The Groupon Dating Strategy Pays Off (Sometimes)
The Groupon Dating Strategy Pays Off (Sometimes)

The Groupon Dating Strategy Pays Off (Sometimes)

•  3 minute read

How to use coupons discretely while out on your first date.

Feel free to judge me. This is what I’ve done on two dates – I call it my Groupon dating strategy:

But if saving hacks are something that you can both get behind, sites like Groupon and Ebates are the perfect way to save money on nice dates and gifts for an anniversary, a birthday, or even Valentine’s Day.


The first thing I did each time was find out where the woman lived (if I didn’t already know) so that I could pick a nearby restaurant. Sitting in traffic can really put the brakes on an evening. Then I asked what type of food she liked: Italian, Thai, whatever. Next, her dietary concerns.


I met a vegan girl once. I’m really glad I asked, otherwise I would’ve risked taking her to one of those places with a giant rotating meat skewer.


After making sure these requirements were met, I got on Groupon. If there was a restaurant that met my checklist and had a deal on the site, I picked it.


The First Groupon Dating Attempt


The first time I did this, I managed to get the waitress alone long enough to hand her the Groupon and explain. That worked well.


There's almost no chance my date knew her lamb and cashew butter macaroni was 40 percent off.Click To Tweet


Although this whole issue did distract me from dinner somewhat…


The Second Groupon Dating Attempt


The next Groupon dating attempt was a disaster.


I took a different woman to a Thai restaurant where I’d never been. The opportunity didn’t arrive to discreetly give the waiter my coupon. But what happened next made me wish I had made an opportunity.


What I did was take the bill folder when it came and discretely inserted the folded-up coupon. This is when things got awkward. Apparently, the waiter had never used a Groupon before. He acted like he didn’t even know there was a promotion. He took it out in front of us, unfolded it and questioned everything about it.


Nothing is a bigger mood-killer than having a Thai man with poor English pointing at your date’s food and saying how much of a discount I may or may not be receiving.


Her sushi would not be discounted, I was informed. In retrospect, it’s kind of funny. At the time, though, I’m sure I was red with embarrassment. Ah, gotta love dating.


A Blessing in Disguise


You’d think that would have ruined the evening, but it didn’t. Well… maybe not.


My date went on to say how attractive she found people who “have their finances in order.” She talked about how she had been on her own financially since she turned 18.


Although the Groupon felt very much like an embarrassing disaster, it turned out to be an easy segue into that all-too-awkward point in a relationship when money gets discussed for the first time.


Final Thoughts


It’s been about a year since these two incidents, and I’m not dating either woman anymore. Maybe it was the Curse of the Groupon. Is that a thing? I kind of think it might be.

Curse aside, I’m split on whether or not it’s good to use a Groupon (or any type of coupon) early in a relationship. On the one hand, it feels cheap to use a Groupon. But there is nothing inherently wrong with it.


In fact, if a woman used a Groupon on me, I’d find it extremely attractive. It shows she’s money-savvy.


So far, I’m not coming up with any rational reason as to why using a Groupon is tacky.


If you want to use a Groupon on a date, I suggest stopping by the restaurant alone beforehand. Ask the host how you could get the deed done in a discrete manner. And maybe avoid Groupon entirely if you’ll be eating at an authentic Thai restaurant where some waiters have poor English and an even poorer understanding of the coupon economy.