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Sunday, September 14, 2025
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GUY HAD DREAM DATE BUT ASKS HER TO SPLIT THE BILL

A guy shared a story of how he went out for a date with the girl of his dreams but made a big mistake asking her to split the bill when the waiter handed the bill over.

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The bill $10 and it got his dream date sitting there in a shock with stunned silence.

Here is the story

“This happened several years ago. I really don’t think about it much anymore but I figured I might as well share at this point.

I was introduced to my friend’s cousin who just so happened to be the most beautiful person I had ever seen. If I remember correctly, the first few times I saw her I got a nosebleed. No coincidence… Something about her I guess? Lol… The nosebleed wasn’t that bad though, but I would have to keep tissues around just in case I sneezed and made a mess… Didn’t happen… phew.

But this girl actually liked me. What a confidence booster! The thing is… I’ve always been horrible at asking girls out. The only chances I had were when I happened to see her after my friend invited her and his sister over to hang out. Didn’t happen much. But when it did, I still didn’t make any moves. I eventually asked his sister for her number. And she wanted to go out with me!

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I made plans to go to the zoo. And… it wasn’t all that bad. We had some things in common, not a whole lot, but some. Not the best chemistry, honestly I tried… But eventually we ran out of things to look at and do, so she wanted to go get food or grab a drink.

Rule #1: ALWAYS have a backup plan

I didn’t know where to go. But we made a quick decision to get some wine at this restaurant nearby. We head over, I open the door for her in an awkward fashion, go to our seats and just order two glasses of wine.

Now, trust me when I say this… I am horrible with wine. Or at least I used to be. At the time I didn’t drink it very often so I wouldn’t know when to stop drinking it. It would hit me differently than beer. Anyways, our conversation started out pretty good… then ok… then, well, you get what I mean. It wasn’t working out that well. Especially when she asked me if I liked pineapple on pizza and I said no. I think she put her head down in shame.

After that I noticed that she kinda lost interest. She was looking at her phone a lot, while I was trying to initiate conversation. Rude? A little, but I got the point after awhile.

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I ask for the bill. The waiter comes back around with the bill. I ask her if she wanted to split the bill. She insisted to split it. I probably should have paid the bill. It was just two glasses of wine. At the same time, in the back of my head, I knew it wouldn’t work out anyways. So I told the waiter that we’ll like to split the bill.

She sat there just looking at me with an awkward silence. It must have gone on for at least 10-15 seconds. What is going on? Is this a dream? I looked around to see if anyone else was looking at me like in Inception. Nope. It was real… I had no idea what was going on. I repeated, can we split the bill?

I already had my credit card in my hand and she took the card from my hand and handed it to the waiter. I was embarrassed from there on out.

So that’s it, no second date. Haven’t seen her much since. Yeah I should’ve just paid the whole bill. It was like $10 some more because of happy hour.

Rule #2: Insist to pay the bill on a first date, it’s not a big deal”

Image source: unsplash.com

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