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A Valentine's Day Reminder in Thoughtfulness

In light of Valentine’s Day and in the spirit of gift giving, I thought this might be a good time to refresh everyone on how to pick a thoughtful gift, and how to avoid a Hallmark blunder.

But before I do that, the best way for me to help you understand the HOW, is to help you understand the WHY.

In all my years of dating, probably one of the most thoughtless gifts I ever received was a gift card for a full body massage...that was visibly addressed to someone else.

The name “Bam Bam” was scratched off and my name was written in.

As you can imagine it was an awkward situation for me - especially since the gift was from someone I had been dating for several months.

I wasn’t sure what the protocol was for handling it.

Do I be honest and say something or does that look ungrateful?

Do I not say something and just assume this was a “dumb guy” move?

Let’s be real: Regifting is a very practical thing to do, but the art of regifting is in the rewrap to ensure the item has a new and personalized feel. Since this was clearly some kind of mistake, I decided to skip the awkward “why did you give me this?” conversation and took matters into my own hands.

I called the massage parlor and asked when the card was purchased, and as it turns out, the card had been purchased 14 months prior.

Intrigued by this faux pas, I decided to investigate further.

Since social media is a wealth of passive information, I decided to go back to the month and year of when the massage gift card was purchased, to see if there were any internet clues on my then boyfriend’s page. Thanks to the help of his Venmo transactions and Instagram posts, it didn’t take me long to put two and two together that the gift card was originally intended for another woman and “Bam Bam” wasn’t exactly platonic.


It’s the opposite of thoughtfulness and the proof that two minutes of thinking can change a result.

Needless to say, this wasn’t a gift that made me feel good - even when given in unintentional error. To be clear, thoughtfulness does NOT need to be a grand gesture, but it does require an extra step of thinking.

Some options for my then boyfriend might have been:

-Get a new envelope to put the card in

-Throw out the envelope all together and put the gift card into a handwritten note

-Or simply say “hey I had actually gotten this a while ago and I’m not going to use it, would you like it?”

In my opinion, the most special gift a person can receive is something that is specific to them. Something that showed you were paying attention. Something that showed you cared. We often like to think that a thoughtful person is one who is considerate enough to give us what we ask for. However, we often react as though a thoughtful person is one who thinks of what we would want on their own, and gives us that instead.

The first scenario doesn’t actually require real “thoughtfulness,” now does it?

In my line of work in the dating industry, I coach men to be more thoughtful all the time. I teach them to pay attention to details, emotions and facial expression; to be curious and ask better questions; and most importantly - how to retain this emotional information they receive. For example, if your partner loves a particular culture or food, why not try making a themed dinner? Or if they’re homesick for something reminiscent of their hometown or from a particular era of their life, get them something that would encapsulate that memory. These are the small gestures that go a long way.

The process is completely individual but the best way to know what to do is to listen, pay attention, and remember. Write things down if you must. That’s it.

Happy Valentine’s Day and good luck!

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