Letters to Anita: On My Grandmother’s Legacy -The Toast

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The author's grandparents, Anita and Bill

Shortly before my maternal grandfather died of prostate cancer, he gave my Uncle Bill, his eldest son and namesake, a box full of things whose inheritance he wanted to ensure while he still could. Its contents included, among other things, an official MLB baseball of uncertain context, a program from JFK’s 1961 inauguration, and most tantalizingly, a manila envelope that read, in Pop-Pop’s Sharpie scrawl, “Letters to Anita: Do Not Open Until After I’m Dead.” He had underlined “Dead” three times, in case the seriousness of these instructions was lost on us.

The Anita referred to was, we knew, my mother’s mother: Anita Sheridan, née Origlio, who died on Thanksgiving Day in 1988. Born four years too late, I never got to meet her–a shame whose enormity has been impressed upon me for as long as I can remember.

The spectrum of Catholic devotion among Sheridans is broad, but my mother and her siblings are in religious agreement on at least one point: the intensity of their reverence for Anita. Remembering her is as much a Christmas tradition as homemade Bailey’s or my Aunt Michelle’s horseradish-encrusted london broil or the gentle ribbing I dutifully endure every time I reach for that third helping of mashed potatoes. Not for nothing was Anita nominated for Willingboro, New Jersey’s Woman of the Year. Decades after her death, she can still work a room like no other.

These glowing accounts of my grandmother’s life are equal parts fascinating and envy-inspiring, like the apotheosis of the “Wish You Were Here” postcard. They all miss her terribly. Every year I want to join in that giddy, tipsy chorus of recollections about the vanished matriarch, but the gulf is just too wide. How do you make memories with a phantom? Anita’s posthumous presence is less ghost than patron saint. She’s a woman canonized by the self-reflexive miracle of her own enduring legacy.

For all of these reasons, it was difficult for everyone to heed my Pop-Pop’s scrawled request not to look at the letters until after his death, but we did. He passed away in late August, a few days shy of my 17th birthday, and the family reconvened that October to finally open that much-wondered about package, precious as a Dead Sea Scroll.

Inside was a trove of letters my grandfather had written Anita, his then-fiancé, over the course of 1954 and 1955 while he pursued an engineering degree on the GI Bill and she worked multiple jobs, saving up for their new life. While the premise seems almost Nicholas Sparksian, the letters are blessedly un-saccharine. Instead they are filled with the kind of mundanities I might communicate to my boyfriend in dashed-off text messages. There are quick summaries of what he’s been up to at school, nights with friends recounted, reports on the number of hours he’s slept (admirably many), and jokes about the rising price of antifreeze: “Six dollars for two gallons! It costs almost as much as whiskey.” Not much, probably, to please Allie-and-Noah style romance diehards.

Still, my grandfather wasn’t cold. He admitted that he wasn’t much of a smooth correspondent—”This hasn’t been much of a love letter so far but then again I’m not too good at that sort of thing,” he wrote on November 2nd, 1954— but this only makes his self-conscious attempts at tenderness more poignant. In lines like “Even though this may be a short message you may be sure it carries the deepest sentiment and affection. Please don’t laugh at this as I really mean it,” you can practically feel him blushing, working up the confidence to commit those lines to paper in his lopsided hand. There were certainly times where he fumbled the compliment completely, despite his earnest intentions: “I was trying to think of another way to tell you how much I loved you but one idea per letter seems to be my limit. The fact still remains, however, that you are the light of my life, even though you do get a bit dim (not meant to be derogatory) when that fiery temper gets a bit out of hand.”

But the theme that Pop-Pop most frequently returned to when trying to flex his romantic muscles was the notion of unspeakability. It wasn’t just shyness or a literary handicap that made waxing poetic so difficult, but the size of the thing he sought to describe— its power. It was the kind of love that could only be gotten at obliquely, like watching an eclipse in a mirror.

I can’t think of many things to write about just now so I’ll just tell you how much I love you, how do you like that. It really is something that can’t be put into words but I’ll give it a try anyhow. The thing that impresses me most is that I have such a nice feeling when you are around me. I hope that someday I can make you very, very happy. If I could only find some way to make this time at school go by more quickly, then I would feel a lot better. I just keep hoping I’ll find some way to earn money that will bring the big day a lot closer.

