March 26, 2020 | Eul Basa

Waiters Share The Biggest Valentine’s Day Disasters They’ve Ever Seen

Valentine’s Day is an occasion for romance, wining and dining, and love. At least, that’s what we’ve all been led to believe. For some, Valentine’s Day is nothing more than the stage on which they perform one of their most awkward encounters. These waiters got ringside seats for some pretty memorable disasters. 


#1 Gloves Off

I once saw a couple have a full-blown argument in the middle of the restaurant. The woman stood up, actually took her ring off, threw it at her partner and then just walked out. The man continued his meal, even had dessert and then paid the bill. He also left me a pretty big tip for the inconvenience and left!


#2 Painful Small Talk

Two failed marriage proposals on the same Valentine's Day. The first one simply said, "No, I can't do this," and walked out. The second one stared like a deer frozen in the headlights for an excruciating 30 seconds before muttering "Let's talk about this later." They stayed for the rest of their six-course special dinner, eating and making painful small talk.


#3 Keeping Things Hush-Hush

It wasn’t disastrous for the couple as much as it was the restaurant. I used to work at a small southeastern franchise restaurant, it wasn’t anything you could mistake for upscale. We had someone call in and ask if we could fry the ring he was planning to propose with in a hushpuppy. Extremely weird request, but we said sure. They came in to eat with their families. She got her order of hush puppies, didn’t choke on the ring and seemed excited enough. They stayed at the table for about two hours total and chatted. They then dined and dashed.


#4 Second Glass

This wasn’t really a disaster, but this one guy came in and said he was waiting for his date. He proceeded to stay for five hours, just waiting, and she never showed. He eventually ordered a meal for himself and asked that I remove the other glass of water from the table. He then said that it was their first date.



#5 Just… Very Sad

We had a table of two people, probably in their mid-40s. It took 45 minutes for this couple to get their entrees due to our kitchen being slammed. When they were dropped at the table, they immediately asked for to-go boxes because they told their babysitter they’d be home by a certain time. I overheard the wife say, “Well, I guess this is why we don’t celebrate Valentine’s Day”. The worst part was that they weren’t angry, just… very sad. I felt so horrible that this couple clearly had put in an effort to have a nice night with each other only to have it go that way. (We covered their meals.)


#6 That’ll Show Her

I was working as a waitress in a sushi restaurant and Valentine's Day was an all-hands-on-deck shift. This guy I had just started seeing wanted to go out, but I told him that working in food service, you never get Valentine's Day off. I told him that we'd just have to celebrate the day after or the weekend after. Nope. He got so upset that he went and asked a different girl out, came to the restaurant I worked at on Valentine’s Day and sat in my section . He then proceeded to spend the entire evening making a fool out of himself and making his date uncomfortable as he tried to make me jealous. Needless to say, we didn't ever go out again.


#7 Center of Attention

I saw a couple have a full-on argument at a restaurant. I wasn’t their server, but the table was directly in the center of the restaurant and they were certainly loud enough for everyone to hear. My manager kindly asked them to leave and the guy’s response was to yell, “I’ve been wanting to do that for two years now.” Then, he stormed out.


#8 Like a Movie

It was like a movie. I was working at an Italian restaurant and it was pretty much full of Valentine's dates. A guy walked in and sat at the bar by himself, looking pretty down. He asked for a whiskey, so I poured it. I told him it was on the house because he looked like he needed it. He then proceeded to tell me his story.

He had come to the city to surprise his girlfriend for Valentines (about a five-hour bus trip between cities) and he sure surprised her. She was in her dorm room with one of his friends from high school. He didn't know what to do, so he just walked into the first place that sold alcohol. I spilled as much whiskey as he wanted and watched the Raptors with him. I never saw him again.


#9 Fish Allergy

Back when I served food at one of those super touristy seafood restaurants, I worked a Valentine’s Day double shift. For lunch, this younger couple came in celebrating their one-year anniversary. I offered my congratulations and proceeded to do my usual spiel before taking orders. The girl was looking more and more dismayed the longer I talked. 

Finally, I got to the end and asked if there were any allergies. She looked directly at her boyfriend and stated, “Yes, I’m allergic to fish and shellfish.” Then she looked over at me, very sad. I made sure every aspect of her meal was fine for her. But it was that look of “we’ve been dating a year and he still takes me to a restaurant that could hurt me” that really did it for me.


