reddit

My friend’s sister-in-law was out jogging when some dude came up and started jogging with her. They talked about random stuff like a movie being filmed nearby at that time. After a bit of that, he said: “Oh, by the way, I hope you’ll like the movie.” They were filming “Star Wars: The Force Awakens” and she only realized later that it was Harrison Ford. © s-exorcism / Reddit

My cousin dated Jamie Lee Curtis in college. He said she was very nice. They were together for a while. But once college was over, they headed in different directions. © TipToeThruLife / Reddit

My mom dated Keanu Reeves back in high school. She broke up with him because he was too focused on his band with his friends at the time. Oh, if only… © takedownhisshield / Reddit

My sister went on a couple of dates with Vince Vaughn when he was filming The Break-Up in Chicago. She said he was nice and kind of goofy. She stopped hearing from him because he started dating Jennifer Aniston. © Bilfres43 / Reddit

My friend turned down Jennifer Connelly. In the mid-80s, she spent the summers in a small town on Long Island. This was after she was in The Labyrinth but before The Rocketeer. Their parents were friends somehow, so she would hang out with a local circle of friends. One evening she asked him to go on a walk and he said no. He is still made fun of for it to this day. She was very nice by all accounts. © DarcizzleOffshore / Reddit

A friend of mine dated Brad Pitt in college. They went on 2 or 3 dates, if I remember it correctly. I went to a different school, but I remember meeting him when I went to visit my friend. © Bluegirl1965 / Reddit

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 2 guys who were their age. The whole date, these 2 were talking about a script they had written and how it was going to make them famous. Afterward, she and her friend decided that these guys were pretentious and kind of annoying. Those 2 guys were Ben Affleck and Matt Damon. The script? Good Will Hunting… © WellNobodyToldMe / Reddit

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. © twistlock / Reddit

I dated Jennifer Lawrence in 2008. I met her at a yoga class in Santa Monica. I had no idea who she was when I met her. I just thought she was cute and I started talking to her. She said I shouldn’t watch a lot of TV, and that she was on a crappy show on TBS. She ended up giving me a ride home from the class, and then I asked for her number. We went out a couple more times after that, but soon I learned that she was only 17 at the time. But it was cool to get to know her anyway. I lost touch with her after a few months since her career was starting to take off. Now it’s kind of a trip when I see her in movies. © supabass18 / Reddit