'The man was staring daggers': Big tipper tries to take back $100, so waitress humiliates him in front of his date

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Apr 7, 2023 5:00 PM EDT

This big spender was so sure he pulled a fast one on his dinner date, until his waitress foiled his plan. 

What's the biggest tip you've ever given? For most of us, it might be a $20 bill on a day you're feeling extra generous and flush with cash. It always helps out servers to tip, since their base pay is not usually very high. And of course, since servers rely so heavily on tips, big tippers make their entire day! 

This waitress rode an emotional roller coaster as she served this couple their meal. As she shared in an incredible post to r/TalesFromYourServer, she was serving one couple who were politely spending big bucks on their meal, from ordering expensive wine to trying the priciest entree. But the date was a sham — when it came time for the check, the man racked up a $300 bill, and even added on a generous tip for the waitress! Unfortunately for her, he had a nasty change of heart. This server got him back before he could pull out of the parking lot, and probably spoiled any romantic mood for that couple. 

Then, this bride-to-be is caught between her fiancé and his intrusive step mother, who keeps insisting on changing their wedding plans. 

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  • 01
    Furniture - 00 E 'Mark the tip down to twenty bucks Hun, I was just playing it up for my date. You understand.'
    via kayleigh harrington on Unsplash
  • 02
    Font - r/r/Tales From YourServer Posted by u/tamiraisredditing: 3 3 29 31 340 2 26 Guy tips big to impress date but returns afterwards to take money back
    via u/tamiraisredditing
  • 03
    Font - We had a guy come in last night with his date. Throughout the evening he was the picture of courtesy and good manners. He complimented me, thanked me every time I came to refresh waters or check on the table, made a point to be forgiving of a kitchen mistake, super extra nice. The dream customer, really.
    via u/tamiraisredditing
  • 04
    Font - I appreciated it but didn't delude myself that I was the source and figured he was just in a good mood because the date was going well - They were chatting, laughing, having a great time, so I assumed I was an indirect beneficiary.
    via u/tamiraisredditing
  • 05
    Font - He was certainly in some kind of celebratory mood because he was sparing no expense. He asked for our highest quality wine, she got our most expensive entree, he ordered one of every appetizer for her to sample when she made a remark that she was having trouble deciding, it was a real feast.
    via u/tamiraisredditing
  • 06
    Font - So the evening starts wrapping up and I get their check. I ask if they'll be together or separate. She starts to say "Separate," but he makes a big deal of saying, "Oh, are you kidding? Together, definitely together. You never have to pay when you're with me babe," and so on and so forth. Then slides me a credit card.
    via u/tamiraisredditing
  • 07
    Font - I get everything sorted and bring out the receipt. He fills it out and it came to $289.00 total. He doesn't even blink and makes a big show of leaving a $100 tip. He thanks me for my service and emphasizes what a lovely night they've had. Of course, a tip that size is exceptional, so I thanked him profusely.
    via u/tamiraisredditing
  • 08
    Font - He said there was no need to thank him and goes on a big tear about how under appreciated waitstaff are and to just think of it as a stand-in for all the ingrates who didn't treat me right, going, "Don't plan to tip, don't plan to eat out, you know?" Looking at the mesmerized girl the whole time and not giving me a glance.
    via u/tamiraisredditing
  • 09
    Font - I could care less where he was looking, I was looking at the upcoming hundred bucks. I thanked him again and said I hoped to see them back soon and that was that. So he helps her into her coat and off they go. Great night, I was riding high.
    via u/tamiraisredditing
  • 10
    Font - About 90 seconds later he's back in the door, without her, going "I think left my-" then when the door shut and, looking to make sure she was out of ear shot, he goes, without the slightest shade of shame or embarrassment, "Mark the tip down to twenty bucks Hun, I was just playing it up for my date. You understand." And turns to go.
    via u/tamiraisredditing
  • 11
    Font - Uh... I understood, but not how he hoped I would. But I couldn't make a scene in the middle of work, that's not my place, so I just said one more time in order to give his conscience a chance to sink in, "Ok Sir. You'd like to amend your tip from one hundred dollars to twenty dollars, is that correct?" And even though I didn't show a hint of displeasure in my voice he shot back, extremely hostile, "Yes, and if I see a cent over the twenty on there I'm going to dispute the whole meal with
    via u/tamiraisredditing
  • 12
    Font - The most frustrating part of this for me was not even going from an over 30% tip to under 10%, but rather that this poor girl was being strung along, with no idea of who the guy was behind her back. It was extremely manipulative of him which is a major red flag. I've had my fair share of toxic relationships in the past and really wish someone had pulled the blinders off my eyes, so desperately wanted to do something to alert this girl to the trick the guy had pulled, hoping it would be a
    via u/tamiraisredditing
  • 13
    Font - But, again, I was at work and that just wasn't my place. So I altered the bill and that was that. Then, just in time, something occurred to me and I darted outside hoping to catch them in the parking lot. I got lucky. They'd parked on the street instead and he was still dealing with the parking meter.
    via u/tamiraisredditing
  • 14
    Font - So, I flagged him down and rushed across the street, nearly stumbling into traffic in my haste for a delicious moment. His date was already in the car but rolled down her window, since no one expects the waitress to follow you out to your car waving her arms like a crazy person.
    via u/tamiraisredditing
  • 15
    Font - I made it across and said, more than loudly enough for her to hear, "Sir, we amended your tip from $100 down to $20 as you requested, but you'll actually need to fill out a different receipt reflecting your new total for our records. Your old receipt still has your original tip of $100 written on it, but since you just came in and asked us to charge you $20 instead, we can't have a discrepancy in our records. I hope you understand. This is just a bookkeeping regulation that goes way above
    via u/tamiraisredditing
  • 16
    Font - His jaw was on the floor. He tried to pretend as though he didn't know what I was talking about, trying to give me some line about, "I think you're after someone else, I'd only come back cause I'd forgot my keys." But I would not let it rest. The more he played dumb the more I repeated versions of "You wanted to change your tip from $100 down to $20, you came back in," and on and on.
    via u/tamiraisredditing
  • 17
    Font - So we went back and forth for a few more seconds when finally he went, "Ok, whatever, uh, sorry for the miscommunication. If you need me to fill out a new receipt I can." And I, totally even keeled was like, "You only need to fill out a new receipt if you want to change your tip from $100 down to $20." And I'm guessing he didn't have the money in his account because... he did it. He filled out the new receipt. His girlfriend was visibly shocked and the man was staring daggers through me,
    via u/tamiraisredditing
  • 18
    Font - It was vicariously quite satisfying in place of the other toxic men I never did get that confrontation with. And all the bad tippers. Ironically the exact kind he made a righteous speech decrying just a few minutes beforehand. And then off they drove, I'm sure never to patronize our restaurant again, but hopefully never to go out together again either, which would make it totally worth it.
    via u/tamiraisredditing
  • 19
    Font - Shawofthecrow Great way to get back at him. I would've said no problem and kept the $100. He signed it, so the dispute would fall
    via u/Shawofthecrow

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tips liar date server revenge Awkward dinner waitress tales from your server dating
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