Looks like new Ashley storyline from 0.9.0 has some bugs.
If you give her Madison diary, as part of start of blackmail path (give phone, give diary), and then continue with path to prank Ashley (give phone to Madison, without commenting on pictures), then you will have issue after giving towel to Ashley.
She will comment that you like her, because you already gave her diary (new unvoiced dialogue), but after that, nothing will happen. Story will not progress, and no new dialogue.
.
Additionally, since 0.9.0 added option to get Madison phone back, in that case it is not possible to give phone to Ashley (after commenting she looks like Madison), to start blackmail path.
.
And compliment to Ashley regarding Frank seem to fail now all the time, not only for low romance.
If you give her Madison diary, as part of start of blackmail path (give phone, give diary), and then continue with path to prank Ashley (give phone to Madison, without commenting on pictures), then you will have issue after giving towel to Ashley.
She will comment that you like her, because you already gave her diary (new unvoiced dialogue), but after that, nothing will happen. Story will not progress, and no new dialogue.
.
Additionally, since 0.9.0 added option to get Madison phone back, in that case it is not possible to give phone to Ashley (after commenting she looks like Madison), to start blackmail path.
.
And compliment to Ashley regarding Frank seem to fail now all the time, not only for low romance.