Conversing with an old friend

Photo: Pixabay

When you’re reconnecting with someone you haven’t seen in a while — months, years, decades — what do you say? I’m changing the way I make conversation.

There are basically three ways to answer the question “So, how have you been?”


You can start ticking off the accomplishments. Since I am an accomplishment- and goal-oriented person, this has always been my default. (These are examples, not my actual accomplishments.)

“Well, my last book was published in September and I’ve spent the last few months promoting it.”

“My son is applying to colleges. What a lot of work! Yes, he’s aiming at Harvard and MIT — I don’t know what we’ll do if they both say yes.”

“We’ve just finished remodeling the upstairs. It was hell to live through, but at least I can look at my bathroom without feeling queasy any more.”

The challenge, of course, is that when you talk like this, the conversation has nowhere to go. The other person can try to match you. They can ask about your accomplishments, which is fun for you but eventually pretty empty. Or they can shut up and feel inferior. None of that is good for friendship.


Sometimes, things aren’t going so well, so you’re looking for sympathy. So you say stuff like this:

“Well, my Dad died last year and that was pretty rough.”

“Since Helen lost her job it’s been frustrating. The publishing business is tanking.”

“Well, Kristen is in rehab again. It’s so hard when your kids have become adults but just can’t get it together.”

Naturally, your friend’s response to this is to express sympathy and support. So you can spend a little while talking about your personal situation and getting support.

Of course, you can combine the two modes.

“After the stock options vested, we were able to buy a vacation place in the mountains. But then when weren’t there, the pipes froze and the damage was catastrophic. Now we’re fighting the insurance company. It’s a mess, so frustrating and time consuming.”

The challenge with both of these approaches is that they wind down and you don’t end up learning much about what’s really going on with someone. The brags don’t deepen friendships; the whines don’t allow room for much but sympathy (or, sometimes, irrelevant advice).


I have no idea why I never learned to do this; maybe I’ve just been an egotistical ass all my life. But when I get to together with an old friend who I haven’t seen in a while, I’m going to try inviting give-and-take with an open-ended statement or question. Like this:

“Being a freelancer has been an interesting challenge. I love being my own boss, but I hate doing everything myself. And the flow of cash is so uneven. It’s made me think differently about what work actually is.”

“When your kids get older, it’s a challenge. They are their own people, but they’re inevitably going to make bad decisions out of inexperience. When do you step in and when do you hang back? It’s an interesting question.”

“I love to travel, but my knees and my back keep causing problems. I’m wondering where I could have the greatest adventure and still end up comfortable enough to enjoy it.”

After a response like this, my friend and I will both have to think. We will have to actually converse. My friend may actually end up engaging with who I am, what I’m going through, and how I think and feel right now. And it makes it easier for them to open up about what they’re going through. You only have so much time on this earth. This might make it easier to connect with my fellow travelers.

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  1. I like this. I suspect it’s not your wheelhouse, but this strikes me as the seed of an interesting book.

    I find that conversations are always more interesting when I approach them from the perspective of what I can learn. If the other person is genuinely doing that too, it makes for a really great interchange. If only I’m doing it, I learn what I can and check out fast.

    When I’m the one tooting my horn and talking more than really listening, sometimes it works and feels good. Other times no. But the good feeling is always fleeting. Like a high that always leaves you seeking more.

  2. Josh, Thank you for sharing this! I really love your perspective on this, and will be consciously working to implement this advice.

  3. Why not just ask the ‘long time no see’ about his experiences and listen patiently to what he/she wants to tell you, until he/she asks you about ‘what you have done’?

  4. Why not start with a shared memory?
    Do you remember Mrs. X’s class? Well, to my surprise, I’m finally putting it to good use….
    I remember how you always used to tell me about XYZ? Well, it must have made an impression on me, because now, I’m…
    As I recall, you were always an avid reader. A few years ago, I started a blog, and I got bitten by the writing bug…
    In any case, just say a few sentences and then ask about them.