Businesses fail for the strangest reasons.

In early 2014, after a profitable but enormously stressful run, my business was officially closing its doors. We had made it work for three years, but with a lot of structural mistakes. I was ready for a long vacation and a fresh start.

I came up with an idea I was excited about, wrote a business plan, performed market research, and secured enough funding to keep my family fed while I built it. It was called Kimosuave, and it was going to be my next chapter. We developed a logo and some slick technology loosely based on Pandora's music genome. Everything seemed to be falling into place.

However, Kimosuave was not to be. Against all odds, my previous business, the one that was supposed to die, survived. My partner (a great guy and lifelong friend) wanted to make a go of it, so I gave back all the money, and once more unto the breach we went.

So what does this have to do with Valentine’s Day? Well, Kimosuave was a romance-oriented startup, and in the course of market research, we interviewed hundreds of women in an attempt to gain insight into female romance preferences. And gain insight we did! The research method was not the most scientific, but the results are real, and useful, and most men find them quite surprising.

Today I am sharing them with you.

The Mechanics of Sucking at Romance 

There was a study published in 2011 on two thousand married men, and it shined a light on just how deficient we are as a group when it comes to managing long term relationships. 55% couldn't remember their wedding anniversary, and there was a strong tendency to procrastinate until the last possible moment and then resort to gas station flowers on the way home from work.

(Pro Tip: don’t do that. She definitely knows. Later in this post, I will show you a much better strategy for handling emergency romance scenarios).

In our study, we also talked to quite a few men. We learned that about half of men feel, to one degree or another, overwhelmed by their romantic obligations, and at the bottom 20% of the continuum there exists a group that is truly rudderless. I call them the Romantically Impaired.

Most of these men went through a period of trying, but have a mental block when it comes to romance. They seem to have a hard time thinking about it, and as a result their failures hit them from out of nowhere. The block, which in an otherwise healthy relationship can be anything from a reluctance to show vulnerability to anxiety caused by past failures, also prevents them from perceiving a path towards improvement.  Eventually, most of them throw up their hands in bewilderment and stop trying. Even then, they do find girlfriends and spouses willing to deal with their romantic ineptitude, but it’s clear that their relationships would benefit if they could unravel this part of their life.

It’s worth noting that even among men who claim to have this part of their life under control, many still reported a history of forgetting anniversaries, which was also noted by women – 58% said that their men have forgotten at least one important event. This may suggest the presence of the Dunning-Kruger effect, a form of cognitive bias where an unskilled person is unable to recognize their own incompetence.

Lest I paint the picture that men as a gender are deficient, I should say that about half of men seem to do a satisfactory job in the romance department, with about 30% getting the highest possible marks. But it’s the bottom half that intrigues me. Why are so many otherwise competent men bad at this?

The best theory I was able to unearth comes from the work of psychologist and author Dr. Herb Goldberg. Goldberg says that men are wired to focus on external threats and pressures of the world outside of our "safe" relationships.

"In earlier times that meant hunting dangerous game and defending the homestead from marauding tribes, but today is more likely to mean getting that promotion and ensuring that Jones from sales doesn't get it," Dr. Goldberg says.

Whether that’s true or not, the expectations remain. Indeed, the expectations are evolving rapidly thanks to Hollywood and the romance industry, whereas men… Well, let’s just say we continue to evolve at the same rate we always have.

(Sidebar: 88% of women said that the romantic expectations placed on the modern man are reasonable. Which makes sense… They’re the ones who define the expectations. At the same time 58% told us that their men have a history of failing at or completely forgetting romantic events such as Valentine’s Day, and 70% said that the modern man is “barely successful” or “unsuccessful” at keeping romance alive.

Clearly, either we aren't doing a good enough job, or the expectations have lost touch with reality. Probably both.)

Hallmark, Hollywood, and Hershey: The Bar Raisers 

Ever wonder how big Valentine’s Day is? This year, the National Retail Federation expects Valentine’s spending to reach an all-time high of $18.6 billion, an average of $130.97 per American.   

All told, men spend over $50 billion annually on flowers and romantic gifts, and much of that is stressful last minute shopping.

It’s clear that a lot of men are terrible at romance. That’s one problem. Another problem is that the romance industry has an incentive to generate artificial romantic pressure, and a well-funded marketing machine to make it happen.

If you need an example of how they’re tampering with your relationship, look up Sweetest Day. There’s a reasonable argument that Valentine’s Day is more than a contrived consumerist blowout since it can be traced all the way back to 18th-century England, but Sweetest Day is clearly a marketing ploy. And it’s officially observed in eleven states.

But that isn't a free pass to neglect your relationship. There are ways to improve, even for the most hopeless among us. Read on.

Hand-Written Notes: The Key to Winning at Romance

If you take one thing from this post, let it be this: it’s all about the notes.  Check out these data points:

  • When asked to rate gift preference for various romance events, hand-written notes came up first in all categories except for mother’s day. For mother’s day it was spa gifts by a nose, followed by hand-written notes.
  • 86% of women said a thoughtful note can save an otherwise unimpressive gift.
  • 77% of women said that it’s very important or important to receive a note along with a gift.
  •  In follow-up Q&A, almost every woman agreed that a note written on notebook paper or stationary is more effective than a greeting card!

