I had a date with a great guy. I didn’t drink, but his wine added $36 to our bill. We split the check equally. Should I have spoken?

Dear Moneylist,

I went on a date with a great guy last week. We both ordered salads and entrees from a famous LA restaurant.

It was an exciting place to meet someone for the first time, and I kept my eyes peeled for names in bold. Believe me when I say that restaurant dates have been replaced by awkward walks in the park and coffee dates at Starbucks SBUX,
the past few years, so it was nice to dress up and have something to look forward to.

But – yes, there is a but – he ordered two glasses of wine, which cost $18 each. He had a Chardonnay with his salad and a Cabernet with his main course. I don’t drink during the week and was happy to drink tap water, but I don’t pass judgment on anyone who chooses to have a few drinks, especially on a first date.

His drinks added $36 to the bill, and I waited for him to say, “I’ll get the tip” or “You don’t have to pay for my booze” or even, “Do you want me to have the tip?” wine and pay for it separately? He didn’t do any of those things. Including tax and tip, that probably added over $20 to my bill. I paid my half of the bill.

Should I have spoken? Is it OK to ask someone else to pay for your alcohol?

First date

Dear first date,

I will divide this into two parts: Chardonnay Manners and Cabernet Dreams.

Let’s start with Chardonnay Manners: you did what you thought was right. You weighed the $36, excluding tip and tax, and figured it wasn’t worth the fuss since you liked this guy and were having a good time. But that leaves a hangover – ironic, considering you had no alcohol – and residual resentment over what you perceive as his lack of consideration. Go on a second date, and if you see a penny pinching pattern, show her the door to the wine cellar.

Now on Cabernet Dreams. What must he have done? If he wrote to this column, I’d say, “Offer to pay for the drinks, and if she refuses, tip 20% and make sure your date doesn’t add a tip.” He didn’t do that. Yes, it’s a bit rich to expect someone to pay for your drinks. A glass of wine ? I would let it go. Two glasses of wine? I would be on the fence, just like you. Three glasses of wine? I’d say, “I won’t pay for your wine, Buster!” And I would say that with a smile.

On a scale of 1 to 10 bad dinner stories, yours was 3. I saw dozens: there was the man whose friend pressured him to pay for a $150 sushi feast because his friend had fought over two of the tickets to a concert, and he expected to be treated royally for the favor. Then there are the stories of people who spend their time arguing over which friend paid for which dish. You like this guy and you still have time to establish the ground rules. Next time you will be prepared.

Be nice, be clear, and be assertive. These are all attractive qualities.

Related: Does the man always have to pick up the check?

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About Michael Brafford

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