“How are you still single?”  This is a question I’m asked more and more often the older I get.  I no longer take offense to the question, instead, I view it as a compliment that the inquirer believes I possess a handful of positive attributes!

The Pursuit of Growth lifestyle that I have committed to follow over the past several years has radically changed the way I view relationships, most notably changing my mindset from “What can a woman do for me?” to “What can a woman and I do together?”  I could write a Netflix miniseries documenting my ignorance, immaturity, dramatic failures, and lessons learned from my foolish past.  Perhaps one day I will!

But, before I invest total transparency in the many mistakes of my romantic history, I’ll share a short story of a Valentine’s Day failure that taught me a lifelong lesson.

Many, many years ago, I lived in an apartment above a neighborhood Italian restaurant.  The restaurant served amazing dishes, provided exceptional customer service, and presented an atmosphere of both sophistication and a casual dining flare packaged together for an incredible dining experience.

During this point in my life, I was invested in a dating mantra of quantity over quality (quite foolishly.)  My relationship goals focused on meeting women, persuading them to go on a date with me, and then quickly moving on to find the next woman who piqued my interest.  I thought by dating a vast amount of women I would increase my chances of finding “the one.” I will once again emphasize; I was a moron!

The law of the harvest states, “You reap that you sow.”  Well, I reaped what I sowed on Valentine’s Day.

I was introduced to an amazing woman at a networking event, and over the course of several weeks we met often for coffee or drinks and held stimulating conversations discussing ambitions, fears, goals, and life opportunities.  Each date was better than the previous interaction.  A few days before February 14th, I reached out to her and asked if she would like to join me for a Valentine’s dinner.  She accepted.  I was really excited because she was the type of woman who I envisioned myself pursuing a committed relationship alongside.

Over the past year, there was one restaurant that I would take nearly all my first dinner dates.  Yes, the Italian restaurant under my apartment.  It was selfishly convenient, and honestly, it was an amazing place!  It gave me the ability to practice dating laziness, as I could simply walk downstairs and meet my date for dinner at our agreed upon time.  I thought I was a genius.  Of course, I made plans to have my current Valentine’s Day date meet me at the best Italian restaurant in town, or perhaps, the most convenient.  I was prepared to impress her with an evening she would never forget.

Our dinner was exceptional.  The food was incredible, the atmosphere impeccable, and the red wine was delicious.  Our conversation was fun and flirty as I did my best charm her with my witty and clever banter.  I may have stupidly told a little white lie about wanting to bring a special date to this restaurant, and I was happy that she was the one who I could finally share the experience.  Okay, this wasn’t a white lie, it was a big bold faced lie.  As our perfect date drew to the end, the restaurant owner approached our table.

Due to my frequent patronage of his restaurant, the owner and I had developed a casual friendship, and he would stop by to shake my hand and often offer a complimentary dessert.   This evening was no exception.  He showed up at our table and greeted us with a smile that lit up the room.  Then, he made a loud and gregarious statement that was intended as a compliment, but instead, placed a dagger in my Valentine’s Day heart.

“My friend! You always bring the most beautiful girls to my restaurant, but tonight, you’ve brought the most beautiful one of them all!”

He walked back towards the kitchen and let our waitress know to bring us their signature dessert to ensure our evening ended on a high note.  But that was no longer possible.

“How many girls have you brought here?” my date inquired, her tone direct and full of growing anger.  “Is this like the place you bring all your dates because you live upstairs?  You’re an @$$%#*&.”

I had honestly not thought about it quite that way and how terrible it sounded, but, nevertheless, she was right, and I was busted.

My response was eloquent and precise, “Umm…I mean….well….it’s not like that…..okay, so…..yeah…..this is a good place, and I come here a lot…..but, like, no, why?….are you upset?”

Yes, she was upset.  She called for her ride and quietly sat at the table waiting for her escape.  I attempted to jump start the conversation with a few lighthearted questions, but I was greeted by simple “yes” and “no” answers.  A few minutes of silence passed, and her car arrived.  She politely thanked me for the evening and left the restaurant to head home.  Our evening ended abruptly, and I had no one to blame but myself.  I never heard from her again.

Many years later I think back on my Valentine’s Day massacre and realize there is a significant lesson learned.

Men, this lesson is for you!  Women want to feel special, unique, and important.  Just like you do!  When you behave with laziness and complacency, like unoriginally taking all your dates to the same Italian restaurant, you are setting yourself up for an epic failure and possibly a heavily accented Italian entrepreneur whose choice of words are more dangerous than a hired hitman.  Instead, if a woman agrees to spend a night out with you (with her precious free time by the way)  make sure you give her value back by putting a little effort towards ensuring the night is special, unique, and worth her investment. Especially if the evening in question is Valentine’s Day!  Finally, never, ever lie! It will always come back to haunt you. That’s what I learned from my epic Valentine’s Day failure.