48 Waiters Share The Most Cringeworthy Dates Theyve Ever Witnessed

1. Death By Hot Sauce

I worked in a restaurant that had a huge selection (150+)of hot sauces. We sold them by the bottle but customers could sample any of them and use them on their food. A couple came in, the guy started bragging about how much he loved hot sauce and how he never found one that was too hot. He asked for the hottest one we have. I brought the bottle to his table, he filled a spoon with the sauce and made a big production of how he was going to eat it. I told him not to, the hostess told him not to, the waitress serving the next table told him not to… he put it in his mouth, started choking and gagging, puked on the table then passed out and did a faceplant right into the puke!! We called 911. He woke up right away and kept gagging for a while. He refused treatment when the paramedics showed up. They left without even ordering a meal! The girl told one of the restaurant staff that it was their first date.

2. Unwelcome News

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

3. Calling Mommy

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

4. The Dine And Dasher

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

5. A Failed Proposal

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

6. Random Violence

One Summer I worked at Cheddar’s. A couple in probably their late 40s walked in and sat at one of the high top tables in the bar area. The man ordered a shot of whiskey and a beer, the woman a diet coke. When the drinks come he takes the shot, takes a pull on his beer, and backhands his SO so hard she fell out of her chair. He just sat there calmly drinking his beer until his arresting officer arrived.

7. He Ordered For Her

Couple sits down at my table. Do the usual greeting. Ask them if they would like to start out with a beverage. The female replies, “coke, please”. The male stops her, interrupting “uh, make that a diet coke. I’ll take a jack and coke”. The date didn’t get any better.

8. The One Night Stand

The worst I’ve served by far. I worked at a breakfast place so we got a lot of one night stands awkwardly making small talk, but that was mostly just funny. I became really good at figuring out how far into a relationship a couple was. Anyway, this pair. They came in and sat themselves (we had a host) and then the dude asked to switch tables. You chose that one, though! Anyway, he orders the drinks. One water with extra lemon for the gentleman, two small orange juices for the lady, even though I explained it would be cheaper to get a large, but he declined. When I went back, he asked for more sugar and lemons. He had used all twelve-fifteen packets of sugar (and sweet n low, and cane sugar, and equal) in his water with extra lemon. Their food order was insane. Every ticket I took at that place usually cost about $5-10 per person, and this guy’s ticket was at around $30. His girlfriend’s was $8, including the OJs. Time comes to pay and he stares at the girlfriend. She pulls out a card, which comes back declined. She starts crying when he says he doesn’t have money. She goes outside, calls her mom, calls her bank, whoever. She’s screaming on the phone for about twenty minutes. While she’s melting down outside, dude comes up to the register and throws down a wad of ones. “Here.” And leaves.

9.The Nervous And Sweaty Guy

First date for a couple in their late 20’s. Started smoothly, the obvious first date jitters and awkwardness but nothing odd.

Ten minutes later they order and the guy is sweating bullets, really nervous.I checked on them about 5 minutes later and he’s looking distinctly off.

He didn’t make it to 20 minutes. He shat himself and ran out leaving the girl sitting there in shock and pretty upset.

The story was she had been set up on the date by a friend, who’d told her that he was nice, but extremely shy and nervous. Apparently it was all good until he needed to talk about himself, then shit city occurred. That chair went straight to the dumpster.

10. No Way To Ignore This

A couple in their late 20s was having a quiet discussion in their booth and were going from their table over to the bar to use the phone and back to their table. Then suddenly the woman yells “YOU BROUGHT A HOOKER INTO MY MOTHER’s HOUSE YOU COCKSUCKER” and storms out.

Restaurant is dead silent, and me and the bar tender just look at each other and burst out laughing and the guy shuffles back to his table.

11. The Showoff

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

0

12.They Said I Looked Like Their Daughter

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

1

13. Awkward

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

2

14. She Flirted With The Waiter The Whole Time

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

3

15. She Sprinted Out Of There

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

4

16. “Call Me Daddy”

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

5

17. Paid For Her Silence

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

6

18. The “Fucking Disgrace”

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

7

19. The Honeymooners

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

8

20. “I Don’t Like To Share”

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

9

21. “Never Ever Get Married”

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

0

22. The Cheapest CoupleTo Ever Live

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

1

23. This Is So Sad

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

2

24. The Magician

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

3

25. Ok, This One Is Also Just Super Sad

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

4

26. Not A Great Way To Remind Someone Who You Are

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

5

27. WTH?! How?

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

6

28. The“Bitch” Who Liked Assholes

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

7

29. A Bad Break Up

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

8

30. Holy Crap

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

9

31. Ditched

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

0

32. The Overprotective Father

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

1

33. Typical Blind Date

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

2

34. The Things You Hear

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

3

35. The Bird Savior

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

4

36. There Was Blood Everywhere

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

5

37. “Changed My Perspective”

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

6

38.*Cringe*, Another Proposal

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

7

39. The Freaky Couple

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

8

40. The Slutty Army Wife

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

9

41.Her Reaction Was On Point

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

0

42. Oops!

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

1

43. Completely Clueless

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

2

44. Manager Is A Saint

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

3

45.The Champagne Volcano

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

4

46. The Instagram Addict

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

5

47. What Part Of The Cow Are Pork Chops From?

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

6

48. So Dark Not Even Light Can Escape It

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

7

Read more: http://thoughtcatalog.com/eric-redding/2016/01/waiters-share-the-most-train-wreck-cringeworthy-dates-theyve-ever-witnessed/


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