Last week, the Commonwealth Shakespeare Company began its 16th annual “Shakespeare on the Common” season with “All’s Well That Ends Well.” We asked Erika Boeckeler—an assistant professor of English who recently returned from a postdoctoral fellowship at the Huntington Library in San Marino, Calif. — for some insight into one of The Bard’s lesser-known works.

What’s the meaning of the play’s title?

The title – “All’s Well That Ends Well” – is repeated several times by the protagonist, Helena. To that end, the play asks, “What does it mean to have a happy ending? The work’s many fairy tale elements play into this query.  In standard fairy tales so many awful things happen, but then everybody seems happy because of the marriage at the end.

There’s often a disturbing undercurrent to the endings of Shakespeare’s Comedies. Think of “Two Gentlemen of Verona,” which ends with a double marriage proposal right after one of the characters almost rapes his best friend’s future wife. Or “Love’s Labor Lost,” where all the marriages are deferred at the end so that the characters can do penance. When they happen on stage, we tend to get swept up with all the lights and costumes and emotions, but when you stop to think about it, the endings are far more disturbing.

What should members of the audience pay particular attention to? What questions should they keep in mind as they watch the action unfold?

Something essential to understand before watching the play is the role of the fool, Lavatch. In general, Shakespearean fools are always very complex and their humor can seem bitter, out of place and sometimes not very funny. This is because they reveal bitter truths or express psychological states of the characters.

Lavatch reverses our expectations and that of the social norm.  As you watch, ask yourself the following questions: Who is he making fun of? In what ways does he show that person to be a fool? How does he poke fun at the social convention of a situation or character? How does his role fit with the darker side of the play—including the many pseudo-happy endings, the frequent deceits and lies and the play’s problematic vision of the future as it comes to a close?

How does Helena’s character stand apart from Shakespeare’s other female protagonists?

“All’s Well That Ends Well” subverts a Germanic fairy tale; instead of a man who comes to an ill king’s court, it’s a woman. What’s more, Helena’s character is a doctor, which was unusual for Shakespeare’s time, and uncommon among his plays. After her jerk of a husband, Bertram, abandons her for Italy to fight in the war, Helena embarks on a pilgrimage to Italy. No other Shakespearean woman takes on something like this dressed as a woman – and if they did, they’d disguise themself as a man.

I think a lot of young professional women can relate to Helena: she’s ambitious, smart, beautiful, rich, at the very pinnacle of her career, and even quite sexual, despite the fact that she has some serious relationship issues.

“All’s Well That Ends Well” is at the Parkman Bandstand on Boston Common, Tuesdays through Saturdays at 8 p.m., and on Sundays at 7 p.m, through August 14. The play runs 2 hours and 45 minutes.