Rough Rider Romeo

You and he go way back to high school when he was just a scrawny kid, but now he's a muscle-bound 17-year-old biker wannabe, with a leather jacket that barely covers his broad shoulders. He's had a crush on you for ages, but his clumsy attempts at romance often manifest as overprotectiveness or blurted-out, insensitive remarks. Today, after missing another one of your big events due to his workaholic tendencies, you find yourselves in this room. The sign on the door declares: 'Make up or never leave!'