My Date Paid For Dinner — & This Is How I Feel About It

Illustrated by Richard Chance.
The end of a date is, hopefully, full of feelings. But one of these feelings is more awkward than the others: Raise your hand if you've fumbled, engaged in the tried-and-true wallet reach, or said "oh no you shouldn't have" when a date insists on paying the whole bill.
The world of heterosexual dating can feel like the last frontier in overcoming old-fashioned gender roles and stereotypes. It goes without saying that you can be a hardcore feminist and appreciate when a guy holds open the door or picks up the bill on a date. Conversely, it shouldn't be emasculating to a guy when a woman offers to pay. But is it okay to feel a tinge of disappointment if you go dutch?
Let's face it: the bill on a date can be really awkward to navigate. There is a slew of factors to consider: If you know your date makes three times your salary, is it incumbent upon them to pick up the check? Or should you just split the difference the whole night no matter who makes what? And to what extent does ego play into the whole thing?
Ahead, four recent Money Diarists dive into how they felt when their dates picked up the check.

More from Work & Money

R29 Original Series