It sounds like you would love this book. It's the memoir of Norah Vincent, a 5'11" androgynous lesbian who spent a year living as a man to find out what it was like. Fantastic book.
Are you talking about this book:
I wouldn't call that picture feminine per se. But whatever.
If you are truly curious why not read this book? https://www.amazon.com/Self-Made-Man-Womans-Year-Disguised/dp/0143038702
Self-Made Man: One Woman's Year Disguised as a Man ( https://www.amazon.com/dp/0143038702/ ) has quite a few interesting things to say. Relevant here are the author's observations on dating: she writes that she expected to have a lot of success as a "boyfriend" with her insight into the female mind. That didn't happen -- women picked up on her lack of masculinity and in general weren't happy with it... in person.
But she did experience staggering success in the pre-first-date courtship portion of online dating, allowing her to get dates at rates much superior to what a real man would expect. Online, the women apparently didn't have a good sense of what they wanted.
Your observation reminded me of that -- people preferring a certain approach even though it's actively counterproductive.
You're referring to Self-Made Man , a great book IMO.
I've read that book . It's alright, but I feel like she conflates some of the particulars of her choices with her generalizations about men.
The things she does:
Joins a bowling league. This one is the best. I think she learned the most here. By the end I think she groks male bonding and male friendships. She even stays friends with them after revealing her identity (which she does in most of the sections). She ends up being pretty shocked by the depth of relationships she always assumed were superficial because men don't discuss everything. I feel like she comes closest to being a man here.
Works as a regional door to door salesman. I could not relate to this one and don't know what she was trying to do. I hate that hyper alpha bullshit. It was a shitty job in a misogynistic environment (the women she worked with experienced a lot of sexual harassment). I think she got a glimpse of the boys club mentality, but I don't think she understood the dynamics all that well. I feel like she confused the structure of the job, which reminded me of multi-level marketing schemes with high turnover and high pressure, for a hierarchy in the business world. I don't associate being cutthroat hyper-alpha as being male, though. To me, that's just being a sanctimonious prick and being able to get away with it because nobody wants to confront you about it. I feel like she could have learned a lot more about regular men working a job site in construction or trades. I think her problem was that she has no relevant experience to do any of that. If she wanted the real alpha predator male experience, she'd have to join a biker gang or go to prison, but that's not exactly a good idea.
Dating. This one was a bit bizarre. She talks about getting shot down a lot more than she thought, and about how difficult women make it to approach them. I remember her being really surprised with how rude women were to her. I don't think she understood how hurtful it is when you get shut down hard. Once she's on the dates with them, it's not that different from what she's used to, but she says that she doesn't feel any appreciation from women for much longer than she's used to for the effort she puts in. She says that the women, like, blatantly try to manipulate her with sex or affection or attention in very ham-handed ways. She is a lesbian, so she's had experience dating women before, so I think it surprised her how women behave dating men. She also seems a little surprised when she finds that hetero women genuinely seem to like men. They're honestly not looking for women in the body of men. Going in as a lesbian I can understand why she might point it out as being a bit surprising. She eventually has a short sexual relationship with one of the women (after she's revealed her identity, obviously) but by that point it has basically lost all relevance to her purpose.
Going to a strip club. She used this to try to understand male sexuality, but all she did was talk about how disgusting they were and how it harms everybody and not just the women. Personally, I hate strip clubs, but I feel like she didn't get it. Her takeaway was that strip clubs exploit men as much as they exploit women, but, again, I don't feel like she came close at all to understanding male sexuality. I mean, she says she explicitly goes to the worst places she can find, and then she's surprised by how shitty the people are. I feel like her bias came through here more than anywhere else, and she didn't try to understand men here. She just tried to copy the experience. Without the hormones to back it up, I don't feel like this was a particularly informative thing to do. She genuinely sympathizes for the men there, but I don't think she empathizes with them in any real way.
