I offered to buy my friend a birthday drink. She ordered $180 worth of food and expects me to pay. Should I Venmo her for half?

By Aditi Shrikant

'My offer was cocktails'

"She ordered an appetizer, entree and two desserts, along with several cocktails."

Dear Dollar Signs,

I was invited to a friend's birthday party, but I couldn't make it. We aren't that good of friends but I do like her and would have gone if I was free.

Because I couldn't make it to the party, I offered to buy her a drink another time. She seemed excited and I was happy to spend more one-on-one time, as we aren't especially close.

When we were out for drinks, she ordered an appetizer, entree and two desserts, along with several cocktails. I was thinking maybe she was going to cover her food.

However, she seemed to think that my offer for drinks was an offer for anything she ordered. She didn't pull out her card and just thanked me for paying. The meal cost over $180.

I don't spend that much on friends who I'm actually close with. I want to Venmo her for at least half of her food, seeing as my offer was cocktails.

Is that petty?

Birthday Bamboozled

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Dear Bamboozled,

She didn't bamboozle you if she earnestly thought this was what you wanted, too. Still, it's always disappointing when a generous offer feels like it's been exploited.

I am curious as to how you presented what you were gifting her.

To be sure, your "friend" expecting you to cover a $180 meal is wild. Not even doing the performative card-reach for the food is bold.

But if you're not speaking up and setting boundaries, her assumption that your offer included dinner is just as reasonable as your assumption that it didn't.

Definitely don't Venmo half afterwards without discussing it. That could come across as passive-aggressive and might create more awkwardness in your wider circle.

Just because you know your intentions doesn't mean you specified them out loud. You don't know her super well, so it's also possible that she is operating with a different set of norms.

She might have grown up in a social circle where paying for drinks meant you were paying for a night out, no matter what that included.

While I understand the urge to request money, foot the bill and learn from this experience. Next time you offer to buy someone drinks - or anything, really - set the parameters first.

In this instance, you could have told her you're eating beforehand. Say something like, "Let's grab drinks around 8:30 p.m. I want to cook myself dinner before our fun night out."

Another option: Tell the server that you're covering drinks but you'll each pay for your own food. Even the most brazen birthday girl would have trouble doubling down on your paying for the whole meal.

Rethink whether you want to get closer with this woman. You said you were looking forward to spending more alone time with her, presumably to forge a deeper bond.

This experience might be a glimpse into what she expects from a good friend. But you are not, by your own account, a close friend. You appear to be one step above acquaintances.

If how she treated you over dinner made you uncomfortable, you don't have to pursue a relationship with her. You can keep her at arm's length and not make these kinds of offers again.

Write to Dollar Signs at dollarsigns@marketwatch.com.

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-Aditi Shrikant

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09-05-26 1137ET