@elainechaya has captured my heart. I only discovered her now with her wedding recaps, yet she's continuing to post regarding the divine plan when it comes to bashert.
Under one of her posts, someone left a snide comment about how easy it is for her to talk about divine timing after the fact. Yet it's what I learned too—there was nothing I did that lead to the desired outcome. It's not like that I saw a distinct line between chasing after shadchanim and attending torturous singles events and dabbling with online dating. It was nothing I had done in the name of "hishtadlus," or rather "proving to everyone that I was doing my hishtadlus."
What's difficult about so-called "dating hishtadlus" is that there are no specific parameters to abide by. "Going to shadchanim" doesn't really mean anything, because there are a bazillion shadchanim and going to them all isn't really feasible and who knows if that shadchan actually knows or would even set you up with your bashert?
Same for singles events—I hadn't gone to many, but according to Han, pretty much the same people are at events: the ones who are willing to attend them. So one meets the same people over and over.
"Dating hishtadlus" is not the same as other hishtadlus. Like "making the train hishtadlus." There are clear parameters. Get up early. Dress for the weather. Leave the house on time. If a lightning bolt cracks into a tree which falls across the road and your car is trapped, well, you did your hishtadlus.
But that's not how "dating hishtadlus" is perceived. If one isn't married by a socially acceptable narrow age range you are huffily told you aren't doing "enough." Whatever "enough" is. If you try to invoke some emunah or bitachon you're told you're an idiot—until after you marry.
The only real dating advice is self-improvement. The best way to meet an incredible person is to become an incredible person. — Mark Manson
That's the only real, tangible dating hishtadlus.
I'm not sure I really understand all of what you talked about but I met my husband walking to Shul on Yom Kippur. He saw me across the street and thought to himself -" that's the girl I'm going to marry."..Later a mutual friend introduced us and we were married a year later - that was Bishart!!! I was 19 when we met and felt the same way you did!! Lucky to have found someone already. Many of my friends were engaged at 18..
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