After years of watching kid movies and bad mock-umentaries about boy bands, I introduced my teenage daughter to one of my favourite movies from 1989, featuring my boyfriend John Cusack: Say Anything.

The film tells the story of a two high school seniors – polar opposites in scholastic achievement, popularity and future goals – who fall in love and have to find a way to bridge their worlds at a time when they seem to be falling apart. Sigh. Young love with a great soundtrack (The Replacements? Peter Gabriel? Hello!).

The timing seemed right to pull out this classic film. My daughter had just come through another portal of growing pains fraught with the hard and fast lessons of responsibility, friendship and the all-powerful reminder that we have no choice but to grow up (or at the very least, grow older).

It didn’t help that her life skills class assignment posed the terrifying question: “What do you want to do with your life?” And she didn’t have an answer. Of course she didn’t: she’s 13. But clearly her inability to answer the question made her feel like a failure. Just what every young girl needs: more self-doubt.

I refrained from telling her that very question keeps me awake at night more times than I care to admit. I knew sage advice (borrowed from Oprah) would only land on her headphone-wearing ears, so out of desperation I figured a film about teen angst would be a clever disguise to reassure her that the uncertainty of growing up isn’t new; it’s as old as time, even as old as me.

To use her generation’s words, my efforts were an “epic fail.” Apparently ‘80s films might as well be in black and white with subtitles. She watched with curiosity as teenagers spoke directly to one another in real time, in complete sentences without the use of a mobile device.

One of the movie props was this thing with a long chord stuck in the wall called a telephone and the only way to talk to friends privately was to stretch the curly chord from one room to another.

In one scene, Cusack’s character, Lloyd Dobbler, made a telephone call from inside a glass box using quarters. Freaky. In another scene, the girl used a big, thick book called a dictionary. Nerd.

My daughter wasn’t the least bit impressed when the very question that plagued her was posed to Dobbler and his free-spirited reply was, “What I really want to do with my life – what I want to do for a living – is I want to be with your daughter. I’m good at it” (he meant that line for me, you know).

Every time I hear Peter Gabriel’s song In Your Eyes, I look out the window to see if maybe, just maybe, Cusack is standing on my front lawn in his long, beige coat, his Clash T-shirt and combat boots, holding a boom-box high over his head, declaring his love for me through the lyrics of that song (what? This is my fantasy; let me have it). My daughter couldn’t believe the dude didn’t have an iPod. Lame.

Yes, the generation gap is alive and well, but the answer to that age-old question of what to do with your life remains the same: to be happy.

Now that is a life skill.