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Braving the Financial Minefield of Dating

   Posted On: May 1, 2013  |    Posted In: Love and Money  |     Posted by: Broke Millennial®

One of my first “real” dates occurred in April of 2004. I was 15-years-old and a high-school sophomore and he was an adorable 17-year-old junior. We saw “The Aviator” (the Leo DiCaprio flick about Howard Hughes). Halfway through the movie our pinkies touched and a jolt of electricity went through my stomach. A few minutes later he was holding my hand and I silently prayed my palms would stay dry. I remember how he walked me home and went in for a kiss as I went in for a hug. He had about a 11 inches on me so a slight head bump was involved. We giggled nervously before he tilted my chin up and gave me a kiss. I remember so many vivid details of my first date, but I don’t remember who paid for the movie tickets.


(He was such a stud-muffin before the peeing in jars scene.)

Politics and economics are tame compared to the controversy, drama and polarized opinions one unearths when discussing dating protocol. After being asked several times to address the topic of dating I decided to broach the discussion in a true millennial fashion, via Twitter. True to form, millennials responded with a variety of opinions about the financial implications of going on a date.

Here is what I learned:

  • Some women think men should pay for the first date.
  • Some women think men should pay for the first several dates.
  • Some men think they should pay for the first date.
  • Some men think the women should offer to help pay for the date.
  • Some women will always offer to split the check.
  • Some women feel empowered by helping pay for a date.
Some women are willing to ask a man out and offer to pick up the tab.
  • Some men will let a woman pick up the tab.
  • Some women think the person who makes more money should pay.
  • Some men thinks the person who makes more money should pay.
  • Some women are willing to discuss their financial situation on a first date.
  • Some men are willing to discuss their financial situation on a first date.
  • Some men don’t want to go to a Knicks game, unless it’s to boo the Knicks.
  • Putt putt is a fun frugal date.
  • One reader thinks my blog is “dope.”

Confused yet?!

Optimized-golf pic

(I am both dope and an excellent mini-golfer.)

Personally, I’m in the “always offer to go dutch” camp. I’m pretty positive my 15-year-old self offered to buy my movie ticket. I’m never likely to turn down a free, well, anything, so the joy of having a man pay is great. However, it isn’t a deal breaker for me if he takes me up on the offer to contribute financially. Now, if a man asks me out and then expects me to pay, that would be a deal breaker. But, I haven’t really had to worry about it for a while.

I’m in a long-term relationship with a man I’ll refer to as Peach. We started dating my senior year of college and have always been pretty frugal with our dates. In fact, I distinctly remember a Valentine’s Day date in our campus dining hall. Peach paid for our first date, but these days we either split 50/50 or I force him to let me pay. I’m the working girl in the big City while he’s plugging away at grad school.

Erin and Joey

(We did not get this dressed up for our date in the dining hall.)

We’re also in one of those much beloved long-distance relationships. He’s pretty much the entire reason I’m a card-carrying Greyhound Rewards member.

Optimized-road rewards

(Told ya so. Check out the post “Finding the Glamour in Greyhound” for details on cheap travel.)

Between being young, poor and paying for trips to see each other, we have very few pennies leftover for elaborate dates. Here are some of our fun, frugal dates (noted in cost per person):

  • Visiting donation admission museums ($3-$5)
  • Student tickets to a Mets game ($10)
Mini-golf in TriBeCa ($5)
  • Picnic in Central Park ($5 spent on food)
  • Walk around Central Park (free)
  • Exploring new parts of the City (free)
  • Walking around Little Italy ($3 – Peach just had to get a cannoli)
  • Admiring the Christmas Tree at 30 Rock/decorations on 5th Ave (free)
  • Attending a taping of The Late Show with David Letterman (free)
  • Guided tour of the New York Public Library (free)
  • Pumpkin picking/pumpkin carving in his hometown ($5)
  • Apple Fest (his town) ($5)
  • Our big treat date: student rush tickets to a Broadway show ($25)

Optimized-pumpkin picking

(A big pumpkin and two little ones were still several bucks cheaper than most small NYC pumpkins.)