#10 Last Supper

A guy and his date came in for Valentine's Day. They had a great time, ate a lot of food, and got along really well with my co-worker, who was their server. About two months later, they came back in and requested my co-worker again, who happily said yes to serving them again. So, he then went up and greeted them.

The guy introduced his wife to him, and my co-worker mentioned something about how much he enjoyed serving them on Valentine's Day. They went quiet. The wife got up and left, the guy just lowered his head. Turns out, he had brought his mistress in on Valentine's Day, but my co-worker didn’t realize he was with a different woman this time around, so I didn’t think anything of it. We never saw the guy again.



#11 Nice Dress

I was a server at a popular seafood chain. Well, the night was incredibly busy when a couple came in. They were upset after waiting 45 minutes for a table and they were complaining quite a lot. The woman was decked out in a super nice dress and faux fur coat that was actually very realistic. Well, she was sat at a table and served her frozen drink. She went to lift the glass to her mouth, and inexplicably, the bottom of the cup simply broke and the drink spilled all over her dress and nice coat. It was unfortunate.


#12 Next to You

A younger couple came in for what I can only assume was the first date. They ordered a pizza but never ate. I assumed they were caught up in conversation. The guy must’ve been feeling confident because after about two hours, he got up, went to the bathroom, and then decided to sit next to her in the booth rather than across from her where he was before. I swear to you, she then got up and used the restroom about 10 minutes later. When she came back, she decided it would be best if they didn’t sit next to each other and sat in his original place. Please refrain from doing this.


#13 No Words Needed

I was a waitress many moons ago, and a couple springs to mind. They were an older couple who were dressed nicely. They were polite and cordial to me, but not overly enthusiastic or friendly. They were at the table for a little over an hour and a half, and we didn’t see them say one word to each other during that time. Every time I went over to their table, the atmosphere felt like I’d walked straight into an argument, but they weren’t speaking or looking at each other or anything. It very quickly became awkward.


#14 Don’t Assume

A girl that I used to work with went to lunch on Valentine's Day at an expensive restaurant her boyfriend had gotten a reservation for. It wasn’t hard to see how excited she was. She got really dressed up and was going on to us about how she was so sure that he was going to propose to her. He broke up with her.


#15 Attention, People

Not my table, but back in my Olive Garden days, we had a man who looked to be in his mid-20s tap his empty wine glass with a fork to call for attention of the surrounding strangers. He then got down on one knee with a silver band in hand and asked his girlfriend to “accept this promise ring.” She looked horrified from start to finish.


#16 Out of the Blue

A guy once proposed to his girlfriend and she flat-out told him "no." The guy then threw his arms up and ran out of the building. A little while later, while waiting for someone to pick her up, she talked to us about it. She told us it was completely out of the blue because they'd only been dating for a few months.



#17 Did You Know?

A couple sitting at the bar were enjoying their night out. The man got up from his stool and left for the bathroom. As his girlfriend was alone (and absolutely trashed) at the bar, a random woman approached and revealed that she recently matched with the woman’s boyfriend online and had hooked up a week earlier. 

The girlfriend refused to believe this story, so the woman showed her his profile and their conversation. The boyfriend returned to a sobbing and screaming girlfriend. I felt like I was watching a reality TV show, it was incredible. The poor girl was basically carried out by her boyfriend. It was the most dramatic moment I have ever experienced and it was absolutely none of my business.


#18 Honest Mistake

I was working for a higher-end chain steakhouse in the North West corner of greater Los Angeles. Valentines is obviously one of the busiest days of the year for us, we did about 500 covers between 5:00 and 10:00 p.m. It’s also a restaurant with a very open concept floor plan. There are booths along the four walls of the restaurant and an array of tables in the middle with no partitions or anything between them. 

A younger couple (maybe mid-20’s) dressed to the nines came in shortly after we opened and were seated at a table in the center of the dining room. They were very friendly and pleasant and I could tell that for them, dining at our restaurant was a really special treat. So, I did everything in my power to make it special for them. 

When they were done, probably around 7:00, I brought their check, which was around $300. When I came back to pick it up, the guy had a super embarrassed look on his face and he said he thought he left his wallet in the car. The woman, who was embarrassed for him, didn’t have anything with her because her dress had no pockets and she didn’t bring a purse. 

