It was an exciting venue to meet someone for the first time, and I kept my eyes peeled for boldfaced names. Believe me when I say restaurant dates have been replaced by awkward walks in the park and coffee dates at Starbucks
SBUX,
-0.58%
in recent years, so it was nice to actually get dressed up and have something to look forward to. 

But. Yes, there’s a but. 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 make no judgment about anyone who does choose to have a few drinks, especially on a first date.

His beverages 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 alcohol,” or even, “Would you like me to take the wine off and pay for it separately?” He did not 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 up? Is it OK to ask someone else to pay for your alcohol?

First Dater

Dear First Dater,

I’ll break this down into two parts: Chardonnay Manners and Cabernet Dreams. 

Let’s start with Chardonnay Manners: You did what you believed to be correct. You weighed up the $36, excluding tip and taxes, and figured it wasn’t worth making a fuss given that you liked this guy and had a nice time. But it leaves a hangover — ironic given that you didn’t have any alcohol — and a residual resentment over what you perceive to be his lack of consideration. Go on a second date, and if you see a pattern of penny pinching, show him the door to the wine cellar.

Now onto Cabernet Dreams. What should he have done? If he were writing to this column, I would say, “Offer to pay for the beverages, and if she refuses, tip 20% and ensure that your date does not add a tip.” He did not do that. Yes, it’s a bit rich to expect someone to pay for your drinks. One glass of wine? I would let it slide. Two glasses of wine? I’d be on the fence, just like you. Three glasses of wine? I’d say, “I’m not paying for your wine, Buster!” And I’d say it with a smile. 

On a scale of 1 to 10 of bad dinner-date stories, yours was a 3. I’ve had some 10s: There was the man whose friend sucker-punched him into paying for a $150 sushi feast because his friend had wrangled two free tickets to a concert, and he expected to be treated royally for the favor. Then there are the tales of people who spend their time arguing over what friend paid for what dish. You like this guy, and still have time to set the ground rules. Next time, you will be prepared.

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

Related: Should the man always pick up the check?

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