@sakuchu
It's been awhile since I read this, so I decided to re-read the chapter while carefully considering your take on it.
Unfortunately, it still hits all the wrong notes for me, relationship-wise. I'm all for give-and-take, but this chapter has shown me yet again that it was too much give for the FL (change dress style, change her interpersonal approach, change her usual method of efficiently managing things, which is who she really is) and too little take from her crush, who despite all her accommodations, still let the insecurity get the best of him. The ML's "you're not cute" line is also too condescending for me.
For context, I personally am in a relationship (15 years together, marrying him in Spring 2021, yay!) and my personality's similar to the FL. I didn't need to drastically change what makes who I am, and he didn't need to do it for me either. We changed a bit along the way as our perspectives matured, but I'm still mostly the efficient planner (the "mom" as you put it) and he takes care of the unexpected inconveniences that may crop up along the way. At times, the roles shift but we have mostly settled on this familiar, comfortable setup.
No conscious effort of "boosting someone's confidence"--whoever's better at something takes the lead, period.
Thanks for sharing your POV! I always appreciate an opportunity to chat in-depth about shoujo/josei reads. <3