We all face dilemmas and choices in life: Should I buy these pair of boots? When should I wear these boots? Do I even love him - and more than my boots?
These are a portion of the questions the protagonist in "Are You Ready, Boots?" encounters as she contemplates her life and future.
Lulu is far too independent for this, and while she loves it while they're together, she still has a raunchy side, which she demonstrates on the night she meets Charlie.
Spencer has instilled skepticism in Lulu's head, and she starts to realize something about Charlie that she dislikes – which she avoids until the boots come up. Charlie, as Spencer implied, is predictable, and Lulu can tell that he has plans of proposing to her.