I am sorry, I feel like I am watching Lily’s brother putting on make up than Lily. She needs to sort out the brows and it probably solve 50% of the problem. The fact that she wear black creates a false shadow that made her looks like she has beard.
I am not mocking her appearance, she does look pretty back then, I think is the don’t care attitude.
I also don’t get the impression that rich’s role is very demanding, for Associate Director role in a company, it is usually long hours and a lot of call and hard work. Seems to me that he has a casual 9-5