I've now played a fourth time and managed to marry Bobby this time. This fourth attempt is the first time I was young enough to have my own kid. In this playthrough my mother died before I had Ned (my child) but still the game mechanics say I drop off my kid at my mums house.

I saw him get married but died before I got grandkids. (I adopted a child on my second playthrough and only got to his wedding there too)

There's still work to be done