I'd have to look in the script to make sure, but if it works this way then it makes certain sense -- if Ian ignores opportunities to get things on with girls like Cherry or Lena then he's clearly not yet over Gilian or the effects their breakup had on him :vAnnoying how you can only delete on Lena, Alison, or Cherry routes. Other routes like Holly, Cindy, Emma, Minerva all start later. So Ian doesn't have a will point to spend on deleting the picture.
edit:
okay, i looked in the script and no, that statement isn't accurate: Ian can also gain will point in Ch.2 doing honest book review or review switch with Holly. So he doesn't need to hook up with anyone early to delete the photos in Ch.3
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