Servers Share The Most Cringeworthy Dates They’ve Ever Witnessed

November 18, 2018 | Christine Tran

Servers Share The Most Cringeworthy Dates They’ve Ever Witnessed

Bad dates just aren’t awkward for would-be lovers. They’re also horribly awkward for the poor souls with the misfortune to serve drinks, take orders, and generally keep their “happy face” on even as things fall to pieces. We’re speaking, of course, about loyal restaurant servers. Reddit asked food service workers of the Internet to share the most awkward dates they’ve ever had the misfortune (or pleasure) of seeing on the job. The main takeaway? The human race should stop proposing at restaurants unless we’re 100% sure the significant other will say yes.

Split the bill for these 42 delicious stories about the most awkward dates ever seen by servers.

42. That’s Not What We Mean by Get a Room

I work at a Japanese restaurant, and one couple comes to mind. It was the "worst" for everyone else involved. We offered "private" rooms that have sliding doors, and this couple clearly was hitting it off very well... to the point that after a few drinks, she had moved to his side of the table and they just went at each other's faces & bodies for about two hours.

They could have done all that with the doors closed and it would have been less cringey—still cringey nonetheless—but no, the sliding doors were wide open for all the patrons to see. Kids, big groups of people, waitstaff, runners, etc...

If I remember correctly, they tipped pretty bad too, so it was not a fun time.

Cringeworthy Dates factsGetty Images

41. No Points for Trying Too Hard

This is actually a story where the (somewhat awkward) guy was doing pretty good until my boss screwed it up for him.

So there was this couple on a first date, seated at a table in the back. At first, I didn't think much of it, wasn't even aware that it was a first date until the restaurant's phone rang. A man called to let me know his son was there on his very first date ever (the son was in his late 20s). Obviously, this was a big deal to him and he called the restaurant to make sure we would do our best to make sure they have a pleasant evening.

My boss heard and instantly went to the kitchen in order to make sure they would get a "special treatment." What followed was plates with rose petals, red hearts etc. etc. Way over the top. When serving the plates, my boss even mentioned the phone call. To finish it off, the desert came complete with fireworks and all that.

The idea was sweet, but obviously this was way too much for a first date of two people who were basically just getting to know each other. As the evening progressed, the girl was visually put off by my boss trying too hard. Poor guy. Up until then he had been doing quite well, the pair seemed to have a lovely evening. Until my try-hard boss entered the scene that is.

The girl was polite toward the end of their date, but it was obvious there was not going to be a second date. And it wasn't even the guy's fault, other people ruined it for him. I felt so sorry for that dude...

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40. Let’s Split the Check and Literally Everything Else

I guess you could call this a couple date. I was working at a wine bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered.

Once appetizers came out, the man thought it would be a good idea to serve his wife divorce papers.

I did my best to avoid that side of the bar. I did bring out tissues for the wife, who was breaking down. I ended up boxing up the dinner. The guy paid, but I do not envy that ride home.

Cringeworthy DatesFlickr

39. Heartbreak in Any Language

Served a deaf couple having a fight. They went from both of them signing furiously to her crying and signaling to me for a stack of napkins for, I assumed, her tears.

She whips out a pen and starts writing paragraph after paragraph angrily. It was awkward because I kept having to come back to the table since they ordered multiple courses. He was just eating and signing while she was hunched over the table writing away while crying. When they finally left, they tipped me pretty well, so I guess it wasn’t too bad?

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38. Never Leave Without a Back-Up Beau

Working at a Chili’s on Valentine’s Day. The girl gave me her number with her boyfriend in the bathroom. I came back and had to deal with her being sweet to him and nice the rest of the dinner. I did not call or text her; just felt weird every time she’d look me in the eyes.

Cringeworthy Dates factsShutterstock

37. Dine, Dump, and Dash

Was a cocktail waitress at a bar in a high-end restaurant a couple years ago. This couple comes in right around peak hours; guy looks annoyed, girl looks really excited. The whole time, the girl is trying to talk to this guy and he's completely ignoring her. He gets a call and talks on the phone for a good ten minutes, hangs up and starts talking to anyone around him but her.

