Im stuck on the part where you gotta hook up Elliot with Shana, can someone..

You are probably making the same mistake(s) I made. Firstly you MUST prepare before meeting her. Also when you have the four options about which of her features elliot likes best he mishears you so you should account for that.

If you gave him a compliment for her hair (which I always do- it is like woven silk) then tell him to comment on her freckles as he mishears it as fred curls and associates curls with hair. I think hair gets misheard as wear, style gets misheard as beguile (her eyes) and if those two are correct then eyes must end up being freckles.

When you are first talking to her tell her you have been meaning to talk to her and when she asks about being in your income bracket let elliot continue. He makes a fiscal joke to which she asks him if he's aware how sad he is tell her it is sad he doesn't know more people like her.

Finally he has a sensitive heart to offer her and when she says about looking for it more often tell her that you have it easier as her heart is easier to see. Sorry I don't have any advice about the "our love is destiny, I'll do whatever it takes" etc. I hope the advice I did have helped.