Six Cheap and Memorable Dates

It’s been more than 20 years since my now-wife and I started dating. Along the way, we’ve been on countless “dates” – nights where we’ve chosen some kind of activity and done it together. Some were memorable, some were not.

Whenever a date was particularly memorable for some reason – and there were memorable ones very early in our relationship and memorable ones in the last few months, too – I would write about it in my personal journal. Personal journaling – writing down the events of the day and, more importantly, reflecting on them and reflecting on the things that happen to be on my mind at the time – is something I’ve been actively doing almost every day for the last … 25 years. (Yep, I got my first “journal” and a basic guide to journaling as a Christmas gift from my grandmother in 1991.)

I actually really enjoy looking at my old journal entries. In about 2008 or so, I digitized all of them, but I still handwrite new entries (and scan them all into my computer every once in a while). This means I can easily search them for words like “date” and “Sarah” and see what comes up.

Recently, I was thinking about frugal dating. Dating is often seen as a pretty expensive thing to do – the expense of a nice dinner and other date activities can be really costly, especially on a limited budget. Yet, when I thought about it for a moment, I recognized that a lot of the memorable dates with Sarah that came into my mind were actually pretty cheap.

Here, I’m going to talk about six memorable dates that Sarah and I shared that were incredibly inexpensive. Many of these were basically free; I don’t think any of them involved spending more than $5 plus the cost of a few inexpensive food items that add up to maybe another $5 or $10.

It’s worth noting here that some of these date ideas won’t be impressive. If you’re trying to impress a potential partner with an inflated idea of your financial largesse, these ideas won’t help. However, I will say this: unless you want a relationship that’s fueled by constant spending, you shouldn’t be trying to impress with constant expensive dates. Sure, an occasional expensive dinner is fine, but if that’s your routine, it’s a routine that’s going to leave you cash strapped for life and stuck with a partner that expects that kind of constant spending.

Anyway, here are six memorable and very low-cost dates I had with my wife.

Public Concert and a Picnic

A local band of some renown at the time gave a free concert in the largest park in the city where we lived. Your “price of admission” was a donation of an item for the local food pantry.

We went to this concert, taking along a few items from my pantry to pay for the admission. I took a backpack with me, which contained a blanket and a simple picnic dinner. During the opening act, we spread out in a far corner of the park where we could still hear the music and enjoyed a simple meal together – nothing fancy.

Our plan was to eventually pack up the bag and get close to the stage for the main concert, but as the evening wore on and the sunshine gave way to the stars, we realized our blanket was pretty comfortable, so we just stretched out there, side by side, listening to the live music and looking up at the stars for hours.

Pizza, Movie, and a Blanket

I spent an entire day working in a cornfield, while Sarah spent that whole day working concessions at a country music festival (the 1999 George Strait festival, to be exact). It was about 11 o’clock at night, but we were both still awake and energetic and wanted to spend a few hours together doing something. We met up outside of the concert venue and walked home together, right by a grocery store.

On the spur of the moment, we stopped in that grocery store, bought a $3 frozen pizza and a $2.50 tub of ice cream of a flavor we both liked (peanut butter cup), and then we stopped by her apartment. Her roommates were out of town, so we both took showers while the pizza was cooking, snuggled up under a blanket with slices of pizza and that ice cream tub and two spoons, and watched Starship Troopers (which has long been our favorite “popcorn” movie). We both fell asleep under the blanket while the movie was still running.

It was so simple and ordinary, but yet that night sticks in my mind like few others.

A Borrowed Tent

While we are avid campers these days, it wasn’t all that long ago that we didn’t even own a tent. Our first real weekend together, in fact, involved a night of camping at a beautiful campsite – the Lake Red Rock Recreational Area in Marion County, Iowa.

We borrowed a tent and two sleeping bags from a friend, grabbed our pillows and a few random food items from around the apartment we shared, and drove the relatively short distance to go there. We reserved a campsite for the night for $8, found some firewood that had been abandoned, and started a cozy fire in the evening.

There are few things more romantic than just sitting together around a campfire on a night with just a bit of chill in the air, a clear night with a new moon in the country where you can see thousands upon thousands of stars. That was our night at Lake Red Rock. We sat out there next to the low fire until dawn, and it was that night that I became convinced I wanted to marry her.

