The Kind of Woman I Absolutely Love to Have as a Friend

They are role models who know how to mother.

Jennifer Cannon

Published November 13, 2025

illustration of woman with older friend packing plants in car trunk, older friendship

Lily Qian

I am now in my late 50s, and based on how my life began, it makes perfect sense why I’ve been drawn to developing friendships with older women.

Doesn’t everyone live with a grandmother? That’s what 7-year-old me remembers thinking. I spent my first eight years with Gram after my mother was unable to care for me due to mental health issues. My parents had split while I was still a baby.

I lived in an idyllic bubble with Gram in a historic garden apartment in Sherman Oaks, California. Its residents, including my grandmother, were middle-aged or retired. By the time I was in kindergarten in the early 1970s, I would wander alone and know of at least one Gram-approved neighbor whose doorbell I might ring for a game of Chinese checkers or a glass of lemonade.

I spent little time with children my own age outside of school, despite the fact that I had cousins from my paternal side who were close in age and lived less than a mile away. I didn’t know at the time that my grandmother’s own anxiety prevented her from socializing too much.

My father married for the third time when I was 8 years old to a woman with three children. I was sent to live with them several months before the wedding, before my father moved in.

On one of the first nights with my new family, without my dad present, my stepmother sat me down to explain that my mother had abandoned me and didn’t love me. She said that she was my mother now — and that I should call her Mom.

A mental switch flipped, and I remember thinking, This lady is wrong and I know my mom loves me. I also knew instinctively that going along with my stepmother was the best course of action. In this new living situation, far from the calm and quiet of the only life I’d known with Gram, the people-pleaser in me was born.

Now, it's easy to see why my stepmother went to great lengths to ensure my mother and I wouldn’t have a relationship. In those days, my mother’s crippling anxiety was hidden behind stunning beauty and a confident air. This veneer was intimidating to my insecure stepmother, in spite of the fact that we rarely saw or communicated with my birth mom.

Throughout my adolescence, I was fascinated by my friends’ mothers. In young adulthood, I always had a few old-enough-to-be-my-mother friends. Latching onto (no pun intended) strong women who were not my mother helped me navigate some of the toughest periods of my life.

As a teenager, there was a Best Friend’s Mom. This mother didn’t bat an eye when I ate more cookies than would be considered polite during a sleepover. I marveled at the carefree laughter and banter between my friend, her sisters and their mom. Their house was happy and relaxed. It felt “normal.”

When I left home at 17, desperate to escape an extremely controlling and emotionally damaging environment with my stepmother, there was my Boyfriend’s Mom. She was a wonderful woman who would, briefly, be my mother-in-law. Before we were married, she took me in without hesitation or judgment. She made me feel safe and loved. We had deep talks about life, and she even shared some personal secrets.

At the age of 19, this ill-equipped mom, now of a 1-year-old, I’d recently had what I remember as being a joyful reconnection with my biological mother. However, she warned: “You know, Jennifer, we’re not going to have this mother-daughter thing like you think we are.” I didn’t hear her. I thought I could fix her and didn’t fully understand her mental health issues.

At birth, maternal connection isn’t guaranteed. There's a kind of ambivalence that’s born from wanting a relationship and the realization that it can never be, because it never was. I’d been trying to force something with my mother that wasn’t viable.

Around 30, fate led me to Realtor Mom. She sold me my first home, and we became fast friends. She took me under her wing and became a powerful mentor. I’d been heartbroken after a recent breakup. Moving boxes sat for weeks until one day she showed up and helped me unpack.

She did it with me, not for me, and had a knack for injecting humor without minimizing my sadness. When she noticed I was going out a lot to bars in search of love in all the wrong places, she talked to me about it without making me feel ashamed. She was concerned for my well-being and knew how to give me a proverbial swift kick in the most productive way. After a devastating job loss, she created a position for me at her office.

Meanwhile, I’d developed a deeper relationship with my paternal aunt, who, next to my grandmother, is the closest thing I have to a mother. At 33, marrying for the second time, I really wanted my parents there. It was a big deal for my mother to travel across the country to attend, and I didn’t want anything to jeopardize that. Though I was not surprised when my father said he wouldn’t come.

There was a big upset and, when he spoke to my aunt about it, she stood up for me. And, most recently, she inspired me to reconcile with my father after more than 10 years of estrangement.

In my search for validation and a sense of normalcy, I found tangible pieces of mothering in older women who saw something in me that needed nurturing. Their layers of experiences were fascinating, and I was eager to absorb whatever pieces of wisdom they would share.

With three children that span two generations, my oldest is about to be 40, and my youngest just turned 20, I am now the older mom who is nurturing some of my daughters’ friends. I’ve always hoped I could be that comfort and guide as so many of my older friends have been to me.

Do you have many friends who are older than you? Let us know in the comments below.