On Becoming a More Interesting Person

Gaurav Kulkarni
4 min readFeb 10, 2015

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Anyone who’s spent any amount of time with me is probably familiar with awkward silence. I’m full of those. It’s a terrifying feeling — sitting across from a person and desperately searching for something, anything, to say. I know there has to be something interesting I can share, but words fail me. So I sit in silence, feeling the distance between me and this other person widen, accompanied by a sense of sad hopelessness. This sense that this could’ve been the start of a great friendship or perhaps more, if only I didn’t have this shortcoming. This inability to converse. My highly debatable conclusion for that internal emptiness I feel when I have nothing valuable to contribute to a conversation was that I was simply uninteresting.

It made sense. When I thought of the people in my life who fascinated me. My friends who felt passionately alive and had enough energy to go around would share the most incredible stories. They would take me from wide eyed to laughing, guiding me through an ocean of intrigue. And it made no matter what the conversation was beforehand, they always had something witty or interesting to say. They made me feel comfortable with my silence because they’d provide enough conversation for the two of us. I wanted to be like that — I still want that. But it certainly didn’t come naturally to me, I would have to learn. So I began a sort of investigation to understand why I fell so short of this ideal I had.

Doing More Stuff

A fairly reasonable first stab at the source of this problem was that I’m not doing enough interesting or funny things in my life. If I was “living more,” I’d never be at a loss of interesting things to say or share. The friends in my life that I looked up to always had an anecdote to share. When someone asks me what I did today, my response is usually, “Uh, I don’t know? Work?”

So I actually spent some time “doing more stuff.” I’d push myself to get out of the house. Wander around, go to classes, read books. I learned to play the guitar because I thought it would magically make me more interesting (it didn’t). In fact none of these things made me particularly interesting.

“Oh yea, I totally went to this dance class yesterday!”
“Yea? How was that?”
“I was a lot of fun, but so tiring.”
“Nice.”
“…”
<silence>
“…”
<crap>

Ok, so just doing more stuff clearly isn’t the key to being interesting and capable of carrying conversation. Back to the drawing board.

Learning From Success

I have a bad habit of only seeing my failures but never my successes. So while I internally feel like I’m a terrible conversationalist with every person I meet, there are a handful of people where this isn’t actually an issue at all. I’ve certainly had people enter my life who could talk with me for days or weeks without either of us ever getting bored. It was something I never really thought about, it was just something that happened.

I spent roughly 9 months in a long distance relationship for most of 2013 and an interesting aspect of that relationship was that I had something I was burning to share roughly 2–3 times a day. Now, over the course of a week, if even one thing happens to me that seems worth sharing, it’s a pretty big deal to me. But if you asked me to really think about how differently I’m living my life now vs. then I couldn’t really give you an answer; not much has changed. So “having things to share” seems a lot less correlated to “what I’ve been doing” and more correlated with “who I’m talking to”.

Another interesting takeaway from really thinking about these different relationships was that I actually felt like I was doing more in my life when I was in this long distance relationship. The mere act of sharing these incredibly mundane details of my life meant my days felt less routine and boring and I actually enjoyed my life more. Again, I wasn’t actually doing anything differently, I was just a lot more excited about the small details that made each day unique, if only to be able share these little details with a significant other.

Lowering the Barrier for Sharing

If I feel like over the course of a week, I experienced nothing worth sharing, maybe it’s not that I’m not doing interesting things, but rather that my barrier for sharing is too high. It turns out most things people talk about aren’t life changing observations or great epiphanies, but rather pretty trivial moments of their life. I’m starting to believe that intimacy is not so much about being comfortable sharing your deepest, most profound feelings, but rather your most mundane. Who would you tell about that weirdly alcohol cake at work, or that adorable old couple you saw holding hands? I definitely feel the loneliest when I don’t feel comfortable sharing these vignettes with any one.

This is very much a work in progress for me. I have to actively push back the voices in my head that tell me, “No one cares, Gaurav”. I want to share myself with you more, because only when I share more of myself do I feel like I’m someone worth talking about. It’s a bit cyclic that way. It was actually one of the largest motivations for me to start these weekly blog posts. So thank you for going on this journey with me.

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