The problem that I see is that the last people in the world capable or worthy of teaching her this are Connie and Elly. As I've said before, Elly remembers her teenaged years slightly more clearly than John does his but tends to draw the wrong lessons from them. What's more, she still has that annoying habit of not seeing any perspective not immediately her own and is thus baffled when Molly doesn't act like a blase thirty-five year old casually flushing a non-productive relationship. This means that she's going to witlessly alienate someone she's trying to help and leave her with the impression that she's a mean old witch who hates love.
To make things worse, we have to contend with Connie's being a God-damned hypocrite when she bleats that Molly is too young to know what love is. This is because the only reason she moved to Thunder Bay and back is that she couldn't BEAR the humiliation of seeing two flushable drones she could do without with other women so it's hard to sympathize with her when she says that. Factor in the rest of her screwiness and her default belief that Molly is only pretending to have feelings to hurt her and make her feel bad and it's not hard to see why the girl with the rat tail would sooner chill with Genghis Khan than her.