He's getting more and more drunk and starts hitting on the female bartender and eventually the cocktail waitresses (myself included), telling us he could get us all much better jobs in Atlanta. The girl he's on a date with has started crying at this point, and once he actually notices, he yells at the bartender because it was obviously the restaurant's fault that she was upset. She yells at him to stop yelling at the bartender because he's been such an awful date and he goes off, tells her he didn't even want to eat here, she should've picked a better place, and he isn't paying for her food and drinks.

He then tells her that she didn't look fat in her picture. He wouldn't have asked her out if he'd known she was that big (probably met online kind of thing). She retreats to the bathroom and the guy continues to make a scene. Another girl at the bar and I go to check on her while the bartenders and manager try to deal with him.

The girl is super upset and I tell her there's a back door she can leave through and I can get her tab from the bartender. I go back out and the guy had already stormed out and refused to pay, leaving his date with a nearly $200 check. She didn't have the money to pay, so a couple of the bar regulars covered it. Made the whole night super awkward and stressful. Definitely one of the more memorable experiences of that place.

Cringeworthy Dates factsShutterstock

36. Separation With a Side Dish?

I don’t know if this counts, but when I was a waitress at Olive Garden, one of my tables was going over their divorce paperwork. When I greeted the table, I asked how everyone was and the woman said, “Terrible! We are getting a divorce.” Like what do I say to that?

Cringeworthy Dates factsGetty Images

35. Eating Your Match

Really little guy, maybe 5 foot 4 and 120 pounds, comes in with a gigantic woman, probably 6 feet tall and easily 300 pounds. Both tatted the heck up with piercings to match.

The woman orders her dish, and before I get the guy's order, he says in a sexy voice, "I think you want more than that." She smirks at him, says, "You know I do," and orders three more entrees. This was clearly a thing for them. They seemed incredibly happy together and became regulars at my restaurant.

I feel like I played a not-insignificant role in this bizarre couple's eating fetish for like three years.

Cringeworthy Dates factsPexels

34. Keeping It on This Side of the Family

There was a couple at my work having drinks. Girl went to the toilet, came back, and admitted that she’d been sleeping with the guy’s brother. Apparently, glasses were thrown across the room and they both got kicked out.

Cringeworthy Dates factsMax Pixel

33. Gruesome Twosome

This wasn’t so much as awkward but just unusual: I served a young couple at a high-end Italian restaurant who came in wearing matching outfits. I asked them what the occasion was. They were celebrating their three-month anniversary. I’m so glad they found each other.

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32. The Terrible Trio

A girl brought two tinder dates and played them off each other game-show style. They seemed to be unaware this was what would happen. Splitting the bill was hilarious.

Cringeworthy Dates factsMax Pixel

31. A Special Guest Appearance From…

I had a mid-40s man with a young and attractive mid-20s woman sitting at the bar. They were engaging in small talk and ordering drinks, nothing out of the ordinary. After possibly 45 minutes, a lady storms into the bar and immediately goes up to them.

She grabs the man by the shoulder and says, "You…You're a [c-word]" and walks out. The man turned to his perceived date and says, "Yeah, she does that," and then left the room, leaving his date to sit there, staring blankly into oblivion until she left. Odd.

Cringeworthy Dates factsGetty Images

30. A Table (and House) Divided

Not exactly a date—but I served a couple one time who had met up to discuss the terms of their divorce at the fancy-ish restaurant where I worked at the time. They came before the dinner rush so they were pretty much my only table, and every time I’d check in on them, the wife was extremely angry/tearful and they were bickering about holiday schedules for their daughter/timeshares etc.

It wasn’t the end of the world, but it was extremely awkward to butt in to change out their forks or refill drinks while they were so emotionally charged.

29. Exit, Pursued by a Ditched Date

There was a couple sitting at the bar together. It seemed like it was a first date. Maybe after 30 minutes of them being together, I’m in the back, rolling silverware, and the dude comes running into the back and goes, “There’s an exit back here, right?” and proceeds to bolt out of the back door.

We were all flummoxed. The girl sat at the bar alone for at least another 45 minutes before she left.

