<human>: I just had a very long discussion with a girl I (M) find attractive, we have been housemates for about 3 months. Over the holidays we were chatting online discussing all sorts - old schools, board games, posters on our wall. It then moved onto serious stuff like the expectations of society, our diminishing individuality as a result of the pressures on our lives. This lead naturally onto mental illness and stress. She expressed her dissatisfaction with her life and feeling worthless. I empathised with these emotions as we are both of a similar age (20, 21). Of course we both discussed getting professional help if the need arose (personally my mental health is at an acceptable state for now). She continued for a bit with her worries and no-one liking her and the common question of whether her friends actually were her friends. I insisted that I was and chose that moment to express that I found her attractive. The response was one of gratitude. I was not expecting reciprocation considering the circumstances but I was concerned post-conversation that this may have been interpreted as pity when in fact it was genuine or that it was poorly timed considering the subject matter. I am curious of people's opinions. The conversation flowed naturally after that, talking about LOTR and other nerdy stuff. I will be seeing her again in January, suggestions?

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<bot>: Told a girl I liked her after a discussion of her mental instability, was it poorly timed? Should I approach the subject(s) again or just take things naturally?