I banned three questions at my college reunion


October 9, 2026

hey team,

Small talk kills me.
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I feel physically lethargic the moment someone starts a conversation by asking what I do, or how the weekend was, or how the day is going so far. So when I was heading to my 25-year college reunion last spring, I knew I had to go on the offensive. Otherwise, it was going to turn into me answering a million questions about my job and living in Oregon and similar generic things.

I also knew my classic conversation starters would be pretty weird in this scenario. I couldn't just walk up to someone I hadn't seen since the Clinton era and ask, "Hey man, what books are you reading right now?"
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I needed questions that could thread the needle between not totally weird but not totally predictable.
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So I did what anyone who is friends with a renowned behavioral researcher would do: I left her a rambly voice memo pleading for help -

I don't have many rules in life but I do have this one: when Vanessa Van Edwards offers you conversation advice, you take it. Her suggestions sounded good to me.
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Two days later, my college roommate Buckno picked me up at DCA and we drove down to Richmond. I ran through the plan with him.
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​We are not asking anyone where they live, we are not asking how they are doing and we are certainly not asking what they do for a job. I will scream if I hear anyone say "debt capital markets."
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(we went to school with a LOT of finance bros).
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Instead, we used Vanessa's questions, plus a few of our own. Net result? I had some of the deepest and most meaningful conversations in years. That doesn't happen if my starting point is asking how your day is going or how long you've lived in Arlington, Virginia
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(we went to school with a LOT of people who live in Arlington, Virginia)
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There's one conversation that stood out. My old buddy Kevin. Classic college friend you loved but also lost touch with. Saw him for the first time in 25 years and used the Vanessa question about highlights. By the end of the weekend, we were good friends again.
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Afterwards he sent me this text:

Imagine if more of your conversations ended like that.

Last year I helped a longevity doctor with podcast interviews. Know what the number one predictor of a long life is? It’s not exercise or genetics or eating 14 servings of oily fish. It’s strong relationships.

But it is hard to make adult friends. Especially for dudes, who have been socialized to only talk about work and fantasy football.*

Whether it’s speaking on a stage or to a friend, you’re DOA if you go down a predictable path. Problem is, your first instinct is likely to be predictable. We leave charisma on the table when we don’t do the work to make our communication sticky.

Getting past the predictable is what Vanessa’s new book, Conversation, is about. It's one of the reasons I'm so excited to read it**.

Vanessa is one of my oldest internet friends, she pours her heart into everything she does, and I'd love it if you ordered her new book. I don't get any kickback from that link, btw. I just believe in her work. I bet you will too.

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​*The only thing less interesting than talking about fantasy football is talking about fantasy football injuries. Wow, you had Saquon and he got hurt? Freaking fascinating. Let’s be friends.​
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​**Also because I'm on page 115

Speak well, my friends
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Cheers,
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600 1st Ave, Ste 330 PMB 92768, Seattle, WA 98104-2246
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