Cringeworthy Dates factsMax Pixel

28. Not So Happily Ever After

Straight up someone proposed last year during Xmas service. Everyone's clapping and cheering the guy on, she says yes obviously, the night continues. When they were leaving, I see her give the ring back to him, slap him, and jump in a taxi without him.

Dude just sparked up a smoke and walked away. To this day I have no idea what happened.

Cringeworthy Dates factsGetty Images

27. Lean in, Lean out, Get out

They sat down, and from the girl's body language, you could tell she was into him. As the date progressed, she closed off, then sat pretty much sideways, then was playing on her phone. The body language shift occurred over maybe 1.5 hours. He didn't stop talking the entire time.

She did give some nods and "uh huh"s in response; even perked up a few times to contribute. But his monologue never stopped.

Cringeworthy Dates factsPixabay

26. The Fall of an Empire

Bartending a day shift at an upscale Italian place in a high-end shopping centre over the Christmas season. Couple comes in, starts drinking, and are VERY flirty with each other. They clearly liked the attention. I wasn’t quite sure why the man seemed familiar, but he had a face I knew from somewhere.

Midway through their lunch, the woman used his name, and it dawned on me that the man was the husband of my previous boss. I told him he looked familiar and asked if he was “Mark” from “That Restaurant on the way to the Beach?”

He said that he was not. But the woman he was with insistent on making it awkward and peppered me with questions like, “I’ve heard the owner of that place is crazy, did you know her?” She was backhandedly trash-talking “Mark’s” wife and the whole thing was so uncomfortable. He was an all-around bad dude though and deserved it.

For additional context, his family had owned “That Restaurant on the way to the Beach” and his wife (my former boss) ran the place until she caught him cheating. They divorced, she got the restaurant and continued to run it with her sister.

Fast forward a few years, and the two eventually remarry. It was during their second marriage that he turned up at my bar with his mistress.

Cringeworthy Dates factsMax Pixel

25. Don’t Get Cheesy on Me

Husband and wife fight. Wife cried. Husband got up and threw a pizza slice at her face.

Cringeworthy Dates factsShutterstock

24. If at First You Don’t Succeed, Try Again and Again

I was at one of these fancy speakeasy-type bars they've started opening up installing a new invoice printer for their PoS system. Waiting for the printer firmware and driver to install can take 30 or 40 minutes on slower computers, so I'm people-watching.

As I'm standing there watching bars fill up, I notice a gorgeous blonde in her late 20s is sitting with a very well-manicured looking guy in his mid-40s. He's dressed like he just left a high dollar law firm, and she looks like she's going to a fancy professional cocktail party after their date. He is polite, talkative, and super into her, but you can tell that she isn't reciprocating the feelings. To be honest, by the look on her face, she's anywhere but in that bar at the moment.

The guy goes to the bathroom and she quickly picks up her phone and frantically calls someone and begs for pickup ASAP. The gist of the call was the guy was her mother's co-worker and her mother had set the date up, and our girl really wasn't feeling it. About 15 minutes later, a guy around her age comes in, throws some cash on the table and excuses them. She cites some vague emergency and is escorted out.

The older guy continues drinking ($140 tab, note that I'm standing at their main cash register) and starts flirting with the waitress, fails to get her number, pays in exact change without tipping, and leaves.

Cringeworthy Dates factsPexels

23. First-Class Rejection at Bargain Prices

A guy proposed to his girlfriend at the booth across from my friends and me... at Olive Garden. When he got down on one knee and opened the box, she was shaking her head and then just stared silently. It must've been a whole 30 seconds of pure silence, but it felt like an eternity. Then, the guy proceeded to describe the ring, how much it cost, the different aspects of it, etc. Finally, the girl just went, "Nooooooo" and the guy just sat back down, and they tried to finish their dinner. I caught eyes with our server and he made the most perfect "holy hell that was bad" face. Geez that was awkward.

I still picture him saying, "My love for you is like these breadsticks... Unlimited<3" He didn't say it, but I still picture it.

I really don't think she rejected him because of the location. Obviously, I can't be certain, but she seemed like a nice girl and had this "What're you doing? You hardly even know me" expression on her face.