So, he went out and five minutes later came back in, looking pale as a ghost. He has left his wallet at home and asked if he could call back later with payment information. My general manager wouldn’t let this fly because there’s no collateral of any sort he can leave. So, the guy has to drive home to Burbank to get his wallet while the woman waited.

Now, on the best day with no traffic, it’s at least 40 minutes each way from our restaurant to Burbank. She was there for almost two hours waiting for this guy. We were all so embarrassed for her that the staff kept discreetly slipping her drinks and little amuse-bouche bites from the kitchen. It was one of the most awkward things I’ve ever seen in a restaurant. 

When he finally got back, he was super apologetic to us and to her. He paid the check and tipped about 30%. They then left. It was pretty obvious that it was nothing more than an honest mistake, but I still think about that couple from time to time and wonder how things worked out for them. I hope they’re doing well.


#19 They Don’t Need It

I was a pastry chef at this big resort in Cape Cod. We got a special order from this guy who was coming in for his anniversary on Valentine’s Day. He wanted his dessert to have "Will you marry me?" written on it so he could pop the question when it came out. He called ahead to the front and back kitchen, even came in himself that morning to make sure it was good to go. 

The whole crew was behind him. We had cooks all night coming in the ask if it had happened yet. I wrote the inscription on the plate and dressed it to the nines with gold leaf and expensive chocolate. I was taking a picture of the plate just before it was set to go out and noticed our head waiter come in with a weird look on his face. He said plainly, "They don't need it." She broke up with him before the entrees hit the table.

1024px-אוראל_המאוי_,תיכון_רוטברג,_הצעהWikimedia Commons

#20 Teeth on the Table

One time, this old man proposed to an old woman. He tried to get off the chair to kneel, tripped, fell and I assume broke something since he couldn't get back up. We then had to call an ambulance. My manager had to drive her teeth to the hospital separately because she had taken them out to eat her soup (Lord knows why) and left them on the table in the confusion.


#21 A Big Tip

In college, I waited tables and Valentine’s Day was always a good one in terms of tips. I once saw a couple come in to eat and halfway through the dinner, the man's wife showed up to surprise the couple. The wife took the wine bottle and poured the remnants on the husband’s head. She then took off her ring and told the girlfriend she could have him. He tipped me $100.


#22 Pizza Ring

I worked at a pizza place and the guy asked if I could bake a ring in the pizza. I politely declined. Their waitress did, however, put their ring on the pizza before bringing it to the table. The girl saw the ring, got mad, yelled at him for proposing at a pizza place and walked out. He asked for a box, took the pizza and went after her.



#23 “Classy” Chain

I worked at a chain restaurant that is generally considered "really classy" or "not classy at all" (basically it was a "normal" chain restaurant). We got a few proposals. I always felt bad judging because for some of them, being able to treat a group of people at this place was "making it" in their minds. Other times, we'd get a couple that really seemed like they would normally go to a nicer place, but that restaurant was their first date. No dine and dashers, though.


#24 Ice Cream Sandwich

As a newish waitress, I was helping work a birthday party. Turned out, it was for an acquaintance of mine and knew them fairly well. It was time to bring out their ice cream cake and as I was bringing it out on a tray one-handed, I suddenly tripped and the cake slid forward. Apparently, my body was already prepared to save this cake from imminent destruction and my free hand caught the cake, by the top. So, it was sandwiched between my hands. I was absolutely mortified and nearly in tears. The party told me it was okay, the cake was saved and they just cut the top off. But this event still causes me to lay awake at night.


#25 Different Interpretations

Nothing too scandalous, but I'd say "Happy Valentine's Day" pretty much to any couple that sat at my tables. Occasionally one of them would say something like, "We're not dating." Some of the time, the other person would give a look that pretty much confirmed they both had very different interpretations of what was going on.


#26 Don’t Waste the Chocolate

I had a man and woman sharing dessert. The man playfully put a bit of the ice cream on her nose and she then did the same. Then he did it back once more, but with a different flavour of ice cream. She then flipped out at him because “You know I like chocolate the most. Why would you waste it, you idiot?” In the end, she stormed out because the man couldn’t comprehend how much she was blowing up the situation.


