“Happiness is Not Always Fun” - especially when you are finding love and acceptance within a May-September romance. The road is filled with extreme highs and terrifying lows. How does a corporate executive on a beautiful Jamaican getaway find love with a local who’s 20 years her junior? How does a widow navigate a relationship with her immigrant partner without being shunned by her racist family, neighbors, and friends in post-war Germany? Both films are suffused with the implications of societal rule running corrosively within our interpersonal relationships with others. Although the prospects of dating younger men are tempting and momentarily gratifying, can they ultimately achieve happiness, or have their newfound freedoms been diverted to other, softer levels of entrapment?