Matchmaker Says: Cut The Small Talk

Are you tired of talking about the weather?

Boston based Matchmaker, Kenzie, reached out to the whole Tawkify team after reading this New York Times article about asking bigger questions on first dates. She was inspired by the notion of starting more profound conversations when getting to know a potential romantic partner, but also when meeting people for the first time in general. In her words...


Are you tired of talking about the weather?

Boston based Matchmaker, Kenzie, reached out to the whole Tawkify team after reading this New York Times article about asking bigger questions on first dates. She was inspired by the notion of starting more profound conversations when getting to know a potential romantic partner, but also when meeting people for the first time in general. In her words…

We so often stay in our comfort zone and ask the usual “what do you do for work?” and “where do you go on the weekend?” questions, but these often never give us answers that truly show us who someone is. I think for a few of my clients, their dates have come off as more like interviews and that isn’t the greatest basis for sparking romantic chemistry.

This excerpt from the New York Times article also provides some interesting talking points:

One of the common questions I find myself asking a woman on a first date is where she has traveled. The response can quickly become a list of places, and once again we’re in résumé territory. So instead I’d ask, “What place most inspired you and why?”

Rather than ask about her job, I would ask, “What work are you passionate about?”

I wouldn’t ask about her longest relationship, as if length equals depth. Instead, I’d ask, “What’s the most in love you’ve ever felt?”

NYC Matchmaker, Heartalytics columnist and travel blogger, Olivia, chimed in after Kenzie’s prompt with additional insight…

All humans want a genuine human connection.

I almost always have my clients (for one of their dates) bring their passports to meet up. And I tell them specifically to pick out two of the stamps and tell a story about their travels. I encourage all to do this–it has been successful. And it makes for the story–not the list! 

From our matchmakers’ mouths to your ears, daters! We dare you to date outside the box. Ask leading questions – like Michele instructed in What To Tawk About, a Heartalytics article published this past September. Discover each other through stories. Bring along something unconventional to spark an uncustomary conversation. The dates you will remember best are the ones marked by a bit of risk and a little whimsy – so have fun with it! 

Love, 

Team Tawkify

Art: “Conversation” by Dan McCaw

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