25 Times People Met Celebrities And Walked Away With Weird Or Embarrassing Memories

Published 1 month ago

In the vast landscape of the internet, where communities thrive on sharing anecdotes and experiences, Reddit stands out as a hub for storytelling. Recently, a captivating question surfaced on the platform, sparking a wave of engaging responses: “What’s your most awkward encounter with a celebrity?”

As Redditors from around the globe poured in to share their tales, a fascinating tapestry of awkward, humorous, and downright surreal celebrity encounters unfolded. Scroll below to read some answers.

Read more

#1

Image source: anon

I was part of a college press circuit doing a group interview of the stars of Death To Smoochy.

At the end of the whole thing, which took place in a hotel in L.A., I was waiting for the valet to bring my car up. Prepared for this, I had a five dollar bill folded and palmed, ready to give a tip. Next thing you know, Robin Williams came out to wait for his SUV, we made eye contact and he went to shake my hand. Starstruck and forgetful of my fiver, I shook his hand and slipped it in his. He just stared at it for a second, looking at it, then back at me, then back at it, and had a look on his face akin to “You want me to tell a joke or something?” We had a good awkward laugh about it and parted ways.

By the way – if you get Robin Williams and Danny DeVito in the same room together, be prepared to have your abdominal muscles hurt like hell the day after from laughing so hard.

#2

Image source: anon, Entertainment Tonight

Back when Avril Lavigne was newly famous, I was walking to the Art Gallery of Ontario in Toronto. There was a woman in front of me with her a**-crack hanging out, wearing punk clothes. I said to my friend: ‘Oh, look: It’s another f**king Avril wannabe.’ The woman turned around and shouted: ‘I AM AVRIL!’ And it was.

#3

Image source: ouch-that-hurts, disney

I hurt Han Solo’s feelings. I was walking down 3rd St. Promenade in Santa Monica, and my girlfriend looked up and said: ‘Look! There’s Harrison Ford over there!’ I looked up and said I didn’t see him. My girlfriend pointed adamantly and loudly: ‘Over there! It’s Han Solo!’ My response was: ‘What — that old guy?’ at which point Harrison Ford looked directly at me — he had heard. His face dropped, and I feel bad to this day.

#4

Working on a reality TV show filming at Sundance. Went to a party in the evening hosted by Sting and at some point went to the bathroom and started to use the urinal. Mid-p**s someone pushes in next to me, literally pressing me out of the way and starts pissing in the same urinal. I’m thinking “who the hell does something like this?” I look up and meet eye to eye with a rather inebriated Sting.

So yeah, crossed streams with Sting when I crashed his Sundance Party and missed the opportunity of a lifetime to tell Sting not to stand so close to me.

Image source: cyclejones

#5

This one comes from my friend’s Dad, who is an academic who travels a lot for his job.

One day, when returning from a conference in Sydney, he is waiting in the business lounge when he spots a familiar-looking man. He racks his brains trying to figure where he knows him from, and decides to go over to find out (it would be rude to ignore him).

Prof: Hi, you look awfully familiar. Were you at the conference this week for International Trade Law?

Man: Uh, no, I wasn’t.

Prof: Oh, we have definitely met before though. I’m Professor ***, from X University?

Man: Um, I don’t think we’ve met.

Prof: I definitely know you. Are you in law?

Man: No, I’m not.

Prof: Well, I must have seen you at a conference somewhere. You’re American, which university are you with? Or your colleagues, maybe you have a supervisor I might recognise the name of…?

Man: …I don’t work at a university.

Prof: Well, what is your name at least?

Man: Matt Damon.

facepalm

Image source: not_a_frog

#6

Image source: tdasnowman, Conan O’Brien

I used to work event security, I was working backstage at a N-Sync concert. Now they had been there all day, multiple sound checks they put in work before a show. I also had barely any clue about the groups playing that night. So nice car pulls up out pop a really attractive blonde, big body guard next to her. Body guard is carrying 2 backstage passes so I just hit them with a polite can you make sure you’re wearing them the bands have arrived. Dude flashes me a look, the girl just says ok smiles and waves. Few minutes later my boss comes out with the principals sheet. I just asked Brittny spears to wear a backstage pass. Boss thought it was hilarious I’d told him multiple times I didn’t listen to pop music I have no idea who the people are I don’t think he realized till that moment how serious I was.

Little more. N-sync had been there all day. We were on station at 5:30 and the tour bus was already there. Us backstage guys ended up interacting with them quite a bit. So when they left and JT gave me a signed backstage pass I thought nothing of it. Just a nice little thanks for throwing the nerf ball with us. Wasn’t till I showing it to a friend of mine she noticed Brittany signed it as well. I had no clue they were dating. Maybe a little shade in that gift.

