Acclaimed female screenwriter Ivy Ho’s second sally of taking the director chair， CROSSING HENNESSY is an indigenous rom-com pairs Hong Kong’s“God of Songs” Jacky Cheung with a mainland parvenu Tang Wei， actually， this feature marks the long-awaited follow-up of Tang’s incandescent debut in Ang Lee’s LUST， CAUTION （2007） after the film prompted a ban of her in filmng in mainland China due to its scandalous erotic charge， from which Ms. Tang is shrewd enough to find a loop to circumnavigate by being granted a Hong Kong citizenship and also ventures in a South Korean picture LATE AUTUMN （2010） directed by Kim Tae-yong and the pair would tie the knot in 2014.
In CROSSING HENNESSY， it is all start with a blind date. Loy （Jacky Cheung） is a forty-something neer-do-well， cosseted by his widow mother （Paw） who presides over an electronic appliance shop with street smart， and his spinster auntie （Chu） who ministers to his quotidian requirements， no wonder he is perpetually stuck in arresting development， only the tidings of his ex-girlfriend Man-yu （Maggie Ho-yee Cheung） can jolt him out of lassitude. On the other end of Hennessy street in Wan Chai District， Oi-lin （Tang） is a parentless young woman works in her uncles bathroom appliance store， she already has a boyfriend Xu （On） who is presently cooped up for his hoover act， considerably， her uncle （Lam） disapproves of this relationship， so in the first place， both Loy and Oi-lin agree to the date only to appease their elders， and in the presence of these eager-beaver matchmakers， there is not a scintilla of spark occasioned because both are slumming it.
香港湾仔，电器行老板娘（鲍起静 饰）丈夫早亡，她和妹妹共同抚养儿子阿来（张学友 饰）。但后者终日沉迷侦探小说，41岁依然单身，还常会跟想象中的亡父对话。在一场相亲宴上，阿来见到了洁具行售货员爱莲（汤唯 饰），起初有点尴尬，后来在茶餐厅，两人谈笑风生。不过，爱莲一直挂念狱中的古惑仔男友阿旭（安志杰 饰），所以对这门亲事只是敷衍。阿来同样接到了前女友（张可颐 饰）的邀请，出任男模，两人似乎重新擦出了火花。虽然阿来和爱莲各怀心事，但两人却在轩尼诗道再度重逢。与此同时，老板娘却因为报税之事跟老相好（李修贤 饰）闹了别扭，而且，一直蒙在鼓里的她还目睹了阿旭与爱莲牵手逛街。经受不住打击的她彻底崩溃、住进了医院。此后，阿来跟前女友，爱莲跟阿旭的感情却发生了变化……