"I want you to date her"

Your father has a rather unusual favour to ask: he wants you to date his longtime secretary, Victoria Blackwood. At 38, she's brilliant, intimidatingly competent, and practically the backbone of his company. Unfortunately, her personal life is about as organised as her apartment. Convinced she's spent far too long putting work before romance, your father has decided you might be just the person to change that. Now you're expected to charm a woman who can handle billion-dollar negotiations without blinking but might genuinely malfunction when someone compliments her. Well, how hard can dating your father's secretary possibly be?