So here’s the takeaway: it’s a good idea to actually build your romantic gestures around the note. If you get that right, everything else is icing on the cake.

what makes a note work?

Nick Offerman, the actor who played Ron Swanson on Parks and Recreation, tackles this topic with characteristic precision in his stand-up routine:

Go to your printer. There’s paper in there. Take one sheet, fold it in half, and draw a heart on it. Sign your name and write I love you.

The bonus tip is to go outside and get a piece of nature. A shell or a leaf. Put that in the center of the heart, and then get stretched out, because you’re going for a ride to the realm of coitus.
— Nick Offerman

Solid gold. If you like that, you should buy his book, Paddle Your Own Canoe. The man is a chair-making genius.

But what about flowers?

Flowers work for most women, as long as you back them up with a hand-written note. The note that the florist puts on there is not enough.

Here are the insights that we gleaned:

  • Most women enjoy receiving flowers, but about 15% do not. A very small percentage really do not, so make sure you know who you’re dealing with!

    Here’s a simple way to find out: ask her what her favorite flower is. She might tell you, or she might say she thinks all flowers should be scoured from the face of the earth. Either way you've gained valuable intel.

    By the way, in many cases flower-hate is the fault of the man, not an innate issue with flora. If you pick up flowers from the gas station on the way home from work and that’s the extent of your effort, she knows and may resent your lack of inspiration. Be careful… You may be building your own flower hater.
  • There are many methods of getting the flowers to the woman, and not all are created equal. Personally delivering them at home along with a hand-written note is by far the most popular, followed by professional delivery at the office. Professional delivery to the home was least popular and appears to be a clear-cut anti-pattern.

The Emergency Romance Playbook

Does this sound familiar? You’re driving home after a tough day at the office, and out of nowhere you remember that it’s your anniversary and you have absolutely nothing planned.

Panic. Vertigo. Chaos and defeat.

First, ask yourself if there’s time to make last minute plans and rescue this thing. Sometimes that’s possible, but sometime it isn't.

The best you can do during an epic fail like that is put pressure on the wound and initiate some very delicate damage control. Take a deep breath, find a Walgreen's, and write the most soulful hand-written apology slash declaration of love you can muster on short notice. Your shaking hands might ruin a few drafts. If she likes flowers and they’re available, that’s a plus. Consider making up for it by promising to do something amazing for her every weekend for the next month (and then following through).

It happens to most of us at one point or another.  Godspeed. 

Update:  tl;dr? Here's the general gist, with pictures:

You can’t win on Valentine’s Day

These words came out of the mouth of one of the women we spoke to, and it resonated so forcefully that it permanently changed the way I think about romance.

She meant that if you don’t work on your relationship throughout the year, in between the major romance events, the stakes will be so high on Valentine’s Day that failure is virtually guaranteed.

Think of it this way. You don’t grow a tree by pouring gallons of water on it once a year and then starving it the remaining 364 days. As with a tree, your relationship needs a very small amount of preventative maintenance. If you neglect it, you will be unable to enjoy it because your attention will be occupied by bringing it back to life.

So what do I do? WE'VE established that I’m bad at this.

If you want to improve and you’re feeling blocked, you’re going to need a system and some good habits.  Open up your calendar right now and schedule four random romance drops over the next year, making sure none of them fall within three weeks of a known event such as a birthday or anniversary. 

On that day, you will produce a hand-written note and a gift. Flowers are ideal if she’s a flower person, otherwise the data suggests that spa gift certificates are great, followed by indulgences such as her favorite candy or meal. Extravagant gestures and lingerie ranked last.

That’s it. If you do these things, you will have upped your game to such a degree that Valentine’s Day might actually become an enjoyable experience. You will have very little to prove. The pressure will be off because you won’t be trying to cram three months of work into one high-pressure day.

Dodging Valentine’s Day

Early in my marriage, I was responsible for, shall we say, a series of mishaps. Looking back, I must have been flirting with the Romantically Impaired category even though I considered myself advanced.

One strategy we implemented was dodging V-day altogether. Instead, we created a celebration of our own on our pre-marriage anniversary. It feels less forced, the pressure is lower, and it’s much easier to get dinner reservations. It works for us.

If you try this, you should still give her a hand-written note on Valentine’s Day. Think about it: everyone around her is being showered with flowers and gifts, so she's likely to feel left out. Considering that you aren't supposed to do anything at all, even a minor gesture here can put one in the win column.


I wrote this post because I don’t want the Kimosuave research to go to waste. It was time consuming and expensive to gather, and a lot of work went into the analysis. The resulting insights opened my eyes and I hope it helps others. A number of others contributed, including my amazing wife Ellen, Josh and Mindy Young, Nathan Childress, and Jake Kelly. 

It’s also worth noting once more that this is targeted at long-term relationships and marriages, and is definitely not a guide to casual dating.

If you benefit from this, or if you have any thoughts at all, please drop me a line and let me know. Thanks, and good luck on Valentine’s Day!