Did you ever see Next Stop Wonderland? Long before there were tax breaks bringing Hollywood to Boston to shoot, local director Brad Anderson, filmed this romantic comedy that asked the question, "Do you believe in fate?" I saw this movie at the Kendall Movie House in 1998 and met Brad who did a Q&A after the film concluded.
As you could have guessed from the title of the movie - much of this was filmed along the Blue Line, but there is plenty of Boston to see in the movie. The clip below shows, Erin Castleton - played by Hope Davis, in her apartment in Union Park in the South End recovering from just being dumped by her loser of an x-boyfriend, when her meddling mother calls to let her know that she placed a personal ad in the Boston Herald. Clearly this is a flashback to a time before Match.com, eHarmony, etc... I don't even think that people place personal ads in the paper anymore.
In addition to being a wonderful cult film that shows much of Boston, the movie has a beautiful soundtrack that is Bosa Nova inspired. I have the soundtrack and still play it frequently some ten years later.