Picnic and Wine on the Hilltop

Shortly after we were married, we decided to go on a long hike at Ledges State Park here in central Iowa. For those who may perceive of Iowa as a flat stretch of cornfield, Ledges would completely shatter that myth for you as it’s loaded with tall hills, sheer ledges, and a narrow valley in the middle. If you like to go on trails with lots of inclines and gorgeous views, Ledges is a great place to go in Iowa.

Anyway, Sarah and I decided to pack a few sandwiches and some cold drinks for lunch in a quiet backcountry area of the park, and that’s what we did, except that I packed an additional small surprise. Wrapped in the middle of the picnic blanket was a bottle of $2 Charles Shaw wine (some semi-sweet white variety) and two plastic wine glasses.

We hiked on the trails throughout the morning, taking pictures of the natural beauty and of each other (we both like unposed photographs of people). We eventually found this amazing lookout point over a small river, so we spread our blanket, ate our sandwiches, and sat there for a little while, just gazing out at the river. I then opened the wine bottle, poured both of us a glass, and she rested her head on my shoulder.

Eventually, we found our way back down off of the hill with hundreds of wonderful pictures taken and some warm memories of the day, and it cost about $3 for the sandwiches and $2 for the bottle of wine.


Sarah and I had made arrangements to go out to eat at a really nice restaurant in Des Moines. We had reservations and dressed up nicely and headed out on the town.

Yet, when we got to where the restaurant was, we discovered that it had gone out of business sometime in the previous few weeks. We talked about just getting back in the car and going home, but we decided to just wander around in the area on foot.

We got lost in conversation. We bought something from a food truck for dinner for $5 or $6 and split it. We walked through a park and watched some people setting up an art installation. We talked. We held hands. We laughed.

Eventually, we realized we were completely lost. We didn’t know where to go to find where we had parked our car. We ended up wandering around a several block radius, trying to figure out where we had parked and laughing at this misadventure.

We walked by three or four places with live music and stopped a bit to enjoy it and ask where the restaurant was. Eventually, someone kindly pointed us in the right direction.

The funny thing was, we got to see and explore a lot of things that we would have never seen if we just went to that restaurant. We thoroughly enjoyed each other’s company for several hours. It only cost us about $5 for that item from the food truck.

Getting lost turned out to be a really great date night.

Planned by Children

Last year, on our anniversary, we told our children that Sarah and I wanted to have a date night… but we wanted the children to plan it using what they could find around the house. We gave them very little guidance in the matter and, while they planned things out, we spent a few hours outside working in the garden and doing other such chores.

The children planned a charming little candlelight dinner for us with salad and soup and sandwiches and cake. They picked out a movie for us to watch, made us sit next to each other, covered us up with a blanket, and turned off the lights. They brought us some popcorn and then a bowl of ice cream. After the movie, they played some songs for us and insisted that we dance together to those songs, then they chanted for us to kiss each other.

It cost us nothing, but I have never, ever felt an evening that was so full of love, both in the love Sarah and I share, but also in the mutual love that we have for our children and that they have for us.

Final Thoughts

All of these dates have a few key things in common.

First, the dates were memorable because they were more about Sarah than they were about the activity we were doing. The activities, while fun, became backdrops; the memorable part was being with her. I find that, on many expensive dates, the activity becomes the focus and not the other person and that’s a shame. If there’s real love there, the best dates are all about the other person.

Second, the dates were memorable because of the variety. Some took place in nature. Others in large cities. Some were planned. Others were complete happenstance. One even involved our children. The theme here is simple: try lots of stuff. Sure, some will be disastrous, but even those often turn out to be great (like getting lost after finding out that the restaurant you wanted to go to was out of business).

Third, the dates were memorable because they weren’t pressured. All of these dates weren’t highly scheduled. They were very much in a “go with the flow” mode, where we had maybe one single thing in mind to do together and the amount of time it took was quite variable and unpressured. We had time to let serendipity strike.

So, if you want a frugal and memorable date, try to do something different than the norm (look at the community calendars and to the services nearby for a good place to start), give it plenty of breathing room without strong time demands, and give your focus to the person and not the activity. If you enjoy the other person’s company, something enjoyable will always spring forth, even if you don’t spend a dime.

Good luck!

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Trent Hamm
Trent Hamm
Founder of The Simple Dollar

Trent Hamm founded The Simple Dollar in 2006 after developing innovative financial strategies to get out of debt. Since then, he’s written three books (published by Simon & Schuster and Financial Times Press), contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.

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