Ann Workman is a small town girl. Now on a cruise with her ill husband, she spends her time dreaming of the big “what if”: What if she had been brave and made it to Stanford for graduate school as her college professor Albert advised instead of choosing a small New England college without the same intellectual vigor for her studies? In the Swinging Sixties, surrounded by celebrants of the psychedelic joys of the era, would Ann have had a very different life, and would her first love, Jimmy, still be the beat of her romantic heart?

DEAR ANN is a series of letters in the midst of Ann’s fantastical ideas about where her life could have gone. This format gives Bobbie Ann Mason a chance to concoct a sweet love story but also wrestle with the possibilities of the road not taken, as well as the chance to find a gold ticket in what is real.

"Mason has created a novel that addresses the zeitgeist in a very subtle way, and it is a welcome antidote to the intense reading choices available in women’s fiction."

In her ’60s fantasy, Ann is a young woman who revels in her innocence. The loud and seemingly endless lovemaking of her next-door neighbors drives her nuts. She is a romantic, looking for the perfect boy to grow old with against the prevailing attitudes of the times. Ann believes in sleeping with people you love, although she eventually partakes of the free love her friends espouse. It’s a good way to relax after the strident intellectualism of her Stanford professor. When she finally finds the right partner, her life takes on a rainbow of joy and pleasure that goes well beyond her expectations.

Mason is well known for her homespun tales filled with warmth and gentle wisdom about the realities of this earthly existence and its subsequent slings and arrows. However, in DEAR ANN, the Ann of the fantastical future seems like Dorothy in Oz --- mouth agape, incapable of accepting the liberal factions and the new mores that she is being confronted with in California. How much of her imagined existence would have really changed her in the way that Mason presents it?

Ann seems unlikely to throw herself willingly into these circumstances after so little exposure to such new ways of living. The ’60s, the music, the drugs, the clothing, the ideas are all so enticing, and even the inclusion of the hard facts about the Vietnam War gives the era a sheen of glowing perfection that seems wrong for Ann’s Kentucky upbringing (her mother’s letters to her about life back on the farm are interspersed with the other letters she uses to create a timeline). It feels as if there is a depth missing here in place of gentle reflection and surface-area fantasy.

However, Mason does a good job of accessing the actual past and editing it to make the most impact on her characters. When Ann writes in a letter that she “goes to sleep on a surrealistic pillow,” she references both the trippiness of the general lifestyle and the music of the era (Jefferson Airplane, for those of you too young for ’60s music). The experiences of Jimmy, the fears of Albert and the steadfast home musings of Ann’s mom all create a warm bubble of interaction for Ann that helps incorporate the fun elements of the time with the more difficult ones.

DEAR ANN feels like a perfect book for quarantine as we think about what has been, what will now not be, and what we now most hope for in all of our lives. It is a natural aspect of aging that one would think back and wonder about the road not taken. Mason has created a novel that addresses the zeitgeist in a very subtle way, and it is a welcome antidote to the intense reading choices available in women’s fiction. Focusing on “what if” is a far more winsome experience than trying to figure out who killed who and how people in the past survived fascism and totalitarianism, or some millennial love story with dysfunctional love.

For older readers, DEAR ANN will fill a void that many new novels by younger writers cannot fill --- with wonder and hope of a different sort and plenty of wisdom to go around.