Optimized- pumpkin carving

(I got to gut the whole pumpkin and taught Peach how to bake pumpkin seeds.)

Optimized-30 rock tree

(After this photo we promptly fled the scene. Slow moving tourists drain all my Christmas spirit.)


(He was super excited to wake up at the crack of dawn to wait in line for the cheap tickets.)

Dating can be a hassle and dating can be expensive, but there are lots of fun ways to pinch pennies while enjoying each other’s company. Unfortunately, there can be a large upfront cost (especially for men) when dating in a major city. Particularly if you want to date around and frequently meet people out for dinner or drinks. To that end, I suggest getting creative. I would appreciate playing a round of mini-golf on a first date or taking a stroll through Central Park and getting an ice cream. For my first date with Peach we went on a nature walk through Rock City Park (a park with large rock formations).

Optimized-Rock city

(Rock City Park only had one trail…)

Planning an upcoming date? Be sure to check out deals on Groupon, Living Social or using relevant apps such as ScoutMob.

What are your cheap date ideas? How do you deal with the finances of dating?

As a straight female discussing my dating experience, I recognize this post has a heterosexual bias. All dating experiences are encouraged to be shared in the comment section below!

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47 responses to “Braving the Financial Minefield of Dating

  1. curious how you arrive at these nyc destinations, as it isn’t figured into the price. it may be free to walk in central park, but it would cost you 2.50 to get there and 2.50 to get back…. (from your address). “getting there” adds up big time in the big apple. (p.s. always enjoy following your blog journey) xo

    1. That is a good point. I, personally, don’t consider transportation cost because I pay for an unlimited monthly card. However, Peach doesn’t so depending on his length of stay we put money on a card or buy a weekly unlimited. Once we’re in Manhattan we do a lot of walking to avoid costs. For example, last week we walked three miles from the middle of Central Park to a restaurant in Harlem.

      In an effort to keep costs fair, we always split the price of travel to see each other. So if he pays $80 for a round trip bus ticket to see me, then I pay $40 worth of “NYC fun.” Typically, I put money on his metrocard to compensate for splitting the travel costs.

  2. Great post! There really are a ton of surprise expenses that can show up in dating — especially in New York City — that it’s nice to see a lot of frugal ideas consolidated together.

    I’ll refer back to this for sure if my dating ever gets past the courtship phase?

    1. Thanks! The comment above called out the great point of transportation as a hidden cost. If you both live in NYC and have unlimited metrocards it isn’t a concern, but out of towners have to pay per ride. Let me know if you have any other frugal date ideas!

    1. Haha this is true! It could be an excellent way to weed people out. As a hyper-competitive person myself it’s a great exercise in self-control.

      I sense a good story might be behind this tip. I hope you include it your own dating post!

      1. TBH, I’m reluctant to do anything except drinks on a first date. And by drinks, I mean alcoholic, not coffee. It’s not as expensive as dinner and easier to get out of if it’s not going well. If that goes well, second, third, etc dates can be more creative. 🙂

        For all you NYCers out there, I know the best kept Happy Hour deal in the city. There’s a little unmarked bar in the East Village where almost everything is $2.50 before 8 pm 7 days a week. I often suggest it for dates, especially when I know the guy is a bit broke (as am I) because everyone can afford to be generous at those prices!

        1. What’s the name (or cross streets)? I also agree drinks are generally the best option on a first date. But depending on the location and how well it’s going it can get expensive in a hurry.

  3. My first date with Steve was to Starbucks. Call Starbucks pricey if you want, but it was under $4.

    We dealt with more cultural issues in regards to paying for dates. He was taught that the man pays for everything, I was pretending I was never hungry because I didn’t want anyone to pay for me. Eventually, we both became more comfortable and paid based on who recently received a paycheck :).

    Obviously, it all worked out. We still go on cheap dates these days. A couple days ago we did a 5 mile walk to and from the park and yesterday we went out to a local bar for dollar beer night. I’m a big fan of cheap dates, especially with alcohol involved!

