Are You Bored? Have You Been …. Boring? The antidote is here.

From time to time, has dating been for you BORING? Same old, same old? And a tougher question – Have you ever BEEN boring, to someone you’ve been with on a date? Not sure… well, you might actually ASK a few of your one-date-wonders why it was that Date Number Two never happened. Yep, that takes guts, but you might learn something if you dared to ask.

A better question might be – In what ways have you been boring, yawn-worthy, less than intriguing, dull or just not special or intriguing in the mind of the person who’s sat across the table from you.?

I’ll often hear from single men and women some version of this comment – I’m not bored or boring when I’m in the company of someone who’s interesting.  And if you know me at all, you’ll guess what I’ll say to that comment which is that the cart is before the horse, that it’s a chicken / egg issue.  The solution is to BRING your interest, your curiosity and your fully engaged self to each social encounter, to each conversation, to each date you have the opportunity to experience.

If you’ve ever been bored on a date, shame on  you…. If someone has ever been bored with YOU on a date, I say, that’s on both of you.

The antidote to boredom is … Curiosity.  Which is not “pretending” to be interested, but actually being present, bringing fascination and wonder to the encounter.  It takes practice. It’s a skill well worth developing into a superpower, as it will transform your experience of dating and indeed – it will transform your experience of being human.

Here’s a list of handy dandy questions that you can store in your phone or your wallet, to whip out anytime, to turn what could be an ordinary date to an extraordinary human experience.

Remember, the best way to approach each dating adventure is NOT to find out “Is this My Person?” – not at all. The vast majority of early connections (text, phone, Zoom or in person dialogues) will not make it past date number one, for a dozen reasons.

None of these early explorations is a waste of time, if you are contributing, allowing yourself to be contributed to, if you’re learning, growing and connecting in a meaningful way with each person you have the opportunity to meet.

Tell me something I don’t know about you.

Tell me something I don’t know about your day today.

Tell me something I don’t know about your kids / your parents / your preschool years / your freshman year in high school / your favorite teacher / professor / mentor.

Tell me something you’re proud of having accomplished.

Something you’re ashamed of.

What’s a silly thing you give yourself a hard time about?

What was your mom’s best meal that you can remember?

If you’re invited to a pot luck gathering, and need to bring something special, what would you bring?

What’s one of your dad’s best qualities? His worst quality?

What’s a state / city / country you’ve not yet visited and would love to see?

Your favorite national park / museum / landmark?

A type of communication that’s hard for you?

Who’s your favorite comedian?

One of your favorite movies (Comedy? Drama?)

Two songs on your current playlist or all-time favorite songs you never tire of hearing.

Favorite sit com Tv show you loved growing up. Sing the theme song….

If you’ll be on a twelve-hour flight, what would you plan for entertainment?

What’s your least favorite vegetable? Your favorite?

If you were stuck on a desert island, three people you’d want to have with you.

A food you have trouble resisting.

A habit you’d like to break? A habit you’d love to create, develop as routine.

Best way to get motivated when you’re having trouble revving up.

A silver lining of the Covid era.

Song your mom (dad, sister, aunt) sang to you as a child.

If you HAD to sing a song at karaoke, what song might you choose?

A poem you remember the words to (recite it….)

A Prayer / Blessing you remember (or make one up, on the spot!)


Have fun playing with these topics and questions. Share any others you love with me too.

I promise, if you bring this kind of curiosity and sincere interest to each of your dating encounters, you will never be bored and you surely will never be boring.

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