It seems like Ben did want to marry Olivia but her feelings towards him cooled after their relationship dragged on for over a decade. Maybe she had already met Laurence Dobiesz by then. From what we were told Ben waited too long to commit which is one of the self-sabotaging patterns that he keeps repeating. Anna was the rebound GF right after his painful split from Olivia, those rarely work out. She was both well-bred and pretty but while he was clearly attracted to her I heard that they broke up over a prenup. Her moderately wealthy family may have thought that Ben was marrying up despite him being the one doing them a favor. Typical Peerage snobbery…