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For everyone wondering about this.

If you want to romance Aeolus and do not want to be mean to either him or Esme at one point (there may be a way through doing this as well), this is how it works:

You need to have high reputation with both him and Esme on day 39. With Esme it is at least in the "buddy"-range (numerically above 75 in savegame-editing language). Aeolus should naturally also be very high.

When you enter your room on day 39 and Aeolus greets you with saying that Esme likes Shawn more than him, you get the right dialogue options with him then.

It was a little counter-intuitive for me that you need to be really close to Esme to be able to woo Aeolus, but well. What aren't you going to do for love.
Post edited February 06, 2020 by f_w
You nailed it!

Aeolus is the hardest person to woo for this reason, but yeah that's how you do it.