#27 Gone Wrong

My first job as a waitress, a guy wanted to propose to his girlfriend. He came in two months before to book and had everything figured out. He planned to pop the question during dessert. We had champagne, balloons and sparklers prepped for the big moment. The time came, he dropped to one knee and gave a speech about his love for her. 

He then asked her and she said no. She put the ring in her bag, finished her dessert and left. Quite possibly the most awkward thing I have had to witness (alongside around 200 other people.) The manager gave him everything for free. He felt that bad for him. I cringed inside every time I saw that guy after that.


#28 Here’s My Advice

They came in at lunch the day after, so it was pretty empty, but it was still for a Valentine’s Day date. They were both pretty nice at the beginning, the guy asked for a picture and whatnot. As the meal went on, the dude got progressively more partied out and by the time I brought the checkout, the woman was gone. When the dude gave me his card, he said, “I’ll give you a bit of advice. If you’re taking a girl out to break up with her, do it at a McDonald’s and not an expensive restaurant.”


#29 She Ruined It

There was a note in our reservations that it was an engagement. They wanted champagne, a specific seat, and a bunch of other stuff. The server came up to the table with something like, "So, I read we're celebrating an engagement, congratulations." There was confusion from the woman and glaring from the guy. He hadn't proposed yet. She ruined it.


#30 On Second Thought

This couple was meant to be having a proposal dinner. The guy had rung to book a table and had let us know he was going to propose during dessert. He’d given the ring to the kitchen staff so we could bring it out with a cake, and he’d got some balloons and streamers too. He walked in a couple of steps behind his partner — everyone has big grins for them both — but he grits his teeth and shakes his head, surreptitiously dragging his finger across his throat pantomime style. Great. 

Oh, and lucky me, they were seated in my section. It was obvious that she was furious with him about something; she spent the first half of the meal seething quietly and the second having a constant pop at him. While she was in the bathroom, the manager made me double-check he didn’t want us to bring the ring out or anything. “No!” was his response. I felt really bad for him, she really was mean.


#31 Broke Down

I waited on one of the owners of the restaurant I was working at. He was with his girlfriend and her tween kids. He had been dating this woman for a number of months, but it was his first Valentine's Day on a date that wasn't his wife in decades. I don't think he was ready, but he was there to support the business. He broke down crying during dinner and it was heartbreaking. They left early.


#32 Bunch of Roses

I was eating in a fine dining establishment several years ago. In the next booth was a really young guy who had a big bunch of roses on the seat next to him. He kept looking at his watch, looking at the roses, and popping open a ring box for a peek at the ring. He did this for a half-hour or so, then began calling and texting someone over and over. As we were waiting for our check, he handed my wife the roses, mumbled something, and walked out.


#33 All at Once

I had a section one Valentine’s Day that had a marriage proposal, a 40th anniversary, and a break up all at the same time. The break up was the worst. The guy brought his high-class date a gift; a mini ceramic bear holding balloons. He presented it when I was at the table and she looked at it like it was something disgusting. I just knew this wasn’t going to end well. She left at the end of the meal and must have said something because he stayed at the table for another 40 minutes, head down and crying. I felt bad because he saw the celebrations going on at the other tables.


#34 Golf Ball Celebration

My first day of work on the floor at a country club was the weekend after Valentine’s Day. There was a lot of buzz in the back about this adorable family, where every year the mom brought the son out to a nice dinner at the club and the father brought the daughter to the men’s section for dinner. It was their Valentine’s Day tradition. The kids were both 14 or 15.

I’d also been filled in on the gossip that the waitress I replaced had left to have a baby. She was really young and there was blanket disapproval from the staff and a lot of the members. I was serving the mom and son in the more upscale dining room, but getting drinks where the dad and daughter were, so I was around both groups.

I was bringing a bottle of wine to the mom when a woman walked in with a baby and started handing personalized golf balls out to people as a birth announcement sort of thing. She handed one to the mom at the table and one to the son and walked off. Suddenly, the mom knocked her glass to the floor and started whisper-shouting at the son.

People were congratulating the new mom and pretending to be friendly. Then each table seemed to go perfectly quiet one after another. I went to the bar to get a new glass and saw a man duck over to the dad’s table and say something to him. The man got up without saying a word, (even to his daughter) and dashed into the men’s locker room, leaving her sitting at the table.

