Lorelai begins giving her careers talk at Stars Hollow High, but it is almost immediately hijacked by students who are more interested in hearing about when she got pregnant with Rory, and whether she regrets it. You get the distinct impression that for these teens, Lorelai has long been a source of fascination (and probably of gossip), and they have been waiting for an opportunity to ask questions about her decision to keep Rory and commit to being a single mother.
Lorelai looks to Debbie Fincher for help, but receives absolutely none – it’s a supervised event organised by the PTA, and yet nobody steps in to ask the students to keep their questions only on the subject of Lorelai’s career, not her personal life. Lorelai could have said something along these lines herself, but she makes an attempt to answer their questions honestly, to show that she’s not ashamed. Unfortunately, she makes a bit of a mess of it – by the end she is very unwisely offering to take them all out for coffee to discuss her life in more depth. Boundaries, Lorelai!
One of the girls asking questions is Riki Lindhome (she’s the one with blonde pigtails), who would play the role of Juliet in later seasons of Gilmore Girls. At that time she had had a small role in Buffy the Vampire Slayer. She later got her big break in Tim Robbins’ hit play, Embedded, and was then cast in her first film role by Clint Eastwood in Million Dollar Baby (2004). She’s gone on to have a successful career in film and television, and performs in a comedy duo called Garfunkel and Oates with Kate Micucci.