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I finished pretty much everything except for Ruby. I seems to be stuck on 'Ask Ruby for a Handjob'. I can't really ask her anything, maybe because I got stuck at 2.75 hearts? Any fix I could do or am I done for and have to start over? Or am I just dumb and can't understand simple quest? 

Show her more love, take her to the bathroom and shower her with attention at school. Don't be rude to her when asking for sexual favors and also if you day after day relive your first time having sex with her you could get her to love you max quickly. Then when studying at her house ask her to give you one at the table and continue trying to convince her, make her swallow though and you'll lose a heart.

It won't let me do anything else tho? It only let me 'imagine her without clothes' and 'end conversation/ say nothing'. That's the only this I could do and the only place I could found her is in the classroom. Her heart meter never changes.