66 Real Questions for the Valentine(s) in Your Life This Year

My love next to “love.”

Quick caveat: This article is not wildly romantic. It’s sappy and honest, sure, but if you are looking for 50 shades of sensual prose, move on to the next one. This article is for the “old soul.” The book worm. The hopeless romantic — who likes homemade cards, candlelit dinners at home, and deep conversations on Valentine’s Day.

Because in my egotistical opinion, today should be about celebrating all kinds of love, not just the intimate kind. That’s why I’ve decided to have a bunch of Valentines this year: my dad, my girlfriend, my brothers, my best friends, and even some people I’ll meet on the street today.

I’ll treat them each differently but I will love them equally. Because today, like everyday, should be about loving more and loving better. And love does not spontaneously appear, love is a conscious choice. A series of choices actually — to plant seeds and cultivate them day in and day out. With friends, with family, with strangers, and with romantic partners.

It’s choosing to do the dishes late at night, when your spouse has to get up early. To read between the lines when your brother yells at you. To apologize (even when you think you are right). To have really hard conversations. To provide support even when you’re hurting. To find canvases for others to paint on. To just shut the hell up sometimes. And to always believe the best in people.

But it’s even more than these micro-decisions to give time or energy. Love is choosing to know a person. To see them, hear them, and deeply, even if for a fleeting moment, understand that they are more than what they say or do. It’s subtle and kind. For like everyone’s favorite neighborhood watchman, Mr. Rogers used to say: “There isn’t anyone you couldn’t love once you’ve heard their story.”

I try (and fail) to subscribe to that belief all the time. To push past the urge to judge someone on the surface by their words or actions. To believe that there is more than meets the eye. To listen more to what isn’t being said than what is.

I try to picture the old, drunk man falling all over me — breastfeeding. That obnoxious Trump supporter — being beaten as a child. The woman screaming at her child — finding our her husband has stage 4 cancer. And in these (hopefully fictional) realities, it’s impossible not to love them.

That’s what today is about: all kinds of love, even when its inconvenient or hard. Even when we are tested by “cat-calling” strangers and thoughtlessness from the people we are closest to.

So, how do we do it — how do we love more and love better? Not weird breastfeeding visualizations (I promise).

It’s simple: we ask better questions. And really listen to the answers. Pull out the really good stuff. Build a profound understanding of a person by listening to the stories of their struggles, losses, and heartbreak. Asking about their shame and guilt. The role models they had (or didn’t have). Their mistakes and shortcomings. Their resilience and strength. Their ability to laugh and cry.

So today, on Valentine’s Day, I’d like to share 66 questions from a lengthy list I keep of the best I’ve thought up or heard others ask to really learn about each others’ truths. 66 questions I truly want your answers to. Or maybe you want answers to. Or maybe your Valentine(s) want answers to.

66 questions to inspire a bit more empathy, understanding, connection, and unconditional love in your world today. I urge you to ponder, ask, share, or answer them. And to just simply: enjoy.

I dare you. Go out there and ask a question or two today. To a loved one or a stranger. Just be prepared to be amazed by the answers. Or maybe you’ll consider sending me just one answer at kate@staydressed.com. Happy Valentine’s Day to all you sappy people out there. I love you, truly.

Thinking deeply about how to make myself and the world a little better. & writing about creators mostly | email: kate@onedayent.com

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