Wildly hilarious and occasionally heartbreaking, The Longest Date is Chupack's account of her failed first marriage to Perfect Man #1 (who, after two years, realised he was gay), meeting Perfect Man #2 (Ian), and their mutual realisation that matrimony is a matter of constant negotiation about cooking, holidays, space, money and sex. Her observations will ring true with women everywhere, and when Chupack recounts their ongoing struggle with infertility even the most hardened reader will be in tears.