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Updated on Oct 9, 2019. Posted on Jan 13, 2019

18 People Who Knew And Dated Famous People Way, Way Before The Fame

"My sis use to date Usher in high school and she just now telling me this, smh."

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1. This person's mom who dated Adam Sandler long before his time on SNL:

2. This person's aunt who knew Bradley Cooper (and his mullet) back in the day:

3. This person who had a wonderful encounter with Jake Gyllenhaal as a kid:

"My fiancé fell off his bike when he was a little kid in LA. A nice boy aged 12 or so helped him up and walked him home to make sure he was okay. The nice boy was Jake Gyllenhaal."

SchleppyJ4

4. This person's mom who dated Matt LeBlanc before he was Joey:

@wtm_rachel / Via pics.me.me

5. This person's mom who dated Woody freakin' Harrelson:

6. This person who bonded with Kylie Jenner over animals:

"I was friends with Kylie Jenner from 4th to about 8th grade. We stopped talking because I left to go to another school. Honestly? Nicest person I’ve ever met. I was a chubby weird girl, and didn’t have many friends when I started at the new school. There’s even a group picture of us my first year all sitting on a hill, and out of everyone I was the only one sitting alone. On that trip, my mom came as a chaperone. She was walking with Kylie while I was some place else, and told my mom, 'I like Mauvemoth. I wish everyone wasn’t so mean to her. She is really nice. She loves animals, and so do l!' She then proceeded to meet up with me and talk about how cute this turkey was. She really helped me those years. She was one of the only people who didn’t bully me. We weren’t best friends, but when we did hang out, we had fun."

mauvemoth

7. This person's sister who dated Usher as a teen:

8. This person's aunt who dated Tupac ages ago:

9. This person who knew Chris Evans way before he was Captain America:

Chris Evans lived down the street from me and was my babysitter. His mom directs the plays at my town's high school. I haven't seen him since I was little, but when he was in high school he was just a normal dude. Nothing about him screamed, 'I'm gonna be famous one day.' It was just sorta, 'I'm good at this acting thing and it just so happens that people who are good at acting get famous.'"

SodomySeymour

10. This person's aunt who dated Ashton Kutcher long before Demi:

11. This person's wife who dated "The Fonz" himself Henry Winkler:

u/UberStone / Via reddit.com

12. This person who dated Kristen Bell and would have married her:

"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."

nalwb

13. This person's cousin who dated Matthew McConaughey in college:

14. This person's mom who had "a thing" with Blake Shelton years and years before The Voice was a thing:

15. This person who knew Henry Cavill and says he owes him a beer:

"Really nice kid. Shy and not as self-assured as some of his peers but this made him a very pleasant person to know. Don’t know him as an adult (last met when he was maybe 20) but would be surprised if he was so very different. He owes me beer."

fiveupfront

16. This person's aunt who dated Jimmy Fallon a hecka long time ago:

17. This person's best friend's mom who went to prom (?!) with Josh Duhamel and his mini-mullet:

my best friends mom went to high school with Josh Duhamel and found this in her yearbook. I think I see a mullet😂😂

18. And finally, this person who says Emilio Estevez was the sweetest:

Emilio Estevez was the absolute sweetest kid in high school. (Santa Monica High, 1979/80.) Took a physiology class with him and before we knew his dad was an actor, before he had fame as an actor himself, every kid I can remember liked Emilio because he was already a genuinely kind, grounded person.

WeFosterKittens

Note: Obviously we can't confirm that these stories are 100% true, but let's enjoy them anyway, mmkay?

H/T to Reddit for the text-only entries.

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