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How To Use Groupon On A Date Without Her Knowing

It’s always a point of contention between team thrifty and team ball-so-hard: To use Groupon or not on a first date.

If you’re on Twitter, like I am, you will see this debate pop up every six weeks or so. Some men and women agree their should be no shame in using a Groupon or any sort of discount available to them when out on a date. The opposition feels differently, with women thinking it’s tacky, and the men who are on their side saying if he really cared about the girl, he’d pay full price.

I fall somewhere in between both of these groups.

Do I think Groupon is acceptable to use on a first date? Yes.

Do I think it’s tacky? Yes.

Do I use it based on what I feel about the girl? No.

Did I use it on my first date with my girl? No.

But on our first date, we had Ramen at a glorified food court called Gotham West Market, and before you judge, even the sophisticated palate of Chrissy Teigen digs it.

I only bring up my first date with Gina to make a point: You don’t need to use Groupon to have an affordable date. Most places offering Groupon deals are expensive and giving you an option for it to be less expensive, which is not necessarily the same as affordable. Ivan’s Slurp Shop was a good deal without a Groupon, and if you’re trying to save some money on a first date, I highly suggest you seek out the charming yet budget-friendly places instead of deals on the high-end place.

Nonetheless, I understand some of you have a penchant for real tablecloths and linen napkins. I also understand the dilemma of having champagne tastes, or maybe that’s not you, but those are the type of women you like, and you have an orange juice budget. In your case, Groupon or companies like Groupon such as LivingSocial, are a game-changer, a life saver. I get it, and I encourage you to thrift on, kind sir, but must you be so reckless with it?

Absolutely not.

Let me show you how to pull of a Groupon without getting caught.

The first thing you need to know is no matter how you feel about using a Groupon, if you use it openly, you will be judged and the judgement may not be kind. I asked my girl if she would have gone out with me if I used Groupon on our first date and she didn’t hesitate to tell me there would not have been a second date. For some girls, it may not be a negative thing that you like a good deal, but it could be tacky, a turn-off, and a move that puts you in the penalty box aka the friend zone. If that doesn’t matter to you, then wave your Groupon in the air, and wave it around like you just don’t care.

But if you have gone through the trouble of seeking out a good Groupon deal to use on a date, you can go through the trouble of using it with some discretion.

Let’s use this deal I found as an example:


Notice the Groupon is intended for two people? That’s key.Try not to get a deal that restricts menu options, like this one or this one, which gives you a percentage off if your bill comes out to be a specific amount or higher. You want deals made for two people or ones that offer you a certain amount off your total bill no matter how much you spend.

Now with this deal, the next thing I would do is call up the restaurant and speak to a manager. Let them know you’re situation. You have bought a Groupon, and you want to use it for a first date. Be clear and honest with them that you don’t want it to be revealed to your date that you’re using the Groupon. If the managers are not jerks, they will help you out.

Get to the restaurant at least a half hour to 45 minutes before your date and introduce yourself to the manager, remind him you’re the Groupon guy. Make sure they don’t call you the Groupon guy. You are here early to make sure you’re about to execute the Groupon without any interruption. This is important:


With this deal I have here, I would ask the manager and the server what wines are offered for the tasting. Also, ask the management or the server if the appetizer they have listed ready by the time she arrives. It’s nothing they have to cook, so this shouldn’t be a problem. Don’t be shy or humble here. Tell your date you know they offer a good wine tasting and you two should give it a try. These two things will help make the beginning of the date feel like an experience.

The other good thing about this deal is there are no restrictions on the entree order, which means she can order whatever she wants and it won’t hurt the deal. You should ask them if the deal is null and void should she order a salad. If they say it is, when she asks what she should have, suggest every entree except the salads. As a matter of fact, remind her she can get salad anywhere. Chicken Milanese? Not so much.

This Groupon also comes with a bottle of wine. Tell the server beforehand to select a bottle of wine based on what she ends up ordering, and make sure the bottle of wine is within the limits of the deal, but judging by the fine print, any bottle on their menu will suffice.

Of course, some of you may be asking, what if she wants dessert or coffee after the meal?

That’s a great question, but not quite the loophole you think it is if you’re savvy enough. In general, I always suggest on dates, have dinner one place, and dessert/coffe another. So if she does suggest she wants either of those after-dinner experiences, tell her you know a spot, even if it’s a Starbucks (and it really shouldn’t be a Starbucks, but whatever), and suggest you should go there. This gives you two a chance to extend the date without extending your time there.

The last step may be the most crucial in terms of pulling off the Groupon date.

While you were planning everything before hand, you can ask the restaurant if they allow you to pay for the Groupon deal beforehand. If they allow that, slip the server and/or manager a $20 for their troubles. If they prefer to wait until after the meal, to ensure you don’t add any extra expenses, give them the Groupon voucher before the meal so your date doesn’t see the exchange and they charge you the deal price.

I understand this sounds like a lot of work, but like I said, if you’re going through this much trouble to even scout dating locations based on Groupon deals, you can take these extra steps to do it smoothly. Whether or not she’s the type of person who would judge you for using a Groupon isn’t important. What’s more important is you don’t give her a reason to judge you in the first place.


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  • Carissa

    I knew a big tip was going to be part of this plan!

  • Alicia Cuthbertson

    THANK YOU! Had this conversation a few weeks ago. Don’t make me feel like a “Groupon date” Some get it some will not. Great read, love the way you laid it out.