Old Friends and Public Transport

A new job and a new city. Living on your own for the first time is a brand new experience for James, and after only being alone in the new city for a couple of days he runs into an old family friend. An old family friend who he always had a thing for, and she’s recently single! (She was also his mom’s best friend for years) So what's the best way to get in good with her? Well obviously have some kind of relationship with everyone in her social and family circle in the city is sure to work, right? ....Right?