By Jerry Mooney

WHEN JERRY OPTED FOR A LOW-KEY HANG WITH HIS GIRLFRIEND, HE THOUGHT HE WAS WINNING ON VALENTINE’S DAY. UNTIL AN UNEXPECTED “GRAND PRIZE” RUINED EVERYTHING.

I want to start this story by clearly stating that I have no illusions about my level of maturity when these events happened. When I tell the story people ask me: Why didn’t you do this or why did you do that? I’m not defending my actions—although they were all done with more naivete than ill intention. What is clear is that I lacked what is now called Emotional Intelligence or EI.

While I was in my 20s, I met a woman on New Year’s Eve. We seemed to get along well and the night culminated in a midnight kiss that showed promise. This midnight smooch was not merely a champagne induced mash-session, we had a real connection.

Because we found the idea of seeing more of each other enticing, we exchanged information and began dating. This was before texting or any real application of email, so we called each other on the phone and met a few times a week. It felt like a fledgling relationship and we were both committed to sincere exploration.

The timing of our meeting proved to be a challenge though. Only six weeks into our fun-but-new romance came Valentine’s Day. Being that we had only known each other six weeks, this holiday offered up some fear. Riddled with insecurity as to how to proceed, I asked Jennifer what we should do on that day. She had the perfect answer: “Since this is all so new, let’s keep things mellow.” I was ecstatic that we were on the same page and offered to cook dinner at my place.

On Valentine’s Day I went to the store to buy the ingredients for dinner. This was before paying with debit cards at the counter, so I stopped into the bank that was housed inside the store to withdraw some money. Upon completion of my transaction, I was informed that I had won the Valentine’s Day grand prize!This was an ostentatious package of romantic symbols that would win any husband weeks of goodwill from their wives; but I wasn’t a husband, and my new relationship was far too vulnerable for such a grandiose assortment. The prize included a stuffed bear with heart shaped soles on its hands, lingerie (his and hers), champagne and crystal flutes, massage oil, chocolates, and the biggest bouquet of flowers I’ve ever seen including at least a dozen long-stem red roses. 

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I kind of panicked.

I had never won anything and suddenly I was faced with this expensive bounty that I felt should belong to someone else. I made a weak effort to decline the winnings. No go. So I took everything to my car, which took several trips, then returned to shopping. When I got home, I put everything away. The flowers were too big to stash, so I put them where they could be seen, but not on full display.

Jennifer showed up on time. She brought me a card that simply asked, “Will you be my Valentine?” with two boxes, one for yes and one for no. It was the perfect amount of gift for our situation. I found it cute and non-threatening. We chit-chatted while I finished cooking. As I was preparing to plate the meal, she was wandering around and saw the flowers.

“OH MY GOD! Are these for me?” She cried with tremendous excitement. Inside I was terrified. If I said no, then I had to explain that why I didn’t get her flowers and why I had these flowers and they weren’t for her. That seemed complicated. If I said yes, I might be coming on too strong and give her the idea that I was too clingy.

In a sit-com-esque fashion I said a weak “yes…”. She was thrilled with the flowers and I felt like I made the right call. She was warm during dinner, shooting me flirtatious glances and body language that indicated I was in for a good night.

I KEPT THINKING, I’M GLAD I SAID YES…

Jennifer spent the night and I felt like things were really heading in the right direction. It seemed I had dodged the bullet fate had shot in my direction, except for one little detail: I never saw her again. After that night she no longer returned my calls. Her sister asked me to leave her alone and it became clear that my over-the-top floral gift sucker-punched my future with her.

What I took from this is that romance is a dance. We have to constantly engage our partner to sense where they are, where they are going and not just dip them suddenly out of nowhere—even if they ultimately want to be dipped. We must communicate on a constant feedback loop.

Love hard, my friends.