The latest production from Portland Stage takes you back to a time when things were a little bit simpler. Well, maybe not all that simple, as the main and only onstage character lets you know.

Theresa Rebeck’s 2003 play “Bad Dates” is a warm and engaging romantic comedy from a time, not so long ago, when cities were vibrant arenas for fast-paced living and some complicated cultural changes had yet to fully emerge. Still, the ultimately uplifting message of personal discovery within the play balances nicely with its essentially light touch to make for an entertaining 90 minutes of theater in 2021.

A great deal of the credit goes to veteran professional actor Annie Henk. She brings to life Haley, a 40-ish single mom who is looking to reenter the dating scene after finding a somewhat tenuous career path working at an upscale restaurant in 1990s New York City.

Haley frets about how to approach her renewed social life, directly telling the audience of her initial trepidations and later disappointments with several dating partners who she has met by chance, by misguided fix-up or through an attempt to rekindle an old flame.

She moves restlessly about her wide bedroom in an apartment she shares with her 13-year-old daughter Vera, an unheard, offstage presence from whom she occasionally seeks fashion advice.  She also consults by phone with her brother, alternately asserting confidence and falling back into insecurity as the list of her dating debacles lengthens.

If only she can put together the right outfit from her overstuffed closet, Haley thinks she will be good to go. She tries several different looks during the performance (costume design by Rodrigo Muñoz), from prim to sexy, always giving particular attention to her large collection of shoes. She seems to believe that if she can find the right pair, not only will they fit comfortably and be indisputably cute but wearing them will lead to the rest of her life falling into place.

The dating situations described may seem a bit familiar to those accustomed to experiencing this sort of light comedy from any number of movies and TV shows. But reading the author closely, Henk and director Jade King Carroll (who was the last to direct an unlimited seating production at Portland Stage before the pandemic forced changes last year) have captured the pathos around all the witty observations about the trials of mid-life dating.

The set design by Anita Stewart suggests the clean but cluttered lair of someone hoping for new horizons to open in her life. Some references in the script to an old Joan Crawford movie are intriguing and a subplot about gangsters provides a shortcut for Haley to reach the next level in her social life. But it’s her heart-to-heart sharing with the audience, as movingly communicated by Henk, that wins the day.

Haley charms less as the loveable flake she seems to be in the early going than as the more three-dimensional character that emerges from the rubble of her bad dates. By the close, she has earned a measure of affection for her spirit.

Steve Feeney is a freelance writer who lives in Portland.

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