Dear Helena,
I am trying to be proactive about online dating, so I’m going on a lot of first dates courtesy of I always treat on a first date, and not at some hole in the wall either. I’m also really into Groupon. But if I take a girl out to dinner, will I look cheap if I ask the server to apply my Groupon?
—Tight-Fisted Romeo

Dear Tight-Fisted Romeo,
Using a coupon on a first date is like asking for a doggy bag—it ruins the atmosphere. Yes, in both cases you’re demonstrating thrift and foresight, valuable qualities in a mate. But it’s best to wait until the third or fourth date to show this side of you. A knack for fiscal planning is important, but it’s not sexy. Unsurprisingly, Mark Kelly, co-owner of Tree in New York, says daters are embarrassed about using coupons, whether from Groupon, BlackboardEats, Scoutmob, or another site. “Guys will come up to me [and ask me to apply a coupon discount]. They say, ‘I do not want you to bring the check to the table; I do not want to see it again.’ And I’m like, ‘I won’t blow your cover.'” So yes, if your date doesn’t know you well and you use a coupon, he or she may well think that you are cheap. As Patti Feinstein, a dating coach, says: “It’s a bad sign, like being rude to the waiter or undertipping.”

While I’m on the topic, let me clarify some other points of coupon etiquette. Firstly, there’s no need to tell the restaurant you plan to use one when you’re making the reservation or when you get to your table. They shouldn’t treat you any differently if you have a discount. At Tree, says Kelly, “They will get the exact same experience.”

Second, if you’re dining with friends and you get the check, you should apply the discount to the group’s total, not just to your own share. You look stingy if you say, “I’m applying my Groupon to my half, which means I owe $15 and you owe $35.” Plus you risk blighting the end of the meal with petty math. It leaves a bad taste if you force your friends to break out their phone calculators after dessert. That’s why I recommend always splitting the check equally, even if one of you just had water and a salad.

If you insist on keeping your coupon to yourself, you should dine solo. Or else do as Joyce Handley, creator of the blog Haochi DC, advises: “Grab the check and say, ‘I’ll get this; you get the next one.'” That way, you can reap the benefit of your investment, but you look generous rather than mean. (Obviously this only works if your friends are the type to remember when it’s their turn to treat.)

It goes without saying that you should tip on the prediscount amount (the same way you should tip on the full amount if a restaurant comps part of your meal). As Kelly explains: “As the restaurant, we have decided to discount the food. The servers haven’t decided to discount their wages.” If you weren’t already aware of this, Groupon reminds its users to tip on the full price, and Kelly says he rarely has a problem. The restaurant should not do as Dressler in Brooklyn allegedly does: enclose a reminder with the check. (The restaurant did not respond to my requests for an interview.) Even if you print the reminder in an elegant copperplate font, it’s still tacky to tell your customers how much to tip.

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