Personal stylist Sasha Brennan discovers she has an unexpected guest for dinner - her brother’s new best friend and wrestling counterpart, Jack “Crusher” Webb. It’s obvious that Sasha doesn’t approve of her brother’s career choice but she can’t deny the arrogant, tattooed stranger in her kitchen is attractive. Jack questions the validity of Sasha’s job and playing dress up with rich old ladies. He confesses Trent is like a brother to him, since he doesn’t talk to his own family. Sasha receives a call from Northwestern Hospital telling her that Trent is in the ER.
Photographer Devyn Deveroux is stuck in traffic trying to get back to the office of Windy City Scandalous with photos she’s just snapped of two celebrities in a rather intimate rendezvous. She reflects on her career as a paparazzi and her secret affair with the online magazine’s editor, Todd Baker, and wonders what the hell she is doing with her life. Later that night, from Todd’s bed, she sees her pictures on the news and the chaos that is has caused. Dev tries to talk to Todd about her feelings but he thwarts her concerns with physical advances.
Ashleigh Taylor is on her way to see an old friend play with his band at the House of Blues. She’s admittedly nervous since Ryder Jones was her best friend growing up across the street and it’s been almost a decade since they’ve seen each other…and she had a serious crush on him their last two years of high school. Despite one sour memory she’d rather forget, Ash is excited to reconnect with her old friend, and can’t help remember their last night together a decade ago when Ryder was packing up for California and suggested they share one last experience together.