1. The premiere packs a hormone-driven punch as underage Serena van der Woodsen engages in an alcohol-fueled tryst on a hotel bar with her BFF Blair Waldorf’s boyfriend Nate Archibald (season one, episode one).
2. Chaste queen bee Blair tosses aside her virtuous ways and performs a striptease for Chuck at his burlesque nightclub, then succumbs to his charms in the back of his town car (season one, episode seven).
3. On the verge of losing his hotel to Uncle Jack, Chuck offers up girlfriend Blair in exchange, inevitably leading to a breakup. A normal problem for a pair of teens (season three, episode 17).
4. Season three ends with a bang as Chuck Bass lies bleeding from a gunshot wound in a Prague alley, Blair’s engagement ring in hand (season three, episode 22).
5. After a recent transformation into a good girl, Serena is drugged by enemies Jenny, Juliet and Vanessa, then abandoned in a hotel room to overdose alone (season four, episode nine).
Program don’t preach | Four letters transformed youthful series ASAP | Top five OMFG moments in ‘Gossip Girl’ history | Upper East Side stories a feast for Meester | Fans fasten their seatbelts for a sartorial ride