Chutzpah, Childhood, and the Making of a Grandma

For more than half a century, no boys had been born into our family. I am the mother of two daughters — two little dolls who once filled the house with their games of mummies and daddies, schools and shops. They loved clothes, stories, and laughter. They were familiar territory to me; I understood their world completely.

And then, unexpectedly, I fell in love all over again. With whom? With my little grandson.

How I love that word — grandson. And the word that comes with it — Grandma.

Each time he calls out “Grandma!” my heart lifts. It feels like a new name — one I was always meant to have.

When he arrived, I didn’t know quite what to expect.
What would a boy like?
What would he need?
How would I build a relationship with a little boy when all I had ever known were girls?

There are so many preconceived ideas about boys — traps we all fall into, filled with stereotypes and borrowed assumptions. But the truth is, every little boy is different. Every little boy is a reflection of his parents — and, therefore in this case, a part of me. 

I was nervous. But as if by magic, the day he entered my life something shifted effortlessly — as though I had always been ready for this little boy to be here.

Each time I look at him, I’m reminded of my daughter at the same age. Looking at my grandson is like stepping into a time machine, moving back and forth between moments long gone and those just beginning. It is nothing short of magical.

Sometimes, when he smiles, I see the same little smile my daughter used to give me. When he plays shops and restaurants, offering me a bowl of imaginary soup, I’m transported to her childhood playdates with my late aunt — when she would declare that “the chef has left the building!”

He hands me his made-up menu with such sincerity and conviction that I can’t help but think of his mum’s imagination at that age. It is as if he is her mirror.

He has my daughter’s cackle and her husband’s grin. He has her big eyes (like mine), though his are a bright, startling blue — just like his father’s. He has her gift for lighting up a room, and his father’s boundless curiosity. My heart swells with pride when I think of him. His joy is infectious — his laughter, a kind of light.

In yiddish we have a term “chutzpah’ meaning bold and full of self confidence. It is a term that I have always used for my two girls when they would create shows for us on holiday - singing the entire score of Evita from start to finish or reciting whole Woody Allen movies or even affectionately mocking us - testing boundaries and watching us belly laugh till we felt every muscle in our body ache.

I watch my grandson and I see this same chutzpah. He plays off your energy. He mimics. He laughs out loud and pushes the proverbial buttons in the most loving way. He is the perfect blend of my daughters and, in witnessing him, I feel something close to complete — as if life is extending its hand, offering us a second chance to watch our children grow up all over again.

Every visit is a new discovery, a fresh unfolding of wonder and delight. He brings happiness in its purest form, and asks for nothing in return.

How is it possible that a two-foot-tall little boy holds such power? And yet, he does.

Becoming a grandparent is a wonderful thing — but nothing prepares you for the memories it stirs, the nostalgia it carries, even as you look straight into the future. I had no idea what it would feel like to become a grandparent to a little boy after only knowing girls — but I can say, with certainty, that I am deeply privileged to be walking this new path beside him.

A grandmother, here for the new ride, in love with the wonder of it all.

Contributing Article written by: Lisa May

Lisa is mum to Lauren and grandma to Theo (affectionately known as Pretzel). A natural-born creative, she spent over 12 years running a boutique hotel in Marrakech before returning to a life filled with interiors, style, antique fairs, chicken soup, and wholehearted Theo adoration. She has been a tour de force behind all things Pretzel & Jam and played an essential role in bringing the idea from concept to reality.