If you distill a play to its most central conflict, how often would the residual sentiment be this question: What makes a life worth living? In Holiday at Arena Stage, this oh-so-human dilemma gets an old-timey, glam, and festive makeover under the direction of Anita Maynard-Losh. The play, which is one of dramatist Philip Barry’s most famous works (alongside The Philadelphia Story) centers around a young, on-the-rise Wall Street lawyer who hopes to make it big before cashing out to enjoy life in all its simple pleasures, an approach to happiness and success colored by his working-class upbringing. His fiancee, who belongs to an elite, wealthy family, isn’t too pleased. Her unconventional, open-minded sister, on the other hand, is more than a little intrigued. Set in the 1920s, this classic romantic comedy, with all its musings on class, wealth, success, and the infallibility of love, is just as funny, charming, and thought-provoking nearly 100 years later. The play eventually became a 1938 film starring Cary Grant and Katharine Hepburn—one of many adaptations over the years—and promises to address the question of how to live a full life with wit and sparkle. Holiday runs from Oct. 7 through Nov. 6 at Arena Stage. arenastage.org. $56–$72.

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