66 Real Questions for the Valentine(s) in Your Life This Year
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.
How would you describe your mother? How about your father? How are you like (or not like) them?
Who were you in fourth grade? What parts of that person do you miss? Still have?
If you found out you had 6 months to live, how would you spend it? What would you do and whom would you do it with?
What is one thing you want to accomplish in your lifetime?
Is there anyone you wished you’d asked out at some point that you never had the courage to?
What do you think about marriage? Raising kids?
What’s the thing you fear the most? Stress about most? (besides spiders, snakes, or death)
When’s a time you were completely consumed in bliss?
What was your educational experience like? How has that shaped your view of how you fit into the world?
What would you do if you weren’t afraid? What do you think is truly holding you back?
Do you think someone’s political ideology says something about who he or she is as a person?
Have you ever felt like an imposter — like everyone thought you were someone you weren’t? Describe that.
Do you typically follow your head or your heart? Do you try and follow logic or gut first?
Have you ever been financially poor? How did you push through? What scars have resulted?
Did anyone ever tell you that you were smart? How about dumb? How has that affected your confidence today?
What’s a time that you made a quick judgment that eventually was proven wrong? What about a time you were proven right?
What do you believe is the biggest problem the world is facing today? Do you know the solution?
How would you describe your psychological framework? How do you see the world?
Do you believe humans are fundamentally good, bad, or somewhere in between?
Have you ever done something that you immediately regretted? What was it?
Do you consider yourself guarded (both physically & emotionally)? Why do you think you are that way?
Have you ever lost someone close to you? If not, do you fear it? If so, what was it like? And how is it today?
Do you think the best is behind you or ahead of you? Why?
Have you ever experienced a deep depression or a dark period? What was it like? Do you know what triggered it?
How does your creativity manifest itself? Do you listen to it?
Do you truly love how you are spending your time these days? If so, how? If not, what are you doing to change it?
When’s the last time you felt truly in touch with your intuition?
Do you believe in God? Why do you think that is?
When’s the last time you did something good for someone without telling anyone? What was it? (Tell me, please.)
What do you do when you are completely alone?
If you could project backward 10 years, what advice would you give yourself?
What is the biggest stressor in your life today? How are you working to overcome it?
Have you ever turned off or left your phone at home for an entire day? If so, how did that feel? If not, why not?
What is one thing you’ve had on your “to-do” list for more than a month?
Do you work too much or too little? How come?
What is your first priority? If I asked you to skip out on meeting your favorite celebrity to attend to it, would you?
What’s one thing you’ve wanted to learn how to do but haven’t made the time for?
Are you passionate about anything? If so, what? If not, why?
How do you feel presenting in front of a crowd? Do you typically avoid or seek scenarios where this is necessary?
Do you have any “open loops” or unresolved issues that are bothering you immensely? If so, why have you addressed them?
Are you religious? Spiritual? Indifferent? Do you celebrate any religious holidays?
What do you think you waste the most time on in an average day?
What is the meaning of all this? Why do you think you were put on this planet?
Where does your mind lead you in the shower, in traffic, or in silence?
How would you define unconditional love? Have you ever experienced it?
Where does all of your money go? Do you save? Do you spend more than you earn?
What’s a time you felt truly aligned, congruent, and fulfilled?
What makes a person successful?
When I say the word “guilt,” what comes to mind? How about “regret”?
What is your deepest desire that you have not spoken of?
Do you ever experience existential angst late at night? If so, what runs through your mind?
What do you do because you think you should not because you want to or have to?
What is something you’ve lied to yourself about recently?
What is something you believe that most, if not all, of your friends (and society) disagrees with you on?
Breakfast, lunch, or dinner? How come?
What is your “soul toupee” or the thing that everyone knows about you that you just can’t seem to admit?
What emotional, spiritual, and physical pains do you harbor?
Do you believe birth order shapes a person? Has it shaped you?
Who do you follow on social media or in the press in an almost “creepy stalker” way?
What makes you so sad that you get sick to your stomach?
What is the book that has impacted your life more than any other? Have you shared it with anyone?
What are you struggling deeply with right now in this moment?
When’s the last time you experienced unfiltered joy?
What is something that happened to you as a child that you may not have fully recovered from?
Are you the type of person that prepares for natural disasters, flees them, or doesn’t worry at all?
Have you ever been in love?
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.
