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Plus one to the above, and I'll double down on it.
Befriend some of the women. Which ones? The ones you find most attractive. Why? If you make it completely clear you are friend-zoing her utterly at the beginning she'll eventually invite you out with her friends and now you're in a 1-male to x-females situation with a heap of social proof from the start of the evening. There is also an extremely good chance that she is "covertly" setting one of the friends up with you.
The key here is that you're doing this within the context of a group dynamic wherein you can (hopefully, and also necessarily) demonstrate some higher status. It's not about being a wallflower and then awkwardly asking to be friends on the side. Demonstrated status and social proof are the coins of the realm. The problem is when guys try to spend them the same place the make them. This is how, at best, you get into a potentially risky office romance or, at worst, get escorted out of the office by HR and/or security.
In group social proof and status is not, however, easily transferrable. Think of groups as countries with different currencies. It's hard to spend it directly in a group within which you did not build it. Have you ever heard a guy in a bar talking about how he has such-and-such a fancy job or was friends with Johnny WhoDat, the biggest waterbed dealer on the West Side? That's an attempt to currency exchange social proof / status. It fails. What you have in your book club is an exchange agent. She, as a trusted member of multiple groups, can port all of that built up social proof and status you have from the book club out into other groups. In fact, that you arrive at these new groups with such a high endorsement introduction automatically jump starts your relative status within the new group. Go for it.
Where were you fifteen years ago when I needed this advice?
I am frustrated that all of the social and romantic advice that I received from adults as a kid was inscrutable and unquantified and vague normie intuitions that I didn't understand. I always knew I was doing it wrong, but couldn't figure out how or why, and nobody could explain it to me. And only since I discovered rationalist and rationalist adjacent spaces did I start hearing coherent logical explanations that I could use to actually figure out social situations and figure it out. And these are verbal descriptions! It's not just that I'm older and wiser and have learned from experience lessons that cannot be taught by words. If I had heard these words fifteen years ago I would have understood them and been able to adjust my behavior!
And the worst thing is that all the normies probably understand all this already and if you told them this they'd be like "yeah that sounds about right", but when they give their own version of the explanation in their own words it's just incoherent nonsense.
As long as you we're 50+ 15 years ago, this advice is still useful.
"but when they give their own version of the explanation in their own words it's just incoherent nonsense." True. The sad fact of the matter is that both men and women have such little knowledge of courtship and how mate selection works. This is because it used to be embedded in socially approved rituals (think 1960s and earlier ... asking a girl to the sock hop, what "going for a drive" actually meant, the term "going steady" etc. etc.) When those rituals started to disappear through the 80s and 90s as women grew up with more fundamental autonomy, no new rituals replaced them. Fortunately, the underlying truth became a object of study. What's so interesting about real Social Dynamics / Sexyual strategy is how universal it is to all of human civilization post the emergence of agriculturalism and larg(er) scale pastoralism.
I'm getting out of focus here, so suffice it to say - most people have no idea how or why they've ever gotten laid - male or female (though probably women have a bit more front of mind intuition about this in general). That's the reason why you get bad advice.
Nobody gets to opt out of playing status games. It isn't possible. You can choose to play them well and retain integrity. That's the good news. The bad news is that status game sociopaths exist and will blow those with morals and ethics out of the water for some amount of time before their local society decides to exile them. The point there is to not get jaded and enjoy your own life.
This relies on there being a local society. My impression is that a significant cause of the modern destruction of dating and friendships is not just the dissolution of rituals, but also the dissolution of local society. If everyone you know is a friend of a friend of a spouse of a cousin, then there are reputational concerns. The good faith actors can vouch for each other and introduce each other to their friends and therefore recognize each other, while the bad faith actors quickly burn through all their social capital and end up as outcasts. If you have forty trustworthy mutual friends who all know each other, then a viable strategy is to only trust people who are vouched for by other people you already trust, and treat any outsiders with suspicion until they jump through a lot of hoops to prove themselves. But if you're in an atomized society where you've moved into a new city 2 years ago and all of your neighbors are people who have also moved here within the past couple years, each from a different place, that's not an option. The strategy to only trust and befriend people who are vouched for is equivalent to having no friends. You have to lower your standards for reputation, which makes it easier for the sociopaths to blend in. And when they are eventually caught they can just move to a different social circle (in a high population area they don't even need to literally move to a new location), and blend in again because people can't afford to ostracize strangers anymore.
This is accurate if you've made the choice to delegate personal autonomy to the group.
That is the path of most.
Reclaim your autonomy. Determine what you see as fruitful.
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This is a golden sentence to internalise. I remember being perplexed at high school why I got decent attention from girls, some friends got a ton of it and others got none at all. Some guys were obviously unfuckable and they seemed to accept this and made no attempt but many did make attempts only to get ignored or scorned or fuck it up quickly if they ever got a chance. Now when I look back it’s all so painfully obvious. I was just a bit more attractive and emotionally stable that early on I got a reputation as the guy who dated a couple of the pretty nice girls. Things just followed. Meanwhile some got the reputation as the guy who threw a tantrum for being rejected or ignored.
If you don’t know what you are doing (or suddenly change significantly in attractiveness etc) it’s practically impossible to change your standing in a group hierarchy.
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