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Outside of work and places like that there's no issue expressing interest in a girl, in fact it's good to make it obvious by talking to her a lot and asking for her Instagram or telling her you want to take her out for a drink (after you've talked with her a while and noticed some chemistry). Best to set the tone early as it's hard to shift from the background of her mind to the foreground. Normal rules of confidence apply and you should talk to her directly, in fact talk to her friends and your friends and show that you can command people's attention for a while without shrinking away in fear. You mention being isolated, I think improving your normal conversational skills even with male friends will help a lot here. It's a good thing to pursue in general and I think much of dating despair is compounded by general social despair. Dating is just good conversation (which is a skill) + some well-timed moves that display your intentions for more.
As for being creepy.. while expressing interest is normal, there is an issue with prematurely expressing a desire for commitment with a girl, you should set constraints on this in your own mind and even explicitly (twice I have said let's just have one drink and if there's no chemistry we'll leave it there, those dates went well) and treat each date as something that's fun for its own sake with no harm done if it ends. Be ready to pursue a bit but if you're putting in all the effort just forget about her. Don't make the mistake of idealising her, it's fine to kick yourself for blowing your chance with that super hot girl for a bit or be excited about seeing her again but remind yourself that you barely know her. I will say the obvious and don't make any crude sexual comments either, I know some guys can make this work but you don't need to take that risk.
So about talking to girls, all the rules of normal good conversation apply and you can talk about history or whatever, the only difference is you're going to arrange for another meeting down the line (whether that's setting a date or you and her grabbing a drink right then and there). Dating advice which complicates things isn't usually useful in my opinion but keeping the simple roadmap in your head is helpful: set a date (you pick what, when and where or else it'll never happen), meet and talk, try get some physical chemistry going (can be as simple as sitting beside her rather than across from her), make some positive comments about her appearance (not crude but still direct, you show confidence by being direct about being attracted to her), then if she has responded positively to all of that take your shot and go in for the kiss. There will nearly always be some doubt about the right moment for the last bit but sometimes you'll get lucky and she'll say something like "when are you going to kiss me?".
On dating apps, don't spend too much time talking back and forth without setting a date. Unless the conversation is really enticing for both of you (which can happen, I've discussed books and sent excerpts before a successful date) it will fizzle out if you don't set a time and a place. If she cancels multiple times or doesn't respond she probably wasn't going to meet up with you in the first place.
On authenticity, I think there's reason for optimism here. I have honestly gotten my best success with dating when being authentic and specifically finding women I can talk to as an equal in conversation i.e. I don't have to dumb myself down and they surprise me with their wit. Authenticity is polarising, you'll narrow the set of people who you can attract but trade it for greatly deepening the attraction of those you do.
On hoops, there are hoops that you insert yourself (pointless in my opinion unless you suspect a red flag and want to test for it), and there are the hoops which are inherent to dating. The latter I think should just be accepted. Think of it like a dance, you might have a lot of wiggle room to do things your own way but the date isn't going anywhere unless you move on to the next step. The fact that there are traditional expectations on the male is something you should be grateful for as they line the complicated world of attraction with a few obvious signposts for what works.
Even in those, there's no ethical issue. I even know several real life examples where a supervisor dated and married a supervisee, to the benefit of all concerned.
There are logistic and legal considerations, so I'd be a bit more cautious than the usual case. But (aside from the supervisor/supervisee situation) even that consideration isn't likely to blow up in your face, and even less likely to be career ending.
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