#7

I saw Mel Gibson in Rome when I was in high school (before he went crazy, or at least before the public knew) He was eating at a sidewalk cafe. I meant to just wave but for some reason blurted out “Braveheart!” A bunch of people turned and recognized him. Angered with the attention I brought to his lunch he glared at me with a look of such hatred I thought he might actually get up and come after me. Just then, my Grandmother walked right up to him and snapped a picture of him point-blank. I kinda felt bad for bothering the guy until years later he revealed himself to be a racist, sexist alcoholic.

Image source: leftistesticle

#8

Image source: Fuzzykittenboots, Pixabay

I was at a large book event and I had picked up a book and stood in line to pay. Or so I thought. Turns out I was actually standing in line to a book signing with a very famous author. The one I had picked up was not by him.

#9

Image source: thegnome54, Warner Bros. Pictures

A group of my friends were eating at a dining hall at the same university Emma Watson went to. One of them started excitedly describing how she had spent her break rereading the Harry Potter books — as she was talking about all of her favorite parts, Emma Watson sat down in the booth directly behind her. My friend didn’t notice, but the people across from her did. They goaded her into continuing this line of discussion for about 15 minutes before Emma finally got up and left. My friend was mortified.

#10

I once had a conversation with Colin Firth about asthma and carpets (I learned that his wife is asthmatic).

He was pretty chill tbh. I am a dwarf so I’m used to people being awkward around *me* more than anything but he was pretty much exactly how he is on screen.

Stephen Merchant on the other hand actually signed his autograph for me while using my head as a writing surface, that guy is bold as brass lol, but I loved it. It’s refreshing to meet people who don’t walk on eggshells around me. I wouldn’t be surprised if his time with Warwick Davis had desensitised him.

Image source: Usidore_

#11

Image source: thepizzlefry, nbc

I was visiting New York City and walking around with friends — it was pretty late, but the streets were still bustling. We walked by a group of people crowding by this building and asked them what was going on. Well, it was the GE Building (30 Rock, if you will) and Saturday Night Live just ended. The people were waiting to get their picture taken with the cast and get an autograph. Just as this was being explained to us, Tina Fey walked out (this was before 30 Rock, so she wasn’t as famous yet — but she was my favorite member of the SNL cast at the time). So, I eagerly asked her for a picture. She’s fairly small and I’m a pretty big guy, so I thought the picture would be hilarious. Well, just as we were taking the picture, I accidentally stepped on her toes really hard. I was apologetic, but she was clearly (and rightfully) unhappy and walked away. The picture was just her grimacing in pain.

#12

Back in 1990, I was staying at a very expensive hotel in San Diego. Early one morning, while waiting for my wife to get ready, I went down to their patio area facing the beach to drink coffee and read the morning paper.

I am sitting there, and from the corner of my eye I see a couple walking on the beach, coming toward me. Since it is early, me and the couple are the only people near the beach. I keep an eye on them as they get closer, over the top of my paper, until they are just about in front of me when I glance up.

Paul and Linda McCartney.

They are holding hands and walking barefoot. Paul smiles at me and Linda says “Good Morning”. I am so shocked that all I can manage to do is give them a weak wave and a “hey” before they stroll off.

I run back up to my room and tell my wife who: 1. Doesn’t believe me at first and 2. Chastises me for not asking for an autograph.

Image source: anon

#13

a friend saw christian bale at the end of the block. and my friend being very animated smile really big and was clearly headed over to him. Halfway there christian mouthed “don’t” and my friend left him alone.

Image source: anon

#14

I was at a bar in Hollywood tonight, and was talking with this girl. Another guy comes up, and it’s clear they know each other, and he joins in the conversation. After awhile, she talks about how her friend had her first concert not too long ago, and it was a Backstreet Boys concert. I laugh a bit at how a 27 year old has that as her first concert. The girl starts asking “Are you laughing about the Backstreet Boys? Don’t you know who this guy is? He’s a Backstreet Boy!” I don’t believe her at first, and say so. He then puts out his hand and goes “Hi, I’m A.J.” Sure enough, it clicked, and I was just laughing about the Backstreet Boys in front of a Backstreet Boy. He was actually cool about it, but def was a foot in mouth moment.

Image source: FunkyHenryGale

#15

Image source: feeling_groovy, ABC

When I lived in New York City, I used to live in the same building as Regis Philbin. It was July 2007, and I had just taken the Graduate Record Examinations for the first time. I did terribly (you get your scores right after the test is finished), and I was really, really mad. So, I decided to go to the gym when I got back to my apartment. I got home, changed my clothes, was still fuming, and got in the elevator (keep in mind that I was still in a terrible mood). I had to fart really badly and was just like: ‘F**k it. Who cares? I failed my GRE, nothing can be worse.’ So I let one rip, and it remains one of the most foul farts I have ever released (I mean, rotten-egg smell). It made my eyes water. So, I am in the elevator alone choking on my own fart when suddenly the elevator stopped and opened, and who should get on but Regis Philbin. My fart flew at him and engulfed him, and I had no one to blame it on — it was obviously me. I was horrified, I turned bright red, and ran out of the elevator. So, yeah: That is how I met Regis for the first time!

