I’m generally a confident person. I’ll walk into a room of strangers, pitch an idea to investors, or take on a challenge in business without flinching. Give me a problem, I’ll figure it out. Give me an obstacle, I’ll climb over it.
But romance? Romance makes me feel like a complete and utter idiot.
And I proved that to myself again this weekend, with a girl who lives in London.
The Confidence That Vanished
Here’s what makes it so frustrating: I used to be good at this. Or at least, I used to feel like I was.
Somewhere along the way, after a handful of bad experiences that left me more self-conscious than I’d like to admit, I lost whatever social fluency I once had in this area. It just… disappeared. Like a skill I forgot to practice until it atrophied completely.
Now, when it comes to someone I actually like, I become a different person. Not a better version of myself. A more anxious, second-guessing, overthinking version who replays conversations in his head at 2am asking “was that too much?”
The signs are unmistakable:
- Overthinking everything with a single message
- Second-guessing constantly: the moment I press send, I’m already wondering if it was wrong
- Getting physically nervous: we’re talking actual butterflies, dry mouth, the whole thing
- Feeling completely off: Like I’m performing instead of just being myself
And I think I know where it started. A few recent bad experiences, situations where I cared, and it didn’t land the way I hoped, made me more guarded. More cautious. Too focused on the outcome instead of just… being in the moment.
When you start caring too much about whether it works, you stop being present. And people feel that.
The Dating App Disaster (That Wasn’t Even My Idea)
Last night, a friend of mine decided to throw me onto a dating app without much convincing on my part. With good intentions, I’m sure. I said fuck no. She said “just try it.” I said no again. Then, out of some mix of curiosity and social surrender, I let it happen.
I woke up this morning to over a hundred right swipes. In less than ten hours.
My first reaction wasn’t flattery. It was dread.
Fuck no. Absolutely not.
The thought of spinning up a hundred parallel conversations, navigating the same “so what do you do?” exchanges on loop, eventually grinding through dozens of dinner dates, it made me tired just thinking about it.
That’s not how I’m wired. I don’t want a numbers game. I never have.
What I want, and what I’ve always connected with more, is the accidental run-in. The organic moment.
The situation where you meet someone in a setting that has nothing to do with romance, and something just clicks. Like with the girl from London.
That wasn’t engineered. It wasn’t a profile and a swipe. It just happened And those moments are rare, which is exactly why they mean something.
Looking at that app didn’t inspire me. It discouraged me. It felt like the antithesis of everything I actually value in connection.
The Contradiction at the Heart of My Social Awkwardness
Here’s the part I genuinely struggle to explain, even to myself.
On platforms like Tandem, where I interact with people learning languages. I’m apparently popular.
Women in particular seem to gravitate toward conversations with me. And if you asked any of them what I’m like, they’d probably tell you the same thing: I’m respectful, warm, and I keep a clear distance from anything romantic. I’m safe to talk to.
Which sounds like a compliment. And in some ways it is.
But in the context of actually pursuing someone I like? It becomes a problem.
Because here’s the brutal contradiction I live with: I know when I like someone. I know it clearly and immediately. There’s no ambiguity inside my own head.
But the moment I try to communicate that?
I either go full black-or-white. Way too direct, too honest, too “here’s exactly what I’m thinking”, or I freeze and say nothing at all. There is no middle gear. No subtle. No playful ambiguity. No “let me drop a hint and see if she picks it up.”
That’s not me. I don’t do hints. I do honesty.
And while I respect that about myself, I’m also aware that it can come across as intense. Maybe even overwhelming.
Someone you’ve just started getting to know doesn’t necessarily need to feel the full weight of your intentions before you’ve even had a proper conversation. I know this. And yet I can’t seem to stop doing it.
It’s like my internal compass only has two settings: all in, or step back completely. No calibration in between.
And that, more than anything, is what kills me. Because I’m not trying to be too much. I’m just… me. Unfiltered. And sometimes that comes at the wrong time, in the wrong amount, for someone who isn’t ready for it.
The worst part? I don’t always realise it until after. Until the silence gets a little louder, or the replies get a little shorter, and I’m left standing there doing a postmortem on every conversation wondering where it went sideways.
To the Girl from London (If You’re Reading This)
I genuinely hope you are.
Because if you’ve made it this far, you now have more context than most people get in months of knowing me. Some of what I’ve said or shared recently might have felt like too much, too soon.
And you’d be right, it probably was. Not because I was trying to overwhelm you, but because when I feel strongly about someone, I don’t know how to throttle it. The filter breaks.
So if anything landed strangely, I’d rather you understand why than wonder what the hell was going on with me. This is what’s going on with me.
What Comes Next
I don’t have a clean answer here. I’m not going to promise some personal growth arc where I figure all of this out and come back with a triumphant follow-up post.
What I can tell you is what I’m not willing to do.
I’m not going to start chasing attention from every direction just to feel validated. I’m too old for that, and too self-aware to pretend it would make me feel anything but empty.
I’m not going to outsource my love life to an algorithm and a swipe mechanic. And I’m not going to change the fundamental way I show up for people. Honest, direct, all-in, even if it keeps backfiring on me.
What I am going to do is try slowly, imperfectly, to give things room to breathe. To stop gripping outcomes so tightly. To remind myself that the right person won’t be scared off by the fact that I mean what I say.
Because somewhere in all of this awkwardness and overthinking and contradiction, there’s a simple truth I keep coming back to:
I just want one person. Not a roster. Not options. One person I can actually show up for, without the nerves, without the second-guessing.
Hopefully, she’s in London.
Thanks for reading. If any of this resonated, or if you just enjoyed watching someone spiral publicly on the internet, I’ll see you in the next one.