    Great post, other Erin!

    1. Thanks for the feedback other Erin! 😛

      If you just get plain coffee Starbucks isn’t too bad. Once you enter the frappachino world it’s a drag on the wallet. The paycheck scheme is a good one, especially once you enter an exclusive relationship and aren’t just casually dating.

      Dollar beer night?! Living the dream.

  4. Nice post! My wife and I were long distance ourselves…she was in L.A. and I was in Omaha. It sucked on one hand, but it really forced us to learn how to communicate with each other and be wise in our spending when we were able to see each other. Of course, I could only hold out with the whole 1500 mile distance thing for four months, so the rest is history. 🙂

    1. Long distance really does weed out the weaklings! Learning to communicate has been a great experience that will certainly be wonderfully beneficial in our future. We’re hitting two years of long distance in a week (YIKES)!

  5. What a great-looking couple you two are – you seem very happy together. 🙂 I’m pretty old school and think the guy should pay for the first date, but during the second date he asked about drink specials at the bar and it was then that I became smitten. These days we’re homebodies, so a “splurge” is going to happy hour for appetizers, watching a movie (I get discounted tickets at work), and then frozen yogurt afterward.

    1. Awww, thanks! We are a pretty happy-go-lucky couple.

      I remember discounted tickets! We had $5 ticket deals at our university. I sure do miss those. Happy hour apps, a movie and (well ice cream not fro yo) sounds like a splendid evening to me.

    1. Really selling the idea of marriage and kids! 😛

      I’m thinking that’s about a decade away for me so I’ll make the most of my frugal dates for now!

      1. Ha. Julie is right. We have 2 kids, 6 and 3. The older one is thoughtful, very careful, introspective and obedient. The younger one hurts herself 59 times a day from running around like a nut. She was a late talker, but now, she can’t go for more than 6 seconds without speaking.

        Its all in good fun though. I think the key is just to enjoy life at whatever point you’re at.

        You’re wise to hold off on kids though. Go nuts and see the world or whatever you want to do. We waited until our 30s and wouldn’t have done it any other way.

        1. My parents were both in their 30s when they had me so I always assumed I would wait until 32+ and just never gave it a second thought. With friends starting to get married, it makes me realize more and more that isn’t the life path I’m ready for. It’s beautiful for them, but I’m just not prepared for it. Plus, I don’t want a boy living in my space!

  6. Great post Erin! I guess I am old fashioned because I have never had a girl pay for a single date. It was expensive for me, but that is how I was raised. I loved your cheap date ideas and I’ll probably do several of them when I am in NYC later this month. 🙂

    1. Thanks, Nick! Feel free to email me for more fun NYC date ideas (or kid-friendly plans if you’re bringing your daughter).

  7. Awwww can you and Peach be any cuter Miss Erin? 🙂 Like Anna, I’m old school as well and think the guy should pay for the first date and anything afterwards is fair game or go dutch as you say! Long distance relationships are hard but I’m glad that you two are making it work, even on a budget! J and I don’t go on as many “dates” as we use to when we first started dating but when we do, we always try to use coupons for 2 for 1 admissions or find frugal outdoor activities.

    1. I’m thrilled the weather is getting nicer so we can go back to fun outdoor dates. Nothing wrong with being a little old fashion! Getting a first date paid for is certainly a fun perk of being a woman. 🙂

  8. Great post! I’m glad you still go to theater when funds are tight. I think the splurge on those $25 student rush seats are way more worthwhile than the $13 movies.

    1. Thanks! I agree, Broadway show is way more worthwhile than a movie. I also love supporting the theater. We go to the occasional off-off-off-off—way off—broadway show too. Plus, all the comedy shows, sketch shows and free improv shows NYC has to offer.

  9. I love being creative with frugal date ideas…I need to remember the pumpkin thing this fall because I love carving them but have yet to do so with my BF because we totally missed the Halloween boat last year!