As much as I love these letters, they are not quite the cipher for Anita I once hoped they would be. The desire to access my grandmother–the woman, not the myth–has become twice as acute in my frustration. Who wouldn’t want to know the person able to inspire so much tenderness in an often stoic man? Greedily, I have latched onto the few glimmers of trivia the letters do offer: that she loved fashion, that writing the letters had been her idea (or insistence), that at least once she did his English homework for him, that she could choose a wickedly funny Valentine. But with her half of the correspondence missing, the letters to Anita are like a trace–they can only suggest their opposite.

The author's grandparents, Anita and Bill The author’s grandparents, Anita and Bill

Still, this absence is a kind of clue itself, one that says more about my Pop-Pop than it does about her. Anita horded his letters for years, preserved in their carefully opened envelopes; my grandfather did not do the same with hers. That he secretly held onto the letters she’d saved for another twenty-one years after she died, even through a second marriage, is certainly a testament to their relationship. That possible Anita-revelations were thwarted by his youthful lack of foresight would perhaps disappoint me more if there didn’t exist a kind of corollary to this document.

My grandfather was a late-blooming archivist, but toward the tail end of Anita’s life he produced a masterwork. In a cabinet in my mother’s bedroom, there’s an ordinary marbled composition book that reads: Anita C. Sheridan, Wishes & Thoughts, Nov. 13, 1988 & Subsequent by William A. Sheridan. The book is bloated from inserts and age-curled pages. Begun just eleven days before Anita died, it is an unflinching index of grief. He dutifully recorded Anita’s last-minute funeral requests; logged the flowers, mass cards, and written condolences sent in her name (363 total); and wrote of looking forward to the day when he could hold her again in God’s eternal kingdom.

The journal is an open wound, and he sought to staunch the flow by stuffing it with sentimental totems: dried flowers from Anita’s funeral (“they were pink roses from me”), cards exchanged in the last year of her life, a drawing my cousin Jocelyn gave her on the day that she died, a long-leftover thank you note from their wedding. Near the end there is a letter from my mother’s cousin in Colorado. She writes, “I never really got to know Anita well, but she has seemed like such a big presence in my life.”

Yes. I know the feeling.


My mom, if I have not already made it abundantly clear, is Irish-Italian Catholic, while my father was a secular Jew who found God in AA and converted to Lutheranism after my parents married. Technically I was baptized a Catholic, though I grew up with Christmas and Hanukkah, Easter and sometimes Passover. We attended Trinity Lutheran Church as a family until my parents split up and–much to my relief–the welfare of my eternal soul was downgraded in importance.

This complicated heritage has left me not so much with a crisis of faith as with an absence of it–a profound ambivalence for the whole enterprise of religion as well as its self-satisfied deniers. Once, in middle school, I did briefly toy with the idea of youth groups after I joined the school play and found myself orbiting a small clique of Baptists. I disposed of this notion just as quickly, though, after hissing “Oh my god” when a piece of the set collapsed unexpectedly, scandalizing my would-be friends. More recently, I dodged emails from a campus rabbi who reached out after I verged on hysteria trying to answer his simple question: “Are you Jewish?”

On the whole, I’ve found it easier to name the things I’m not: Catholic, Jewish, Lutheran; atheist, nihilist, solipsist. When asked about my religion, I will sometimes say “nothing,” but the connotation feels wrong. I don’t want to call it a lack. It might not be here, but it doesn’t feel missing.

My mother’s most frequent lament is that I am, quote, so earthbound. She isn’t wrong. I admit that in some ways this has interfered with my ability to feel a cultural or spiritual kinship to Anita. Her legacy is so embedded in the language of the church that I sometimes feel like a heretic just speaking her name. My grandmother was an officer of the Altar and Rosary Society of the Corpus Christi Roman Catholic Church; my mom frequently refers to her as its “pillar.” I know all the words to the Catholic grace we say at every Christmas dinner, but I feel like an imposter with every recitation. And unlike my mom, I can’t make myself believe that Anita continues to observe us from on high. Like time, my lack of religious conviction has kept me at arm’s length from her.

