Hey Everyone,

Paying on dates is tricky territory. We’ve all been through that awkward dance at the end of a first date, right? There are a lot of options for how to navigate that reaching-for-the-bill moment that I talk about in depth in my Mindful Dating 101 course (including a great tip for women that I think is the best solution out there). But what about Venmo etiquette?

To some of you this might feel so intuitive that you’re surprised I’m writing a newsletter about it. But to some of you, this is completely uncharted territory. I know this because a friend of mine who is a confident, competent dater asked me last week if it was okay for him to Venmo request his date for her portion of their drinks, the day after they’d had their first date and he’d footed the bill.

Can you guess my answer? It was a big, resounding: NO! On early dates, keep Venmo out of it. Maybe someday Venmo will be the norm… but for now, it’s transactional in a way that doesn’t belong on the first few dates. And if you and your date haven’t even discussed Venmo as an option? Then charging someone out of the blue is an even bigger faux pas!

Happy Dating!

Alyssa

p.s. Don’t forget to sign up for my next CLOSET CLEANSE WORKSHOP this Thursday at 12:30pm EST! Learn how to do a post-pandemic purge, plus the 15 essential clothing pieces every wardrobe needs. Only $25.

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