I have related this story a few times on this board but here goes...
My girlfriend (now my wife) expressed an interest in watching with me. I thought really hard about the best episode and showed her Tapestry
. She was unimpressed - no investment in the characters you see. Then I was watching Justice
on a re-run, widely regarded as one of TNG's worse, she loved it; its campness, the naked guys and Picards great end-of-episode-monologue. She was hooked in.
Just goes to show that it will happen when/if they want it to happen. Don't over-analyse.