#16

Met Charlie Sheen at a nonprofit event during his peak wild time. He brought his fiancé. I was the person sent out to greet them and bring them to their seats so they could get in without being stopped by other attendees.

Me: Hi Charlie, I’m here to take you inside and direct you to your seats

Charlie: Hi. What’s your name?

Me: Carly, nice to meet you

Charlie: …stares blankly like I’m an enormous idiot…no, *I’m* Charlie. I asked for *your* name

Me: uhhhh, it’s Carly. Like your name? With no H? (at this point I’m starting to get really anxious about having him standing outside for too long and just want to get moving)

Him: Ohhhhhhhhh. Righteous (flashes peace sign)

And then he let me lead them inside. I was an absolute wreck for that entire event but he was incredibly well behaved for the whole thing.

Image source: carlyv22

#17

Image source: Unun_Pentium

Standing in front of a hotel with Will Ferrel, awkwardly looking at him recognizing that I recognized him. He was cool though…I however was not.

#18

I was with my ex-girlfriend having ice cream before going to a comedy club in northern Kentucky, when this petite woman walked by with a couple of women. We watched her go by and I said: ‘That woman looks like Natalie Portman.’ She sat down at a table nearby and I looked again (it’s important to know I have an enormous crush on Natalie Portman because of the Star Wars movies). In fact, my ex and I came to an agreement that I wasn’t allowed to cheat on her unless it was with Natalie Portman. So, I started to slightly freak out, calmed down eventually, and went over to ask Natalie if she was indeed my biggest celebrity crush. I gave her the usual ‘big fan’ praises, then excused myself so as not to disturb her when she was enjoying a night out with her family. Later while we were waiting to be let into the comedy club, who should appear right behind us in line but Natalie f**king Portman (she had the same plan as us). “We were assigned to sit at the table right next to hers, and several times during the night she accidentally leaned back against me. It felt bizarre and surreal, because what the hell was Natalie Portman doing in northern Kentucky sitting next to me?! Anyway, the awkward part was that the comedy club did a forced audience participation bit where they grabbed a random person and yanked them onstage to play a part in a sketch. Of course they grabbed me, so just try to imagine performing in front of an actor you’ve had a crush on for about a decade, and you’ll have an idea of the kind of star-struck anxiety I had while I was there. The performers had the foresight to realize that an unwitting addition to the troupe would likely be awkward and confused, though, so I fit the part pretty well.

Image source: faschwaa

#19

Mike Tyson at the Bellagio sea food buffet. I was inebriated and piling a plate super high. I was also eating food off the plate as I walked around the buffet. Suddenly I looked to my left and said with my mouth full:

“eeeeeh, you’re Ike Typhon.”

He looked at me like a crazy person and walked away.

Image source: Radio_Edit28

#20

Image source: Sauce_________, piercebrosnanofficial

My mum was at the airport browsing the newspapers at a kiosk and some guy reached past her head really close to grab something. He said sorry and took it to go pay. My mum was a bit annoyed until she saw it was Peirce Brosnan.

#21

Image source: MySFWTransAccount, Apple TV

Was at a funeral with Stevie Wonder for a mutual acquaintance, and my dad awkwardly went up and was like “Um, Mr. Wonder, I love your music, it affected my life a lot when I was younger,” and it was just painful.

#22

Image source: irregaardless, Tony Schnagl

Met my favourite hockey player. I was very flustered. And so i turned to him and said “soooo….do you like hockey?”

What a pick up line.

#23

Image source: anon, cubagoodingjr

My family was actually in Hawaii when Pearl Harbor was being shot and Cuba Gooding Jr. was staying in our hotel. The first night we went down to the pool and there he was in the hot tub with a plethora of hot women. Instead of the usual… “Hey Cuba! I loved Snow Dogs!” I said, “Aren’t you married?” I immediately regretted it. I wasn’t trying to be a douche :/ It just slipped.

Tldr; Cock blocked Cuba Gooding JR.

#24

Image source: gabeanator, netflix

I almost got ran over by Hugh Laurie. I glared at him, he held up his hands in apology, and we went our separate ways.

#25

Image source: Wisdomlost, jonbonjovi

Not mine but my ex wife once peed on Jon Bon Jovi. She was 2 years old. Her uncle did charter fishing tours and I guess he was into it at the time. They asked if he wanted to see the baby. He held her and she picked that time to pee.

Saumya Ratan

Saumya is an explorer of all things beautiful, quirky, and heartwarming. With her knack for art, design, photography, fun trivia, and internet humor, she takes you on a journey through the lighter side of pop culture.

Got wisdom to pour?

500-

Tags

awkward celebrity encounters, awkward celebrity moments, celebrities, celebrity encounters, weird celebrity encounters
Tweet
7
Like deMilked on Facebook
Want more milk?
Hit like for a daily artshake!
Don't show this - I already like Demilked