The whole room went quiet. Nobody intervened as the old waitress went over to the table, handed the girl a golf ball, said a few words and walked out of the club. The girl started sobbing. Eventually, the mom seemed to have remembered the daughter, because the brother came and led her out, and they all left together. When I was clearing the table, I read the golf ball, which said: Waitress +Member (dad) present. Baby first name and member’s last name. And the date.


#35 Eating His Feelings

I was working at a corporate sports joint that specialized in chicken wings. Valentine’s Day was insanely busy! As the evening wound down, someone called in saying they were a professional food critic and demanded to speak to the manager. After a 15-minute call, the manager told us the "critic" rated us a B- and said the food was good, but the service sucked. 

He said he would leave that last part out of his review if we comped his meal and gave him vouchers for free meals in the future. But, he refused over and over to say where he worked. Confused, the manager talked to the server who confirmed that the guy ate alone, ran her around while shamelessly hitting on her, and left zero tip. This idiot wanted free food because the server didn't call him immediately for a date.


#36 Where to Find Him

I used to work the front desk at a hotel. One Valentine’s Day, I was working the night shift and this woman came down looking like she just went a few rounds in a boxing ring. The woman started sobbing and asked us to call the authorities, which we do immediately. Turns out, this girl and her boyfriend got into a fight. From what I could tell, this probably wasn’t the first time.

After the cops showed up and hauled the dude off, my manager offered her a different room. She accepted and I went up with the woman to help her collect her stuff and move to the new room. There were a bunch of bottles in the room and she donated them to the front desk staff.  The cherry on top of everything was that the dude’s wife called later that night saying someone had stolen his card as he was out of town on a business trip. I told her where she could find her husband. 


#37 Sushi to Go

I worked at this Japanese restaurant and had one guy come and order a bunch of sushi to go. He said that he was going to surprise his girlfriend. He came back 30 minutes later and asked us if he could return some of the sushi. Apparently, his girlfriend has a seafood allergy and couldn't eat anything he ordered and she was mad he spent so much money. So, she made him come and try to get some of it back. Obviously, we couldn't really give him a refund on the food, but we made him a chicken hibachi on the house so he could have something to take back to her. We felt bad for the guy.


#38 That’s True Love

I was working backline at a fast food place on Valentine's Day. It was 8:00 p.m. and the store was empty. One couple came in and ordered their food. I just finished making it when I saw the guy get down on his knee and propose with a packet of horsey sauce. She said yes. I told my manager and gave them a free cookie because accepting a proposal done by condiments in a fast food joint is true love.


#39 Through the Kitchen

A man from my table went to the restroom and was gone for a while. As I was passing by the restroom, he ushered me to the side and hurriedly whispered that he needed to leave through the kitchen because his wife’s best friend was sitting near him and his date. Of course, as I learned then and there, the date was not his wife. We boxed the remaining courses up and did a walk of shame through the kitchen. He was angry, she was crying, all while the rest of us were stifling our laughter. He ended up tipping well on the prix-fixe, which was nice.


#40 Surprise for Everyone

I was working as a duty manager and one of the tills kept dropping off the network. As I was trying to fix it, I could clearly hear the conversation of the table by the waiters’ station. It started out sweet enough with her excitedly telling him she was pregnant. He went quiet and didn't say anything for a bit and then asked her what the plan was. 

She said she was keeping the baby. He said he didn't want kids and had told her this. She got upset and said she thought he'd be happy and change his mind when he found out. Turns out, she stopped taking the pill without telling him, thinking she could turn him around. He said he knew she could be a little nuts sometimes, but this was next level. 

He told her it was over and she could send someone to collect her things as he wanted nothing more to do with her. He called me over to pay the bill and just left. The guy never even shouted, he just calmly dismissed her and noped out of there. I couldn't even look her in the eye, just left her to leave in her own time.


#41 Replacement Date

These two were on a date and the guy went to go use the bathroom. The girl just up and left after he went to the restroom. When the guy came back, he sat around for a while until asking his waitress where she went. She replied that she left. The guy then asked the waitress if she would go on a date with him. The waitress said no.


