The Art Of Making Memories

Why The Best Moments Are ALWAYS Unexpected

“person standing on rock raising both hands” by Xan Griffin on Unsplash

It reads like a postcard moment. Cool fall temperatures made the air feel crisp. Inconspicuous heat lamps kept us warm. Perched at an elevation above the tree line, we enjoyed a view with miles of visibility. Our server had just delivered a glass of red wine.

This description depicted the setting for our dinner last night. We chose a new, upscale restaurant. Everything was perfect. But then it all went to shit. A group of smokers, outside the restaurant, coupled with an unfortunate breeze poisoned the air around us. The restaurant was full, so we could not move to another table.

And Then The Shih Tzu Happened

A few minutes later, another couple waltzed in. The man dressed in a flashy, colorful shirt and wore sunglasses. He was slightly slumped over, probably from the massive amounts of jewelry hanging from his body. That didn’t bother me, but the little Shih Tzu dog he brought into the restaurant did; this was not a service dog. It was clear he brought it in for show. I didn’t think you could bring a dog into a restaurant, but I guess it’s okay at outside seating.

The dog behaved well until a server delivered food to a neighboring table. That got the little dog all riled up. The owner of the dog had the good sense to remove it from the restaurant. It caused a bit of a scene and was mildly entertaining.

Extraordinary Moments Catch You Off Guard

Were it not for the incessant smoke, the food, setting and unexpected entertainment would have made for a perfect evening. But the planned perfect moment rarely turns out perfect. Extraordinary moments catch you off guard. You never see them coming.

The most memorable moment from my wedding eleven years ago was when I screwed up the vows. Whenever we watch the video, we belt out a good laugh at that scene. I barely remember the cake or anything about the reception.

One of my favorite memories from my running days was a six mile run in the pitch black at 2 AM under a torrential downpour. I was somewhere in rural New Hampshire. In the midst of that run, I wanted to cry. Now, I look at it with such nostalgia; I want to cry.

I’ve been thinking about these memorable experiences the past few weeks and making a note of them in my journal.

The perfect moments happen unexpectedly. You can plan all you want, but the contrived moments lack something. They lack the visceral emotion of a thunderstorm in the pitch black of a neighborhood two-hundred miles from your home. The carefully framed wedding photograph lacks the embarrassment of screwing up your wedding vows and the release of tension that followed a collective laugh from the guests in attendance.

What’s The Common Thread?

It seems there’s a common thread here. The best moments in life come from the spontaneous, unexpected and emotional events. You can’t plan for it. You can only notice it when it happens and feel thankful that it happens at all.

How Can You Create More Of Them?

The answer is simple. The more activities you participate in, the more likely you are to experience something memorable. The more people there are involved, the more likely something spontaneous and emotional will occur.

Try New Things

I remember every highlight and lowlight of my first marathon in 1998. I ran ten more. Ask me about the fifth one. It’s more of a blur than a memory. I remember the first day of work at my current job. I don’t recall what happened yesterday.

Want to make a memorable night with your sig other? Try something new. It’s more likely to be memorable than going to the same restaurant you’ve been to fifty times.


What’s uncomfortable in the moment, becomes a moment of pride in the future. I was scared shitless of running in the pitch black in New Hampshire during a thunderstorm. Discomfort generates emotion, often negative emotion. For some reason, we look back on it with a sense of pride and nostalgia.


We planned for the perfect evening last night. We checked off all the boxes.
- Scenery
- Food
- Wine
- Setting
- Company

We ate a nice meal, tarnished by the smell of cigarette smoke, enhanced by the presence of a cartoonish man and his Shi Tzu. Will that unusual scene be enough for me to remember the evening? We’ll see.

By contrast, I’ll never forget the cheap meal at a burger joint last year. Why? I had to sign the credit card bill with a crayon. The restaurant had lost all of their pens. It was unusual and unexpected. My kids laughed uncontrollably — emotion. That makes it an experience that will remain etched in my memory forever. There’s a randomness to unforgettable moments that you’ll never be able to control or predict.

There’s a saying that we remember what’s important or what matters. I don’t think that’s accurate.

We remember what’s new.
We remember what’s unusual.
We remember what’s unexpected.
We remember what’s emotional.
We remember random weirdness.
Now, go make a memory.

Experimenter in life, productivity, and creativity. Work in Forge | Elemental | Business Insider | GMP | Contact: barry@barry-davret dot com.

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