Would it be wrong if I legally changed my gender to female in order to get free drinks and cover waived on “ladies night”?
Setting aside the “right vs wrong” aspect of this, let’s talk about the logistics of this idea. Bear in mind that I’m writing from the perspective of being a citizen of the United States — other countries have different processes.
In order to get the legal system to recognize you as being a different sex, you must obtain a letter from a doctor indicating that you have completed your transition to living as that sex. Most doctor (the ones who are willing to write those letters, at least) follow the WPATH Standards of Care, which require you to live full-time in your proclaimed gender for at least a year – at home, at work, socially… everywhere and at all times. For most people who undertake this process, this means hormone therapy; in your case, suppressing your testosterone production through either anti-androgens or by having an orchiectomy — castration, and at the same time, taking estrogen in sufficient quantity to feminize your body — reduce your body hair, lose muscle mass, grow breasts. You’ll be expected to live as a woman socially – to use appropriate pronouns, and possibly change your name. Oh and to strengthen your case, you’ll need to visit a psychologist and be diagnosed with Gender Dysphoria, which for anyone who hasn’t experienced it, is mystifying at best.
And you’d better get started ASAP – the current administration is stripping away the ability for transgender people (you do realize that’s what you’ll be, right?) to be legally recognized and to be able to access all the rights that you currently enjoy as a cisgender male. Before much longer, any store you visit will legally be allowed to refuse service to you solely on the basis that you’re not living as the gender you were assigned at birth, and even doctors and hospitals will be allowed to stand idly by and let you die from unrelated conditions just because they have an objection to you being transgender.
But dammit, you’ll have successfully avoided cover charges and get drinks for free, right?! It’s totally worth it! Isn’t it?
Or maybe just recognize that being transgender isn’t something to make light of. And pay for your own damn drinks – as someone else pointed out – it will cost you a whole lot less money.