I used to think that the only thing that really connected us was a trajectory of loss: Anita’s mother Adeline died when she was sixteen, my mom was motherless at twenty-seven, and I lost my own dad shortly after turning nineteen. Teenaged Anita mourned her mother with poetry: ”And as you look on me below / I hope that in your soul you know / I miss you more than words can say / And I hope to be with you someday.” My college thesis became a series of essays about my dad’s life and the void that was left when it ended. These twin impulses we shared have comforted me, even in their morbidity.

Recently, though, I’ve been able to access another kind of closeness to Anita–because, not in spite, of my terrestrial inclinations. The little West Philly studio apartment I’ve occupied since August is just four blocks from the house where Anita was born and lived for more than a decade. And while the demographics of the neighborhood have likely changed considerably since the 1940s, the architecture is much the same. Many of these streets are lined with houses more than a hundred years old, proudly adorned with metal plates that announce the year of their construction. One block east of my apartment building is the Hanson Haines House, a hulking and turreted residence built in 1902 for the Quaker banker whose name it bears. Whenever I pass it now, I wonder: did plaid-skirted knee-socked Anita ever pause here and try to get a peek inside? Was she curious about whoever lived in such Victorian splendor? Did she know them? It’s unlikely that I’ll ever follow in Anita’s footsteps in any proverbial sense–that churchgoing, homemaking, mother of four–so I’ll be satisfied inhabiting them instead. A small piece of geography will suffice.

My mother insists that Anita would have adored me, that we would have been fast friends. I do know that she would have loved me, maybe even more than in that obligatory familial way; I’ve been assured that there was nothing perfunctory about her. But I worry, sometimes, that she wouldn’t approve of me. I am too godless, too opinionated, too frequently red-lipped. I’ve worn a translucent blouse to Christmas dinner. I can’t write a damn thank-you note. I will never let a man change my name.

Dear Anita, I’d like to write, I hope that you would have forgiven me.

Yet the more generous part of me knows that this anxiety is probably unfounded. Anita did, after all, once stay out late at a Jersey shore dive bar just to watch my mom win $500 playing Bruce Springsteen’s “Jungleland” in a talent contest. She had, I’m sure, her fair share of fun.


In late December my mom drove me back to Philadelphia after a few nights spent sleeping in my adolescent bedroom for the holidays. As we approached an intersection near my apartment, she asked about an ornate building in her peripheral vision: “Do you know what that is?”

“It’s a Catholic church,” I told her. “St. Francis de Sales.”

“St. Francis de Sales?” she half-shouted (her emotions, like mine, are characteristically outsized). “That’s where my mother went to elementary school!”

St. Francis de Sales is the last church I stepped foot in, months before this revelation from my mother, on a sweaty night in July. I was walking down 47th with my boyfriend and another friend, my stomach an alchemical mix of carnitas tacos and in medias res ice-cream cone, when we noticed the big doors to St. Francis were propped open. With no plans to speak of besides getting mildly drunk to Paolo Sorrentino’s La grande belleza, we decided that a detour might be worthwhile. St. Francis had long been an object of passive interest for all of us–an inevitability, really, considering its massive gilded dome, so unlike anything else in our West Philly neighborhood.

Inside, it smelled like incense–not the thick patchouli that often wafts from the white dreadlocked shoppers at my local co-op, but a holier variation. Subsequent Google searches have confirmed my suspicion that it is beautiful in the way old churches almost always are, which is to say that in my own memory it has been hopelessly confused with any number of other churches I have warily, touristically entered. Boosting St. Francis’s aura of divine authenticity was the presence of a genuine Irish priest with the lilting brogue to prove it, who, after ascertaining we were passersby–not congregants–began dutifully to inform us of the various Masses (English, Filipino) and services offered there. Perhaps he’d managed to sniff out the presence of lapsed Catholicism, but probably he was just doing his job.

I have always resented being proselytized, but an accent and advanced age can go a long way towards softening my attitude, if not my agnosticism. So it follows that when the priest asked if he could–or rather, told us he would–bless us, before we went, it was not hard to acquiesce. The three of us stood there silently, heads bowed, as he spoke: me with one arm extended through the still-open doorway, so my ice cream wouldn’t drip on God’s tiles. I didn’t know, then, that the trip had been a pilgrimage. But I think that Anita would have appreciated my manners.

Jess Bergman is the studio manager for a popular children’s book series and has probably seen every picture of a puppy posted on the internet since 2012. She lives in Philly.

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