Once you have bought the maid outfit, there are 3 special events that happen. As far as I can tell, they all only happen once and you don't get the opportunity to repeat them.I've tried skipping quite a few weeks to get it to appear. This was a long time ago in terms of real life, I've seen all of Lucy's events I'm pretty sure, bought all her outfits, etc. I've tried to get the event to replay but have not had it happen, leading me to think it only plays once?
Saturday #1 after buying the maid outfit, you get the opportunity to spy on Lucy when changing.
Saturday #2 - Special event (1) Lucy runs you a bath.
Saturday #3 - Special event (2) Broken vase
Saturday #4 - Special event (3) Bad coffee/ Lucy and the Apron (only happens if you have bought the apron).
Saturday #5+ - Get to choose if she wears own clothes/ school uniform/ maid outfit/ apron.
So unfortunately, yes - it would appear you'll be locked out of the new scene where Lucy gossips about your size with her friends.
It would be good if there was a way of getting the special events to repeat if you don't select the "correct" choice the first time. E.g. maybe you could buy a new bath towel /another vase/ fancy coffee in the online shop and get the action to repeat. Or speak to her on Friday afternoon and say you'll want her to prepare a bath/ dust/ make breakfast the following day.
I believe that Altos is also intending to enhance the cheat menu in the next version of the game, so there might be some options there.