2. Is there any significance to Gillian walking into Maddie’s office on a day that Maddie absolutely looks the worst we have ever seen her?
2. I don't know if it's a significance that Maddie looks like "she's had a rough morning". But maybe that scene is to show the difference between the two women: Maddie expected to get a little help, but she wasn't depending on it - as an independent woman, like she pointed out, she would have appreciated a man's help, but she could do without: fixed her tyre all by herself.
Gillian, on the other hand, did not only need or appreciate David's help, it was more than that: she was decided to use him (and she did).
Excellent point, sandra. Maddie does not want to depend on any man, especially for his money. She wants to stand on her own two feet, whereas Gillian would prefer to prop hers right on a guy's lap and expect a massage. Gillian makes it perfectly clear that she wants the "suite" life and does not want to "work" at anything, including a relationship.
"Lady gets in trouble, it's nice to know she has somebody to call"