Cringeworthy Dates factsGetty Images

22. The First Word and the Last One

There's a habit of some older couples where the elderly gentleman will order on behalf of his wife. I guess it might have been cute and romantic once, but it doesn't work with some younger couples.

I was serving a younger couple (early 20s), who seemed pretty early into the relationship. They were ordering drinks, and he orders her drink for her. Far from being dazzled by him knowing what she wanted, she didn't want any of it.

"Well I'd actually like a latte, not a coke. But fine whatever, if I don't get a say..."

He responded quite angrily with "Oh sorry, have what you want then!"

She got her latte and he glared at me. They ate and left. Not been in since; I'm sure they're doing well.

Cringeworthy Dates factsMax Pixel

21. Five-Ring Circus

I worked in a resort hotel, high end, I waited tables in the fine dining restaurant. It was pretty common for people to propose there, so much so that I had a system for the whole thing.

One guy came in and wanted to do the ring in the champagne thing, and I talked him into doing a dessert alternative that doesn't result in a sticky ring and champagne on the floor. Anyway, long story short. I bring the ring, she says, "Darnit, I've told you before I'm not marrying you."

He flips, she's super calm about it and basically treats him like a child having a tantrum, which to his credit he was not screaming or anything, just very upset. He left, she ate the dessert, eventually, he came back and paid, and they left together. Super awkward.

Cringeworthy Dates factsShutterstock

20. Cupid Goes to Daycare

I was serving a couple probably in their mid-20s. It was Valentine’s Day and they were arguing a lot (probably because it was a chicken wing place and Valentine’s Day).

The guy ended up calling me over to the table to calmly ask me, in front of his date, “Do you have a high chair or a booster seat since someone wants to act like a darn child?”

I was speechless, she wasn’t. They left soon after that.

Cringeworthy Dates factsGetty Images

19. Too Young to Talk?

Saw a really young couple, likely 13 or 14, come in and not say anything to each other. Neither could look each other in the eye, they were so shy. They ordered their food barely above a whisper.

Occasional cringe faces were made at the food they were staring at. They were having a very awkward time and it was painful for them as well as me.

Cringeworthy Dates factsGetty Images

18. Overtime Means Double-Time…

I used to work the bar at a restaurant that was walking distance from a very rich neighborhood. One of my regulars was an NFL player who would bring his fiancé in a couple times a month.

One day, the fiancé came in alone and already very drunk. She sat on her usual barstool and started rapid-fire typing on her phone without ordering anything. I kept my mouth shut because she was already wasted, and she usually tipped me very well.

I turned my back to type in someone else’s order, and I heard someone yell and then the sound of breaking glass. Turns out Mr. NFL player had walked into the restaurant with another woman. The fiancé had picked up someone else’s drink and threw it at his head.

Cringeworthy Dates factsMax Pixel

17. Relish the Youth

I witnessed another waitress accidentally drop a very small (and plastic, like a plastic cup) container of coleslaw on a baby's head, coleslaw side down. The mom was LIVID, but the dad was laughing his butt off, which made the mom even more mad. The poor waitress had no idea what to do besides get some paper towels for them.

Cringeworthy Dates factsMax Pixel

16. Duty Calls for Everyone

My boss told me he had to serve his ex-girlfriend and the guy she cheated on him with...

Cringeworthy Dates factsGetty Images

15. No Room for Improvement

Had a couple come in. Guy is telling woman about some real estate investment opportunities he has coming up (for himself). She tries to tell him she doesn’t think it’s a good idea, and he responds with, “No one asked for your opinion, you don’t know what you’re talking about.”

She sat in silence for the rest of their meal, looking at her phone. When he goes up to pay, and I go clear some of their dishes away, she tells me it’s only their second date, and she doesn’t think she’s going to see him again. Couldn’t bring myself to respond with anything other than, “Please don’t.”

Cringeworthy Dates factsPxHere

14. A Fiery One

No joke, I had a woman bring in a candle and put it on the table. Not a little candle but a big, giant one. I told the woman her and her date could NOT have that on the table. She literally said, "Y'all tryna get hit?"

