Overthinking and Underdating: Confessions of a Socially Awkward Single Man

If I ever get to write a movie with an auto fictional character in a Bollywood romcom, I’ve got a goldmine of material for the most confused-and-lost-and-thinks-more-does-less perpetually-single character ever. 

I’m that guy who loves his own company so much that I go everywhere alone—art galleries, cinema, coffee shops, even concerts. I don’t need company when I plan. 

But here’s the self-constructed problem when you’re a single person at a social event. There’s always a part of you that goes: 

“Fuck the apps, I want to meet the love of my life or whatever through organic means. So maybe this is it. Maybe I should strike up a conversation with someone I find attractive. Then maybe we get along, and then maybe…”

…and so on.

But it’s all fantasy. I keep reminding myself, “You’re here for the event—enjoy the fucking event!”

And then, gosh, if I spot an attractive woman, my otherwise racing mind freezes in a perpetual state of overthinking. 

“Bhai, she’s here to watch a movie. Don’t be that fuckall creep who tries to make a move. Isn’t this exactly why women feel creeped out in social situations? It’s all minds like yours that can’t let women have their moments of joy. Do you even know what mindset she’s in? What if you destroy her evening by saying hi?” 

And on and on it goes.

Take, for instance, this one time at an event when my eyes caught with this woman, clearly in her thirties. Our eyes kept exchanging looks at least three times until we had that intense four-second stare. Which is too short to mean anything, but too long for a casual glance—like this weirdly charged sexual tension, a dormant bomb ready to explode.

And then, my paralysis kicked in. I did nothing and ended up collecting material for my auto-fiction.

So there we have it. I don’t approach women because I’m… socially awkward? (Or coward?)

Fast forward to a few weeks ago: I went to a music gig in Bombay. I arrived early, standing by in my green linen shirt, black linen trousers, and my prized Parisian beret.

Suddenly, this young woman walks up to me from the middle of the crowd and asks, “Are you some famous musician?”

“No,” I say, still trying to figure out what’s happening.

“An artist maybe?”

“Umm, no.”

“So what do you do?”

I debate with myself for a few heavy seconds. Should I utter that pretentious-sounding W-word? My inner voice says “Go for it,” and so my outer voice blurts: “I’m a writer!”

“Ah. So is there something you’ve written that I might have read?”

And again, I went into this overthinking zone: 

“What’s really going on here? Is she trying to place my face? Is she bored and wants to chat? Or is she good at exactly what I suck at—walking up to a stranger of the opposite sex and hitting it off?”

After a three-second mental calculation, I muttered: “Not sure. I’m a journalist. And I also write for a brand and I…”

Yes, I just couldn’t describe who I am and what I do. Which, again, is so typical of me, as I’ve been grappling with this introduction identity crisis for years. It’s simple to understand: I don’t like labels, and I don’t tell half-truths.

And because labels only reveal half-truths, I feel like a con artist if I introduce myself as a writer or a journalist or whatever. It doesn’t mean much without context. And since I’m often not in the mood to explain, preferring to talk about interesting things in life rather than what I do, I end up botching the intro. I just can’t help it.

So because of this ingrained deficiency (and my inability to read the room) this woman and I ended up participating in the most boring two-minute intros and then tata goodbye.

I’d later take this case to the newly added member of my romantic advisory council who gave me an earful. 

“Listen, my friend,” she said. “You have to take this shit seriously. By the sound of it, she was interested. Nobody calls you an artist in the middle of a concert. And why can’t you just tell people you’re a serious journalist? We love serious writers!” 

As someone who probably falls in the 35th to 55th percentile of conventional attractiveness—a range I have settled on without any mathematical rigour—I am theoretically not supposed to get attention from the opposite sex.

But one thing changes the game: a dance floor with music.

Because—and in the nicest thing I will write about myself on this blog—I am a vibe on the dance floor. Meet me there and you’ll know. I have years of data, from house parties at friend’s places or a sangeet gathering in family, Samarth at a dance floor is fun. 

My limited set of moves know how to groove, and because I really enjoy dancing, I have zero self consciousness, and I can lose myself in the mood. And the women do notice. And I always—always—screw possibilities.

I can’t assume that everyone knows the intricate details of dance floor comms, so first, a short primer. Three physical cues exist to express ambiguous interest on the dance floor. One, give each other more attention in the group when you are vibing. Two, get a little closer on the dance floor geography. And third, hold hands and dance together.

I nail it at step one. I get attention. And my male ego is boosted. Even a hint of romantic potential sends my dopamine levels soaring. But that top-funnel expansion? It leads to nothing because… I do nothing.

