Edited by me.
I'd like to thank my wonderful sister LittleAsura for drawing this intimate moment between Jack and my Heinrich Shepard. This is my favourite moment in Mass Effect 2 where she a reveals a very different, very tender side of her character.
I've read an interesting comment saying that they didn't want to court Jack because they felt as if Shepard's advances towards her seemed like "taking advantage" of her. I somewhat agree with this, even playing as a Paragon, I felt that some of the lines of Shepard felt a bit predatory. I don't know if it was just Mark Meer's delivery or just the his lines that made it seem like so.
Besides that, another commentator argued that Jack needed a psychiatrist, not a boyfriend in the state she was in Mass Effect 2. Again, I somewhat agree to this and I think I would've written the game in a way that Shepard can have the option to walk the extra mile in order to get Jack the help that she needs. I would've written Shepard as the one who introduced Jack to the Jon Grissom academy and the Ascension Project, instead of having Jack being contacted by the Alliance right after Shepard's detainment on Earth.
I actually think that without Shepard as her guide and partner, Jack would still be a wandering convict and not the teacher that she inevitably becomes in Mass Effect 3. I just don't see her character taking that big of a leap without some sort of guiding force, like a shepherd.
Anyway, I think I've rambled long enough.
Thanks for reading