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Dating FAIL: He Asked Me For the Tip

Author

Ava Hudson

Updated on March 29, 2026

Last night, my sister went on a date with a guy she'd met through an acquaintance. My sister and her date are both successful professionals in their 30s. They went to Taco Tuesday at a nearby Mexican restaurant. A lot of places in this area host Taco Tuesdays, and everyone knows it means like, $2 tacos. It's awesome.

When the bill came, her date said, "Is this right? Can you check this?" She was like, Okaaaay; she felt weird looking at the check, since most people, when you're their guest, are discreet about the amount. Still, she checked that the itemized bill showed exactly what she ate. When she confirmed it was right, he said, "Do you have the tip?"

Who says that? My sister was surprised by his request—and his sneaky approach—but she played along. Reaching into her wallet, though, she didn't have any cash on her. She was like, "Actually, I don't."

He replied, "Well, maybe you can get the next one." She shrugged and said, "Okay." Later, she asked me, "Is this his way of getting me to go out with him again? Does he only want to go out with me just so that he gets a return on his $4 investment?"

I say he's cheap. Of course it would have been fine for her to pay the tip, or get movie tickets if they had gone to the theater, but you offer to pay, you don't get asked. I've always found splitting bills unromantic. Better to take him out and pay in full or cook him lasagna on a later date where you invite him.

I think guys made up the term "gold digger," which definitely applies to a few women, but now it's overused. The term is in everyone's subconscious and the result is that it makes girls feel bad at every single exchange of commerce. I mean, the tip on a $2 taco? We're negotiating this now?