It was a LONG time ago but I was never able to pull that off (conforming to what was expected). No matter how hard I tried, I just came off as "odd", sort of 'neither one nor the other', and the more I tried the worse it got. By my late teens, even in boy's clothes and with short hair I would hear whispers "Is that a boy or a girl?" and, after a few minutes "That's a GIRL!" Sheesh! I took an awful lot of abuse from my family for not conforming but I simply couldn't do it.
On the topic of love, I couldn't do that either - I simply wasn't attracted to girls that way, even when they would throw themselves at me. How could I "love" someone if they didn't see me for who I was? I couldn't. Love is about someone loving who you ARE, not who you are pretending to be. I always knew I couldn't do anything about it because I would have to transition at some point or end up dead and I couldn't even think about doing that to some poor girl. There was more than one guy who fell in love with me before transition but I couldn't do that either.
I have known love since transition, a couple of times, and also spent a LOT of time alone but at least whatever happens now is honest.