This was in a mall in a pretty big town at a chain restaurant. I just couldn't believe it. Thank God managers exist.

Cringeworthy Dates factsPxHere

13. This Relationship Won’t Hold Water

This woman arrived before her date and was sitting alone in the booth waiting. She had a kind of generally angry air about her. This woman was enormous, and the hostess had seated her at one of our smallest booths. Her stomach was fighting the edge of the table.

She ordered a glass of wine and sat there drinking it. By the time the guy arrived, she had finished it. I asked her if she'd like another glass, and she said with a scowl on her face, "I don't know. It depends on whether or not he's paying." The guy looked kind of embarrassed and said sheepishly, "Uh, yeah I'm paying..."

I wanted to tell him to run far away.

Cringeworthy Dates factsPexels

12. You Can’t Bank on Love

Mid-20s-aged couple on a date. First date I think but I'm not sure. It seems a bit awkward but they make small talk throughout dinner. When it's time to pay, the guy asks for separate checks. Girl looks surprised. He pulls out his card, pays, and then goes to the washroom.

I run the girl’s card (she already looks nervous) and it gets declined. We try again, it is declined again. I ask her if she needs a moment to figure it out (check her online banking or whatever) and she says yes. Guy comes back. She runs her card again (declined) and he sits stone-faced while she is getting more and more anxious.

I walk away again, and when I come back the guy ends up paying for it. He wasn't thrilled. It was super awkward for all of us, but I cringed so hard when it was obvious that she had just EXPECTED him to pay for her.

Cringeworthy Dates factsGetty Images

11. You Can’t Charge That to Overtime

I worked at a Subway a long time ago. My regular doctor came in with one of the medical assistants (not his wife). They were sitting side by side and she kept rubbing his leg.

Dude, you're a doctor. Use that brain of yours. If you are going to be a jerk and cheat on your wife, at least go on dates in another town where people won't recognize you.

Cringeworthy Dates factsPublic Domain Pictures

10. Playboy Pays Well

I definitely have seen a lot of awkward last dates.

I used to work at a very small neighborhood restaurant. Everyone who came in was a regular. Most were couples in their 40s-50s out for a quiet dinner, but there was one stand-out.

A VERY handsome man in his early 30s would come in, it seems, only to break up with women. About twice a month, he would come in with a beautiful woman, and partway through their meal she would be crying. I always tried to clean the tables near them for as long as possible, but I never heard much of his speech.

He always tipped well and was super nice to me and my coworkers, it was just brutal seeing him bring in a new lady and knowing what she was about to go through.

Cringeworthy Dates factsGetty Images

9. Love Bites

I work in an Italian restaurant. A few years ago, I waited on a guy and girl who met for the first time upon arriving at the restaurant. There were awkward pleasantries exchanged at the door and then they were seated.

When I was taking their order, the guy asked if we had soup because he had mouth surgery a few days prior and chewing food was still a little rough. We don't have soup, so I explained that the "softest" food on the menu was gnocchi. He ordered the house gnocchi and proceeded to cut each tiny dumpling into four or more pieces and slowly chew each piece. He ate that entire dish over a three-hour period and the girl stuck it out for the whole thing. She looked miserable and I'm pretty sure they never saw each other again.

Cringeworthy Dates factsPixabay

8. One for Two Dining

Dude would not stop eating her freaking food. Other table actually noticed, and we casually "people watched" the date together. Girl looked miserable. We asked if she wanted the rest of her food boxed up. She said no, but the guy was like actually, yes. It was painful.

Cringeworthy Dates factsPixabay

7. At Least He’s Moving on

Served a couple a few months ago. Every time I walked over, he would always be the one talking, and she would just be sitting there not having a good time. At the end, I asked if it was one bill or separate and she immediately piped up, "SEPARATE."

I go and take his payment, and as I hand over the debit machine to the girl, I see the guy take his phone out and start swiping through Tinder.

Cringeworthy Dates factsGetty Images

6. What’s Your Number?

Had an obvious first date where the lady was grilling the guy on how much money he makes. He didn't really want to answer. It was awkward serving steak and salad during an interrogation.

