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How to ask a waitress out on a date

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There was a cute waitress that was serving me and my friend at a restaurant and we had a couple of pleasant exchanges with her, nothing out of ordinary and unusual. Then I asked her for a blank piece of paper and pen. She jokingly asked me if I was drawing something for her and I said yes. Even though my initial plan was to just leave my number, I decided to improvise and did this:

I left the piece of paper with the check and my friend and I left before she could see it.

We went out and it was fun.

A couple of things to keep in mind:

  • Make sure you leave your number like I did and don’t ask her in person. A restaurant might have a policy against giving out numbers or getting too comfortable with guests so even if she wanted to give you her number she might not.
  • Make sure you don’t use the check since it might be used later on by a manager to submit tips or something similar. Ask for a blank piece of paper that she can easily dispose of.
  • The above-mentioned 2 points also take care of all the objections that others raised in their answers. You aren’t making her uncomfortable. You already paid, tipped (tip as usual, don’t tip too much), and left. If she isn’t interested, which is the most likely scenario, she will just throw away your number and that’s it.
  • Get creative. Draw something and/or write something unusual. You will stand out from others that do the same thing.
  • Last but not least, don’t get your hopes up. Just leave your number and be happy that you expressed your interest. Whether she responds or not isn’t up to you, so don’t worry about that part. As I discussed with her above, it’s part of her job to throw away the numbers and apparently that’s what she did most of the time. I have tried something similar in a couple of other occasions and this is the only time it worked.

Good luck!

 

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