#42 Blowing a Tire

I blew my car’s tire and my friend came in to bail me out. We’re both straight dudes and forgot it was Valentine’s Day. We decided to have dinner and were both coming from an important meeting, so we had suits on. We didn’t catch on until the end on how the entire wait staff thought we were just the cutest gay couple.


#43 Cleaning the Mess

I served at a Japanese hibachi restaurant back in the day.  I once had this one couple come and the dude dumped her after they were done eating. She then got up and threw up a trail of food. It was probably a good 20 feet as she ran to the bathroom. The dude then got up and left the girl. I was left to clean the mess.


#44 Nervous Date

I used to be a waiter in a five-star restaurant. It was my first week. One guy was about to propose and it was obvious by how much he was sweating. He was drenched, but I tried to make them both relax. They went on to finish up their meal. As soon as the cake arrived, he went on one knee and she stood up suddenly. But, he wound up hurling right on her high heels. After the shock of what just happened, she still ended up saying yes.

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#45 Get Over It Already

I used to be a barista and this one guy on Valentine's Day came in and asked us to write "will you marry me?" on a cup. It didn’t go well. She looked at the cup while he went down on one knee. She said nothing, put the cup back down and just walked away while shaking her head. He, on the other hand, got angry and started to rant about how she should have gotten over him sleeping with her sister already. We had to ask him to leave.


#46 Fruit Bouquets

I was a delivery driver for a fruit bouquet company and I had two arrangements from the same guy. Routes were made for me and the truck was loaded so there was no way I could mess this up. I delivered both arrangements to the appropriate address. I headed back to the store to find the store owner and the guy who sent these in an argument. 

This idiot put the wrong name on each delivery, sending them to the wrong house. The names were on the card with the arrangement… along with the phone numbers. So, both women called each other and then called the guy. He tried to say it was my fault. Then, the person who took the order. He ordered it online . All we did was import the order. 

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#47 A Wild Ride

It was my first week serving and I was trying to do everything by the books. This normal-seeming couple was satisfied throughout the meal. I asked if the check would be together or separate, which was a big mistake. I figured it would be together and went to the gentleman, but not wanting to assume, I asked. They said together, and I went to get the check and drop it off. 

I came back and she was writing a paragraph about how I shouldn't have asked. I grabbed my manager and she stopped by the table only for the crazy lady to complain. They left, the gentleman tipped me well and seemed embarrassed at the situation. The crazy lady filled out our survey, complaining and called the store three times after to complain. I brushed it off because she obviously had insecurity issues but what a wild ride.


#48 He’s Not My Boyfriend

I was hosting at a really busy brunch place and Valentine's Day was one of our busiest days. We had a full waitlist with tons of people in the lobby when this dude walked in with this huge teddy bear and a bouquet of roses. He said he wanted to drop them off for my co-worker, so I let her know he was there. But, understandably, she was running around so it took a bit. While waiting, a bunch of folks waiting for tables complimented him on how sweet he was to do that for his girlfriend and how jealous they were. It was kind of cute.

When my co-worker finally was able to come up front, there was a lot of gushing from the people. Again, we were slammed, so she ran back after taking the items and it was back to work for all of us. When it cooled down, I asked her how long she was dating her boyfriend. She replied, "He's not my boyfriend. He was the salesman where I just bought my car and I think he got my workplace from the paperwork." That was pretty disturbing.


#49 Ceiling Water

I was the chef at a pretty fancy place. We did a four-course tasting prix fixe and were always booked to the brim for Valentine’s Day. The owner was out of town and the place was packed during our first seating. The pipes to the apartment above the restaurant suddenly burst. Nasty, cold water rained on everyone and everything. The fire department came. The owner said to give everyone champagne, clean the place up and keep going. As if anyone wanted to continue their meal soaked through on a cold night in ceiling water.

Ceiling_sheetrock_damaged_by_water_so_paint_was_peelingWikimedia Commons

#50 Rest of the Meal

I was waiting on a couple in their early 40's on Valentine’s Day in an Irish pub. The dude was head to ankles in camo clothing and rude. She was decently dressed for a date and very pleasant. She thanked me for working on Valentine’s Day and said I probably have someone I'd rather be with. Then he said, "Pfff! She's too skinny, who would want her?!" I only spoke to her for the rest of the meal.

Mad_Murphys_Irish_pub_of_Tallinn_(8128231195)Wikimedia Commons



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