It would have been quite acceptable for CW to write to Anne once he had made some money, because that would have been considered as an official second proposal of marriage (this time by letter). Whether her reply was yes or no, it *would* have been quite acceptable. What would *not* have been acceptable was for an UNengaged couple to write back and forth, with "How are you doing?" and "Any developments in making your fortune?" and "Let me explain what I *really* meant" type of letters! CW need not have tried communicating with Anne via LR or her father - he could have written to her directly in 1808, no problem.