Cringeworthy Dates factsGetty Images

5. Dinner With a No Hit Wonder

I work at a dinner theater. We usually do proposals where we set up a "random draw" where the "winner" comes up on the stage to win their prize and are then surprised by their partner, who proposes. It's usually sweet and makes everybody in the room all fuzzy and warm.

This one guy wanted to take it further, and requested to perform a song—he brought his own music and everything. We're pretty easy-going at this job, so we agree to let him do it.

We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently, this guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy that seemed to focus on how he was sorry for cheating on this woman with her sister, and at the end of it, he gets down on one knee and proposes.

Usually this gets a round of applause, encouraging the person to say yes, but not after that train wreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says, "No, what's wrong with you?" She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is, "Well, that's that."

The guy ended up staying for the rest of the show and had many more drinks. That was years ago, and it still remains one of the cringiest things I've ever seen.

Cringeworthy DatesPixabay

4. Let’s Pay to Play Pretend

One of my first jobs in New York was managing a lounge/cocktail bar in a high-end hotel. At around 3 or 4 o'clock, a guy who looked pretty cheesy (slicked back hair, bad suit, etc.) came up to me and demanded that he get that window table tonight for his date (he had a reservation for 8pm). I explained to him that I can’t guarantee it etc. etc. and he slipped me $400 with the “How about now” look in which I eventually caved in and told him that I’d take care of it.

He then pulled another stack of hundreds and started counting them in front of me while asking if I could go a little extra by coming over to the table when he was there with the date and pretend that I knew him from a movie. At this point, if I’ve gone this far, why not?

Sure enough, he rolled around later in the evening with a blonde bimbo, and after they’d had a glass of champagne, I approached the tables around them and checked on how they were doing before going over to him and did the whole “How are you enjoying your evening?”

And before walking off, I did an Oscar-worthy double take with an “Are.. are you... by any chance..? You must be..” at which point he had this douchey smile lapping up the “recognition” he was getting from this young dude he’d just paid off. Most importantly for him though, it worked—she was loving it—and they left shortly after, and he slipped me another $600 on the way out.

Cringeworthy Dates factsFlickr

3. Tapped the Glass Too Soon

When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person to date.

Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stands up, taps his wine glass to get everyone's attention, and then proceeds to tell EVERYONE what a fantastic person his girlfriend is, how much he loves her, and how lucky he is to have her in his life.

The whole time this is happening, she is just sitting there watching him with the most boring look on her face. It was so weird. Kind of like, "Yeah, tell me something I don't know."

Then the poor guy pulls out a ring, gets on one knee, and asks her to marry him. She gives him the most disgusted look imaginable and says, "THIS is the ring you expect me to say yes to? Are you stupid? Could you be any cheaper?" Then she gets up and walks out, leaving the poor guy just kneeling there.

I didn't charge him for the meal.

Cringeworthy Dates factsGetty Images

2. I Think This Counts as an Emergency Worth Escaping

Late to the party here but I was bartending in NY and watched this couple who had met on Tinder have their first date sitting at my bar. The girl was a complete maniac. Kept bringing up the fact that the dude she was with could be a psychopath and could murder her (he had given no indication of this) and went on Tinder while he was still sitting beside her at the bar.

She kept telling him he was lucky that she agreed to meet him at all, and she didn't think he'd be this boring. She ordered about 5 or 6 LITs and several shots, he literally just had two beers. She made him pay for everything.

My favorite part was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. Straight up thought he had disappeared out of the bar.

Cringeworthy Dates factsShutterstock

1. The Rank Smell of Rejection

A guy got stood up. He then drank a magnum bottle of red wine (8 glasses of wine) and ate three apps out of depression. His date called him, and he started cussing her out. He asked for more wine and then I had to cut him off.

So he got up and tried to run out of the restaurant with a bottle he grabbed from a rack. An off-duty cop tackled him in the lobby, and then he pooped his pants in front of everyone waiting for a table. He lied there screaming with the guy holding him down until the cops arrived and arrested him.

This is my fondest memory of being a bartender at Olive Garden.

Cringeworthy Dates factsPexels

Sources:  Reddit,

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