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Everyone has to find their sense of self. You might get lucky and the path to that is easy because you find external examples that match your inner self. The opposite can be true, and there's a shit ton in between, to the side, and stuff that's so unique it's impossible to find external guides.
As part of that, finding comfort and confidence in your expression of masculinity is a big hurdle because you can find conflicting things that end up working on that path.
There's been a lot of progress in both rejecting machismo, and finding ways to still express masculinity in traditional ways, or not finding expression in traditional ways and being free to do so without judgement.
Me? I had the good fortune of being surrounded by peers that were rejecting machismo, and adult role models that allowed me to explore my masculinity freely, with only joking commentary that wasn't supportive.
But you're right. A lot of men, genuinely, don't find their masculinity in line with external emotional expression. I even have trouble with when I'll express myself fully because I just don't trust people. And I know there's times when it is necessary to maintain emotional control until it's safe and useful to loosen that control.
And you're also right that women aren't always open to emotional expression. Some can handle bits of it, but still want illusions about other parts. Luckily, they aren't the majority, and it tends to get better as you age. Past your twenties, most women have had their fill of partners that fake being self contained. And past that, they'll tend to appreciate emotional honesty. It isn't everyone all the time, but that's the trend I've seen.
The key, imo, is in being up front about things. Express your thoughts and feelings early and often with prospective partners and friends. Let it filter out the folks that aren't in that place, and you'll end up with lasting bonds based on mutual respect, mutual support, and the intimacy that brings.
That's the sucky part though; it takes time to build those relationships, and many possibilities along the way will either drop off, or you'll be moved to part from them.
The great part about being a man, seeking for a sense of machinery masculinity and emotional intelligence now is the internet. It really is easy to find like minded men willing to hash things out. They likely won't transition into meat space friends, but that isn't always desirable or useful anyway.
Here's a good thing I've picked up though, based om your experience in men's groups. Work and hobbies are the gateway. A lot of men need to build a connection slowly. I know I do. I prefer in those settings to hang back, listen, and give emotional support. Show empathy, and as trust builds, that mutual exchange starts, for those that can follow that path.
That's one of the biggest benefits of being sensitive to one's own emotions. It gives you a chance to understand others', to connect on that level. It often turns into those men having their first chance to really open up and talk honestly about themselves in their own way. And that's a beautiful fucking thing to see.