M / 28 / Developer in fintech / financially stable / loves travelling / MMA / guitar / badminton / cricket financially stable,socially active — but why do I keep fumbling dates? What am I doing wrong?

I’ve been thinking about this way more than I probably should, but I genuinely want some outside perspective because I’m starting to notice a pattern.
On paper…..I don’t think I’m doing terribly in life. My career is going well, I’m financially stable, I travel quite a bit, I train MMA, play guitar, badminton, cricket, have friends, and generally have a pretty active life.
But when it comes to dating/relationships, I seem to repeatedly end up in the same place:
\*\*I meet someone I genuinely like → I see potential → I start investing emotionally → I overthink everything → I try harder to make things work → I become increasingly aware of whether they’re reciprocating → eventually things don’t work out.\*\*

And after three situations recently, I’m beginning to wonder if \*\*I’m the common denominator and I’m doing something fundamentally wrong.\*\*
I’m not talking about three women rejecting me for exactly the same reason. The circumstances were different. But the \*pattern in my own behaviour\* feels similar.

\*\*The confusing part\*\*

I don’t think I’m that incapable of talking to women or meeting people.
I’m reasonably social. I can hold conversations. I have hobbies, friends, a career, interests, and I’m comfortable meeting new people.
The problem seems to start \*\*after I become genuinely interested in someone.\*\*
That’s when my brain apparently decides to turn dating into a fucking engineering project.
I start thinking:
Did I text too much?
Should I give her space?
Should I initiate?
Is she interested or just being nice?
Was that reply a good sign?
Why did she react to my story but not message me?
Should I ask her out?
Am I moving too slowly?
Am I moving too quickly?
Should I flirt?
Did I make things too friendly?
Did I not create enough attraction?
Should I have been more direct?
Is she busy or losing interest?
Should I stop initiating and see if she comes toward me?
If I stop initiating, will she assume I’m not interested?
It’s fucking exhausting.
And the worst part is that \*\*I know I’m doing it while I’m doing it.\*\*

\*\*I think I have a tendency to over-invest\*\*
When I like someone, I naturally want to put effort in.
I remember things they tell me. I want to make plans. I want to do thoughtful things. I like giving small gifts. I like sharing things I think they’ll enjoy. I want to know them properly rather than just casually dating for the sake of dating.
I don’t think these qualities are inherently bad.
But I’m starting to wonder whether \*\*the timing and amount of investment is wrong.\*\*
Maybe I’m giving someone the emotional investment of a relationship when we’re still at the stage of figuring out whether we even like each other.
And then when the other person doesn’t reciprocate at the same level, instead of taking that as information, my instinct is:
\*\*“Maybe I need to do something differently.”\*\*
So I try harder.
That’s probably not healthy.

\*\*Another thing I’ve noticed\*\*
I seem to focus a lot on \*\*how to make someone interested in me\*\*, instead of asking:
\*\*“Are we actually mutually interested in each other?”\*\*
That’s a subtle difference, but I think it’s huge.
Once I like someone, I start thinking about how to create chemistry, how to keep the conversation interesting, how to flirt without overdoing it, when to ask them out, how frequently to text, etc.
But maybe attraction isn’t something I should be trying to manufacture.
Maybe I should simply show interest and then \*\*watch what they do with it.\*\*

\*\*I also think I sometimes confuse comfort with progress\*\*
If someone is comfortable talking to me, shares things with me, laughs at my jokes, responds positively to thoughtful gestures, tells me personal things, etc., I tend to interpret that as:
\*\*“Okay, there’s something here. I just need to let this develop.”\*\*
And then I become patient.
But eventually I realize that maybe the other person simply \*\*likes me as a person\*\*.
That’s a difficult distinction for me because I don’t want to prematurely walk away from something that could have developed naturally.
At the same time, I don’t want to spend weeks/months trying to turn friendship-level comfort into romantic attraction.

\*\*I think I also have a problem with uncertainty\*\*
When someone is clearly interested, I’m actually pretty relaxed.
But when someone’s interest is ambiguous, I become extremely analytical.
And ironically, that’s probably when I behave the least naturally.
I’m thinking about being natural instead of actually being natural.
I’m thinking:
“What would a confident guy do here?”
Instead of simply thinking:
“What do I actually want to say?”
And I suspect the other person can probably feel that difference.

\*\*There is another uncomfortable possibility\*\*
Maybe I’m simply choosing people who aren’t that interested in me.
And because I like them, I keep trying to overcome that gap.
Maybe I’m subconsciously attracted to the \*\*potential\*\* rather than the reality.
Maybe I’m interpreting small signs of interest as evidence of larger interest because I \*want\* them to mean something.
Maybe I should be looking for someone who is making my life easier rather than someone I constantly have to figure out.

\*\*But then there’s another side of me\*\*
I don’t want to become the guy who plays stupid dating games.
I don’t want to intentionally delay replies.
I don’t want to pretend I’m busy when I’m not.
I don’t want to withhold affection just to create scarcity.
I don’t want to become emotionally unavailable because “that’s what women like.”
If I like someone, \*\*I want to be able to fucking like them.\*\*
I just don’t want to lose myself in that process.
So where is the line between:
\*\*showing genuine interest\*\*
and
\*\*chasing?\*\*
Between:
\*\*being consistent\*\*
and
\*\*over-investing?\*\*
Between:
\*\*being patient\*\*
and
\*\*ignoring a lack of reciprocity?\*\*
Between:
\*\*giving something a chance\*\*
and
\*\*trying to force something that isn’t there?\*\*

\*\*What I’m currently questioning about myself\*\*
Maybe I’m too intense.
Maybe I’m too available.
Maybe I’m not flirtatious enough.
Maybe I wait too long to make things romantic.
Maybe I become too emotionally invested too early.
Maybe I overthink instead of acting.
Maybe I act too much instead of letting things happen.
Maybe I’m trying too hard to be “the good guy” and not enough of myself.
Maybe I’m trying to create a relationship rather than simply seeing whether one develops.
Or maybe I’m overthinking the entire thing and sometimes \*\*two people simply don’t have chemistry\*\*, regardless of how well they seem to align on paper.

\*\*The career/life part makes this even more confusing\*\*
I’m reasonably doing well professionally and financially.
I train MMA.
I have hobbies.
I travel.
I can play guitar.
I play sports.
I’m independent.
So intellectually I know I have a life outside dating.
But when I genuinely like someone, somehow \*\*that person starts occupying way more mental bandwidth than they should.\*\*
And that’s what bothers me.
I don’t want dating to become the thing that determines how I feel about myself.
I don’t want a rejection to make me question whether there’s something fundamentally wrong with me.
But three situations going badly in relatively close succession has made me wonder:
\*\*Am I actually the problem here?\*\*

\*\*So I’m looking for brutally honest advice\*\*
Not:
“Bro, just work on yourself.”
Not:
“The right person will come along.”
Not:
“Women are complicated.”
I want people who have actually recognized this pattern in themselves to tell me what I’m doing wrong.
\*\*What behaviours scream “over-investment” to you?\*\*
\*\*How quickly should romantic escalation happen?\*\*
\*\*How much should I initiate before I step back and let the other person come toward me?\*\*
\*\*How do you distinguish someone being friendly from someone being romantically interested?\*\*
And most importantly:
\*\*If you were in my position, what would you change about the way you date?\*\*
Because I’m starting to realize that maybe the answer isn’t \*\*“try harder.”\*\*
Maybe it’s learning to \*\*invest only after someone shows me they’re investing too.\*\*
And honestly, I’m interested in hearing the uncomfortable answers.
\*\*Tell me where I’m fucking this up.\*\*