An etiquette expert weighs in: When do you remind someone about an unpaid Venmo request?

Is it a dick move to remind someone about an unfulfilled Venmo request? 

When I was still in college a year ago, I split a pitcher of margaritas and a few baskets of chips with some friends. When the bill came around, we agreed it would be easiest for one person to put down a card and for everyone else to Venmo them. I got stuck with paying. While I signed the receipt, the rest of the group pulled out their phones and sent me their share. 

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Almost everyone. One person never sent me the $18 I was owed. 

I didn't notice until we were well out of the restaurant and on our way back to our dorm. It felt petty to remind them right away, so I waited to send the request until the next morning, adding a fun drink emoji in hopes that it wouldn't come off as passive aggressive.  Read more...

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