    1. Carving pumpkins is so fun! Oddly enough, I was much better at the “gross” process of gutting the pumpkin than Peach. I like the squishy pumpkin guts feeling!

  10. I love the fact you began by reminiscing about a middle/high school date. Brought up memories of my first official date. On my date we saw the remake of Sum of All Fears with Ben Affleck (terrible movie) and I felt like such an adult paying for both of us. In fact it was the fact that I paid for both of us that made me think of it as a date in the first place. I did chicken out on kissing her at the end, but I eventually forgave myself.

    But just a pro tip for teenage guys just starting out, movies don’t make for good first dates.

    1. First date stories are great!

      Movies are okay if it follows an initial dinner date. Just going to the movies sort of defeats the point of getting to know each other. Not much talking happening there. Although, if you’re friends to begin with I guess it isn’t so bad.

  11. Me and my husb still go on cheap dates, and did when b4 we were married. I prefer it! This is horrible, but I can’t remember my first date now without really thinking hard. I remember my main bf in high school, and our first date… hmmmm, i feel old! Cheap is the way to go though, the amount of $$ spent on a date means very little. It’s about getting to know the person.

    1. Yup! It’s about the experience and really just talking and learning about each other. Personally, I don’t need that to happen over a fancy dinner. Don’t get me wrong, splurge dates can be fun, but I’ll always be happy with mini-golf and an ice cream cone.

  12. I’ve said it before, but you are just ADORABLE! It’s been a lot time since I’ve dated so undoubtedly the rules have changed a bit. I’m old-fashioned, so I would expect him to pay for first date (assuming he asked me) but I would also offer to split the bill. He would win extra bonus points if he refused. And win even more brownie points if he also let me pay the entire bill sometimes too. 🙂 Dating can be expensive, but the expensive things to do generally mean crowds at bars or silence at movies, so the things you’re doing actually allow you get to know a person. And who wouldn’t want to be with someone who has a sense of adventure and willingness to explore the city. Peach is lucky to have you. 🙂

    1. You are always so nice, Shannon!

      I’m glad Peach also loves exploration, and doesn’t mind walking to save a few bucks.

  13. I have to admit, I’ve only dated my current girlfriend. Whenever we first went out we would usually split the costs, then later took turns. Now that we’re living together out date nights might as well be counted similarly to any other couple that manages their finances jointly.

    Since we live in a college town, there were tons of cheap/discounted things to do as students. $5 movies, discounts on food in certain places, etc.

    1. $5 movie tickets were amazing back during our college days! Peach and I are probably 4 or 5 years away from living together, but plenty of my friends have started living together (and getting married). While I’ll always offer to go dutch, I’m a bit more old fashioned about living together.

  14. My first “date” with Mrs. JM was in Iraq. It was a dinner date at the free chow hall that we had eaten at a million times before that, but it was the first time it was just us. That’s pretty much how the first 6 months of our relationship went 🙂

  15. BF and I like to take long walks around town, exploring different parts of the capital, and perhaps end the day in our favourite coffeeshop, or have gelato at the marina if the weather is nice:-)

  16. The whole dating world is very confusing indeed! I expect the man to pay for a first date but don’t mind a cheap one. A walk, a free art show then coffee or ice cream is fine by me. And you can walk at any time, whereas a 3 course meal…

  17. Ha! Quite the variety of opinions. It’s been a while, but with my first date, I thought I should pay. But my then-girlfriend would get upset and always insist she pay her portion. My next girlfriend, I thought I should pay – AND she agreed (which often left me broke). My next one agreed to split the bill and I agreed and we lived happily ever after. Now, it really doesn’t matter who pays the bills, it’s coming out of both our pockets. And with a little one now, I find we’re doing more frugal dates as we’re always looking for ways to keep her occupied (walks to the park, library, apple picking, etc.). Great post!

  18. I once did a choose your own adventure date where we had coffee at the first coffee place we walked by, dinner at the first restaurant, and dessert at the first dessert place. This didn’t end up being very frugal, but it could be if you stopped by food carts and the like.

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