How To Have a Cheap Date, But Still Seem Rich

I recently started seeing this guy, let’s call him Nate*. And Nate was great.

Our first date was four hours of non-stop talking. We had the same tastes in TV shows, the same interests, and even skirted around the topics of politics and religion only to find out that we were on the same page there as well.

Our second date was even better. We went to a restaurant for wine and cheese, and after enough wine we started to get rambunctious and make off-the-wall jokes.


“How are we going to get rich quick?” I had asked him. And we swapped some ideas until we landed on this.

“Okay, it’s a rooftop,” he proposed, taking a sip of wine. “But we call it The Booftop Rooftop”.

I nearly spit out my Sauvignon Blanc. That’s exactly my humor.

“Yes!” I nearly shouted. “And instead of Happy Hour, you could have Boof O’Clock.”

“And you have to boof,” he insisted. “Even if you ‘aren’t boofing this week,’ you still have to boof.”

For those of you who don’t know what boofing is…I’ll allow Urban Dictionary to explain

Screen Shot 2019-06-26 at 7.06.02 AM.png

I left the date excited to see him again, and as we texted during the next few days, he asked me this:

“Have you been to Mermaid Inn on Second Avenue? They have a happy hour oyster/drinks special that we could catch the end of.”

And I broke up with him.

“A happy hour?” I told Bridget on Facetime later that day. “A special? We could catch the end of it? I paid $95 for our last date and now we’re going to catch the end of a happy hour special?

The truth was, I don’t think he was a cheap guy. I sneakily paid the bill while he was in the bathroom for the last date, and he was super nice about it. He paid for the first date, and didn’t show any signs of being cheap.

The honest truth was that I’m still hurting from my last relationship, and being super self-sabotagy lately. But that’s a lot harder to admit so I told myself “I am shallow!” and broke up with him because of his “cheap text”.

Ah, the human mind. So infinite in its glory! And so stupid sometimes.

But the whole situation got me thinking. It’s expensive to date. Especially for men, who are expected to always pay for the first date.


My brother recently got engaged (to the most amazing girl of all time), but I remember in the years when he was single hearing about the dates he went on, and how each date added up to be a pretty big monthly expense.

So how do you take a girl out on dates that don’t seem cheap, but actually are?

I’m putting my (and my friend’s) dating experience to good use, and letting you in on some Girl Approved Methods of cheap dates techniques that will make you appear rich without breaking the bank.

1. Always take her to Happy Hour, and never say that it’s Happy Hour


Humans are weird. We are all about perception and image, even though we try to pretend like we’re not. It’s just a weakness we have to accept.

So take your dates out to Happy Hours, while never uttering the words “Happy Hour”.

“Hey, want to go to Sister Jane at 6:00 for some drinks?”

You know that Sister Jane has Happy Hour from 5-7, but she doesn’t have to know that.

Once you’re there, you can make sure drinks are ordered from the Happy Hour menu by looking up the drink deals in advance and just saying “I hear this place has amazing Margaritas.”

Oh, what’s that? Margaritas are on the Happy Hour menu? You wouldn’t know! You haven’t even touched your menu yet. It’s just a lucky coincidence. You order the margaritas.

But you did know because you looked it up on Yelp, or stopped by the day before, or whatever.

Okay I’m getting way too into this. I’m talking about Happy Hour like it’s a war strategy, I promise I’ll be cooler for the next point.

2. Make a reservation for anywhere you go

I am always insanely flattered when a date makes a reservation. Even if we go into a restaurant that has many tables open, if my date goes, “Hi, we’re here for a reservation…LastName, party of 2,” I will start to get hot and bothered. There’s something sexy about a reservation.

And oh, look, there we go. I promised to be more chill in the next post and I’m talking about getting turned on by someone planning ahead. Just ignore me.

But the moral of this holds true. Maybe it’s because sometimes making a reservation costs money, or maybe it’s because making a reservation gives the illusion of exclusivity, I’m not sure. But either way, I suggest it. It’s a free way to seem super luxe.

3. Suggest a bakery date

It might be different in other places, but in New York City, a bakery item is almost always going to be cheaper than a cocktail.

Once again, the phrasing and invitation to this date is always important, so text your date something like, “Hey, want to explore Alice’s Bakery with me on Sunday? My co-workers were raving about it today.”

And then once you’re there you buy a doughnut or something. I mean personally I would buy like four and then make a fun little game of taste testing them since they’re cheap and you can now ball out, but it’s up to you and your budget.

4. Utilize “recommendations from your coworkers”


I cannot stress this enough! Basically it’s the tip from above.

You can suggest semi-cheap things, if you phrase it correctly. For example, asking a girl out to Ramen will give her the vibe that you’re cheap. We all remember Ramen as the 99 cent crap we ate in college.

But if you say, “Hey, my co-workers today couldn’t stop talking about this Ramen place in the West Village. Can I take you there this weekend?” it will give off a completely different vibe.

Chances are, you work at a company (haha). It’s probably a good company. When you reference your co-workers you could be referencing someone in their thirties or forties who has good taste. We think of co-workers as these refined business people we’ve never met, and it feels rich. In actuality, it was probably the summer intern who was like, “Bro, I got faced last night at Lee’s Ramen for $15” but I mean your date doesn’t have to know that.

Pro Tip: Say that your boss recommended the place. We’ll think you’re even richer, haha.

5. Do not suggest a coffee date ever


Coffee is a weird thing. I’m not referencing the fact that it makes me sweat and poop and gives me delusions of grandeur.

I’m talking about how coffee is deceptively expensive. And the reputation is the opposite.

I suggest not taking a girl out to coffee for two reasons.

The first, is that it seems cheap. I don’t know why, it just does! A coffee date? In the harsh light of the morning? I just don’t buy that people enjoy this as a dating concept.

The second, is that it will still run you a good amount, and it can’t last that long. Most people can only have a cup in a sitting, so you’re looking at a 30 minute date. And if your date gets a soy latte with foam and coffee art then like…boom. That’s 2 glasses of wine in the money world.

This one isn’t really a technique though, it’s more of my personal preference, so feel free to tell me to go fuck myself here if you want.

6. Suggest a lunch date


More places than you think have great lunch deals, so play this off like you’re asking a girl to a meal. Not lunch. A meal.

And once again, since it’s all in the phrasing, pretend like you’re booked for all of time except for lunch.

“Hey, I’ve got night plans for this weekend but I would love to see you. Are you free for lunch on Saturday?”

You know, you’ll seem busy and popular but also appropriately interested. And it’s not a gross coffee date. It’s a full on meal! Who doesn’t love getting a meal?

I hope you learned some good tips in here. Otherwise I just exposed how shallow I am to the world for nothing.

But again, and I stand by this, we are all shallow. Hate the game, not the player.

And if there’s anything I can really impress upon you, it’s phrasing.

If Nate had said, “Hey, want to grab a drink at The Mermaid Inn? I’d love to see you again,” it would have come across better.

Granted, I still have my hang-ups and am currently self-sabotaging, so maybe I still would have said no. But that’s on me. Ah, Nate. The boofer that got away, am I right? We all have one.

So get on out there, and fake your wealth!