A Gentleman’s Valentine’s Day

When it comes to Valentine’s Day there are typically two distinct perspectives. On one side of the coin are the men who pull out all the stops for this one night; flowers, candy, reservations at the best restaurant in town. (My hypothesis is that some of these men are hopeless romantics on just this one night of the year). Then we have the men who think this is just a fabricated holiday created to give the economy its first post-Christmas uptick. I have found myself on both sides of this coin. On which side of the coin do you typically find yourself?

I don’t believe you need to find yourself on either side of this proverbial coin. My belief is that you should find yourself nowhere near either side of this coin; in fact, forget the coin and invest your time in loving your lady. A true Gentleman will seek to understand what his wife, girlfriend, or fiancé wants, and tailor this special night to her expectations.

“Love is giving somebody the power to destroy you, knowing that they will not use it.” Simon Sinek

Before I dive into discussing how a Gentleman approaches Valentine’s Day, I want to address the mindset that Valentine’s Day is just a “Hallmark Holiday”. First, let’s review the history of this holiday. The very first origins of Valentine’s Day are found in Roman society. Rather than February 14th, the celebration occurred on February 15th and was called Lupercalia, which was a fertility celebration. Around 496 Pope Gelasius the First changed the Pagan festival into a Christian feast day about love, naming it after a St. Valentine. For a more detailed description of this holiday, watch this video Valentine’s Day History. Now, I want to boldly address the thought process, “I don’t have to celebrate this holiday because its sole purpose is an economic boost.”


There are a few fundamental errors. I would like to start by asking you one question: How happy are you in your current relationship? Is your unhappiness with your relationship contributing to your negative perception of Valentine’s Day? I challenge you to self-reflect on this question (Self-Reflection is a pillar of the Gentleman Project). Also consider self-reflecting on the intent behind your Valentine’s Day actions using these questions:

  • What is your approach to Valentine’s Day? Is it similar to that of Christmas – during which many confuse the true meaning (the birth of Jesus) with a commercialized approach. Consider what you believe to be the true meaning of Valentine’s Day. It’s original intent was to celebrate love rather than maxed out commercialization.
  • Are you concerned about other’s perceptions of your actions or inactions during Valentine’s Day – about the gifts/non gifts that you give to your loved one?
  • As gentlemen we should NEVER miss out on an opportunity to cherish our wife’s, girlfriends, fiancés. If you elect to not celebrate this holiday, consider what it may mean to your partner (even if you have differing views of Valentine’s Day).

When we accept the idea that Valentine’s Day is just a “Hallmark Holiday” we’re also consciously saying no to an opportunity to express our love. This is NOT what we do as Gentlemen.

So what does a Gentleman do for Valentine’s Day? This will differ for each relationship because we need to customize the valentines-day-picturenight to the personality and wants of our loved one. I would recommend answering these questions while planning your Valentine’s Day.

  • What is your significant other’s love language?
  • Typically, do they enjoy a planned night in or an extravagant night out?
  • What’s something/somewhere they have wanted to do/go for a very long time?
  • When was the last time you sincerely thanked her for everything that she does for you and your family?
    • When was the last time that she had an opportunity to get dressed up and actually feel beautiful?

Gentlemen, I challenge you to go through these questions and truthfully answer them. Remember, that a Gentleman never misses an opportunity to cherish his significant other. Also remember we don’t do anything for the praise of others, but rather to make our partners feel special, loved, and cherished. If you’re going to go all out for Valentine’s Day ensure that it’s what your significant other would want and you’re doing it for them, not for the praise on social media. Gentlemen, put together a night (or weekend) to celebrate your love, make your significant other feel special, and to set an example of how we should love our wives.


The love of my life and why I strive  to make myself better!

Need Valentine’s Day Ideas? Valentine’s Day


What are your plans for Valentine’s Day?

What has been your most memorable Valentine’s Day, and Why?

Happy Trails

Thanks to my wonderful wife for the second pair of eyes and helping me edit this article!


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