Even if a woman would walk up and say “you’ve got some moves” in a flirty tone (as they have), I’d blush and just continue dancing. How do I really respond because I can’t return the compliment if I am not a fan of her moves. So once again, we will do those boring intros, then my socially-awkward personality would kick in, I would smile and then let things go. 

It happened most recently at the same music gig evening. A wordless encounter unfolded—no certainties, but something definitely happened. 

This woman—second woman—has also come alone. When the concert starts, she, just like me, comes right at the front to bang her head (to music). 

There are two people between us. They go away an hour later, leaving a two-person physical gap. She looks at me and I pretend not looking at her. She offers me a cue with that subtle smile-but-not-really-smile—an ambiguous inviting acknowledgement. 

I am confused about how to return the ambiguity—what diameter of the smile is acceptable?—and stay in my position. She comes a little closer. I am still focused on the music (Ankur Tewari genius! Damn good!) and my moves (okayish on that day). And because neither of this is a cognitively heavy activity, part of my brain goes in the analysis zone: is she moving closer because more space is available or is she sending a signal? 

I assume it has nothing to do with me. She again gives me that partial smile. Our hands have an accidental contact. Everyone is in the mood. Shaam suhani. But no, numbness follows. End of story. 

If you think my dance floor disasters are bad, let me take you to a bookshop in Delhi where I truly outdid myself.

I walk into a Vasant Vihar bookshop. She’s already there. No one else is around. I came to buy a book—yes, I had a purpose—but then I see this attractive woman. Suddenly, there’s an extra thing to deal with in my head beyond just finding the book I came for.

The brain wonders: Will something happen here? I mean… how many of us book nerds have fantasised about finding a lover in a bookshop? The romance starting when two hands meet while reaching for books in the same section? It’s dreamy—and here, the possibility of a dream begins to unfold.

But I have a great excuse why I am helpless. She is wearing AirPods, which I read as a sign of disinterest: don’t fucking disturb me.

So I go to the classics section to browse literature from French existentialists. As I’m hunting for Camus and Sartre, I’m occasionally glancing around to see what she’s up to. A few minutes later, I realise the AirPods are now off, and she’s not very far from my shelf.

“What are you looking for?” I thought I’d ask and strike up a conversation. But you now know, I wouldn’t. And I didn’t. More minutes pass as I continue to pretend that I’m solely focused on finding my book. Only to find out that she comes and asks.

“I’m looking for a book to gift to a friend. Can you help me?” she says.

Of course, I would help—what better question to ask a book nerd? After a brief chat about her friend’s tastes, I confidently recommend a new literary fiction, which she accepts without hesitation.

Then she asks if I live around. “No, my parents’ house is in Pitam Pura,” I say, which for some reason impresses her? Because she says, “You come all the way from that part of the town to find a book, and I live around and didn’t even know about this store!?”

After my now-clichéd explanation on how Pitam Pura doesn’t have bookshops and why I like the Priya Market in Vasant Vihar so much, I ask if she likes coffee. Turns out she’s a hot chocolate person. I ask about her plans for the evening, and she says she’s going to her friend’s place—the one she bought the book for. She tells me her name—which I’ve now forgotten—smiles, and says “See you around!” 

All of this happens in around ten minutes, and all through I’m wondering if I could maybe ask for her number. Or maybe just Instagram. Something. But… I don’t. And I’m not saying this with pride. (I’m crying. How do you kill a fantasy?)

Only after she goes away do I realise that maybe I should have really asked for her contact. So I go down and creepily take rounds of the Priya Market complex, hoping I might accidentally create a situation to find her again and exchange numbers. I couldn’t.

At the peak of my self-loathing, in a moment of extreme ridiculousness, I go back to the bookshop and ask the store manager if I can get the contact of the lady who was with me at the store. He gives me a weird look—as he should—and then I make up some fake story. I tell him to give her my visiting card when she’s next at the store (she had ordered a book for herself which wasn’t available that day).

Of course, nothing happened ever since. Except me getting to document this story.

I’m 31 and I still haven’t found a way to get over this social awkwardness around women I randomly meet. I can’t for the life of me flirt—I just can’t. It’s like I’m stuck in some bizarre rom-com where the lead actor forgot to read the script on how to actually rom.

With this self-awareness and patterns of repeated embarrassment comes the paradox: men like me often complain about how hard it is to approach women. But if you’ve read this far, you’ve seen what’s really happening: even when a woman makes the effort, takes the first step, or gives some sign—we (or many like me) still don’t do anything. And then we cry about our singledom. (WTF is wrong, dude?)

So the next time you see a man like me complaining about being perpetually single, remember—it’s probably not the universe conspiring against us. It’s not the apps. It’s not even the ever-elusive ‘perfect moment’. It’s just us—standing in our own way, overthinking ourselves into a corner of missed connections, collecting material for the world’s most frustrating autobiography.