One enchanted evening, 37 years ago, I met Ann at an industry dinner party. Sitting next to one another at a large round table in a noisy restaurant, conversation soon revealed we’d both grown up in Brooklyn, attended – at different times – the same high school and college, and later lived one block from each another on the same street in Manhattan. 

Now in Los Angeles, 3000 miles distant from past coincidences, fate brought us together in real time, this time as neophytes in the same industry, with nearly identical interests in film, literature, music and design.

The Positive Nature of Diversity in Friendships and Business

During the next three decades, we’d work together more than once for the same company, partner-up to start a new company, then Ann would work for me successfully in two separate business ventures.

Diversity Made Our Friendship Strong

Diversity, not similarities, made us indispensable to one another in all the iterations of our multi-faceted relationship.

In early days, when I was more likely to rush to judgement, Ann’s influence helped to slow my response and encourage more carefully considered options. Conversely, my early warning antennae on business issues allowed for proactive solutions that kept us ahead of a fast-moving business curve.

Money and Politics

Ann’s view on the use of money bent more conservatively toward the long-term. My tendency to float a dozen ideas at a time, begged for immediate funding. Compromise between the two philosophies and belief in each other’s strengths, provided the strongest resolutions.

Regarding politics, where saner minds don’t often prevail, our views are the most divergent, yet we both wish for a peaceful world and common freedoms for all.

Respect, Trust and Mentoring

If respect is sacrosanct, the potential for volatility in friendship and business can give way to unshakable trust. For us, it led to an unexpected bonus: best-case examples of reverse mentoring and problem-solving.

Here are some examples of how this mashup of age and experience played out against the backdrop of our friendship:

• I was a firebrand in my early career. The even-keel of Ann’s wisdom softened my rough edges.
• Less self-assured of her own business acumen, I bolstered Ann’s confidence, propelling her growth and visibility within our profession.
• Ann’s life experience provided a sounding board for my personal relationship issues, while my professional experience drove her toward stronger professional associations with key influencers.
• When finance issues moved us toward the edge of reason in business, the ability to play off each other’s strengths kept us non-toxic and able to locate true north in tough situations.

What You Look Like Through the Eyes of a Friend Can Be Illuminating

Relationships needs constant rekindling.

Today’s social media can restrict interaction between friends to the least number of key strokes. We’ve become satisfied with the non-sustainable act of toe-dipping into the lives of our loved ones.

Ann and I have maintained a counterpoint to the banality of Facebook or Twitter: a four-decade history of (very) long lunch engagements. These meetings are seminal, treasured events taking on an intense, in the moment flavor reminiscent of the 1981 film, My Dinner With Andre.

We come to the plate – quite literally – with news of our lives. We share sincere interest in each other’s familial circumstances and a healthy dose of curiosity about each other’s internal lives. It all adds up to a solid pulse check on each other’s emotional geography.

Good Friendship, Like Good Jazz, Must Be Both Cultivated and Spontaneous

Our quarterly lunches are like comfortable musical improv sessions that benefit from friendship shorthand.

In quick succession, we rifle through a host of pent-up topics – from serious to frivolous – then riff off each other’s ideas until ready to settle on a few themes. Hairbrained schemes may be hatched, but one of us inalienably pulls the other to the ground if hot air lifts our thought-balloons too close to the sun.

We frequently laugh and never forget to hug it out before taking leave of each other’s company.

Our Friendship Code – If We Had One!

• Use intuition but take nothing for granted.
• Make delicate course corrections, when necessary.
• Respect the differences among equals.
• Swim deeply in the pool of friendship gratitude.

Do you feel male/female friendships can enhance your life? What are the benefits of a male/female friendship? How valuable is diversity in your existing friendships? Please share your thoughts in the comments below.