Joined a cloistered monastery. This kind of pissed me off because the whole thing was done under false pretenses so it wasted the monastery's time, and it's not an experience that very many men will relate to. Her takeaway was that men who sacrifice their social lives have a lot of emotional pain. Well, no shit. By this point I think she was experiencing a lot of problems with her own identity, and gets her emotions confused with her relationship with her mentor and friend.
Joined a weird anger management or self help support club... thing. Basically they go on a camping retreat, but it's like 30 guys so it was pretty strange. I had a hard time relating to this one, too, because I have no anger problems and because I'm very self-aware, and nobody in this group seemed to have a lick of self-awareness. She was shocked that a group of men who have no therapeutic guide and have an obvious history of difficulty expressing themselves have difficulty expressing their emotions. By this point she had done all this too long, and the stress had really gotten to her and she starts to crack. She builds this fantasy that they're going to discover she's a woman, kill her in the woods, and hide her body. This whole event came across as very confused and actually kind of creepy because of her fantasy. I can't remember if she actually took a psychoactive drug on this retreat or if she just felt like she did. Either way, she got pretty loopy.
Overall, #1 and #3 were great, but the rest were poorly thought out, poorly planned, poorly executed, or otherwise poorly done. Her anecdotes about walking down the street and how she has to act to pass as a man are interesting. She talks about wanting to experience what it's like to have all the social power, and then is shocked when she finds she suddenly finds a huge number of restrictions on male behavior. How the only emotions you're allowed to express are laughter and anger, etc. I think she honestly thought being a man would be a free ticket to do whatever she wanted and wouldn't be judged by society because... patriarchy I guess? I don't remember her ever using that word, but I feel like that's what she driving at. Overall, she seems surprised by the fact that men are human beings and actually not made of stone on the inside. Given her starting point, that's not that unfair as a revealing conclusion, but it's not exactly earth-shattering, either.
At the end of the 18 months, she basically has a breakdown of some kind. She said she checked in to a mental hospital for awhile. Apparently she was losing her grasp on her own identity. The stress of pretending to be someone else for such a long time just undermined her. She used her time in the mental hospitals as material for her followup book.
In no particular order
A Short History of Nearly Everything - Bill Bryson
Bad Science - Ben Goldacre
Stranger in a Strange Land (Remembering Tomorrow) - Robert A. Heinlein
The Entertainment Economy: How Mega Media Forces Are Transforming Our Lives - Michael Wolf
Self-Made Man: One Woman's Year Disguised As A Man - Norah Vincent
Brave New World - Aldous Huxley
Your Erroneous Zones: Step-by-Step Advice for Escaping the Trap of Negative Thinking and Taking Control of Your Life - Wayne W. Dyer
Games People Play: The Basic Handbook of Transactional Analysis - Eric Berne
Animal Farm - George Orwell
1984 - George Orwell
Freakonomics: A Rogue Economist Explores the Hidden Side of Everything - Steven D. Levitt and Stephen J. Dubner
The 48 Laws of Power - Robert Greene
The Art of War - Sun Tzu
The Book of Five Rings - Miyamoto Musashi
Siddhartha - Herman Hesse
Zen and the Art of Motorcycle Maintenance: An Inquiry Into Values - Robert M. Pirsig
Sophie's World: A Novel About the History of Philosophy - Jostein Gaarder
The Shock Doctrine: The Rise of Disaster Capitalism - Naomi Klein
Bonfire of the Brands - Neil Boorman
Tao of Pooh & the Te of Piglet - Benjamin Hoff
The God Delusion - Richard Dawkins
God is Not Great: How Religion Poisons Everything - Christopher Hitchens
The Naked Ape: A Zoologist's Study of the Human Animal - Desmond Morris
What Every BODY is Saying: An Ex-FBI Agent's Guide to Speed-Reading People - Joe Navarro
Meditations - Marcus Aurelius
The Prince - Niccolò Machiavelli
I'll stop for now, if you want any more message me.