Two years after the death of her husband, and shortly after her retirement as a high school teacher, Nancy Stokes (Emma Thompson) is ready to experience the one thing that has eluded her for her entire life: pleasure. Booking out a hotel room and a younger sex worker who goes by the alias Leo Grande (Daryl McCormack), she's ready to have the first fulfilling sexual encounter of her life — that is, until she starts having a panic attack, and realizes her desires aren't easy to act upon when they've been repressed for so long. Over the course of several encounters, she starts to open up, but as she talks more about her own life, she finds herself increasingly invested in trying to find the real man behind the Leo Grande persona opposite her — a discovery that will have dramatic consequences.
Much has been written about the scarcity of substantial roles for older actresses, and the inherent ageism in the industry that ensures the parts they do get are never of the sexually liberated variety. The character Nancy Stokes in many ways feels like an unspoken commentary on this stereotypical representation: a woman who has spent her life internalizing all the different ways women are supposed to behave, both in the bedroom and out of it, finding herself afraid to confront any feelings that don't fit into this socially accepted mold.
"Good Luck To You, Leo Grande" is strongest in its early stages, where Nancy's anxieties over participating in the transactional sexual encounter open up a pandora's box of thoughts and feelings she's struggled to vocalize. We learn that everything from her relationship with her children to her abilities as a teacher have been tainted by the same repression that led her to remain eternally silent about her desires. Best of all, Katy Brand's screenplay fleshes this out in a way rooted in Nancy's obvious social anxiety — her relentless oversharing doesn't just play out like a therapy session in all but name, the way a more sloppily written version of this movie would guide the audience towards each emotionally revelatory beat. Everything feels well earned, despite the dramatic contrivances that have led both characters to the hotel room.
It may have more explicit discussions about bedroom behavior than her typical starring role, but the central theme of repression connects "... Leo Grande" to many of Thompson's most celebrated roles. You need to look no further than 1992's "Howards End," for which Thompson won an Oscar for best actress, to find another rich character study about a relationship built between two people who are inherently disconnected, their refusal to confront it provoking lingering unhappiness. Although more explicit in content, "Leo Grande" might be far gentler emotionally — this does, after all, pick up two years after the traumatic end to her previous marriage, the lead character almost ready to follow her heart after decades of compromising it.