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Tim Ward and his son Josh – who climbed Mt. Kilimanjaro together

Maybe it was the thin air, maybe it was the mountain symbolism, maybe it was all that time together – but Tim Ward and his then 20-year-old son, Josh Holober-Ward, embarked on the father-son conversation of a lifetime while climbing Mount Kilimanjaro in 2010.

During the ascent, Mr. Ward revealed the reasons why his marriage to Josh's mother failed, and admitted to having affairs. Intimate, detailed and surprising, the conversation was a game-changer for the pair.

"For me it was a deeply moving experience, like transformational," Mr. Ward, now 53, said during a recent interview in Vancouver, where he used to live. "The coming clean just clears the ground for there to be a friendship based on equality."

There are things about their pasts that parents may never want their children to know. But there may also come a time, as Mr. Ward discovered, when full disclosure can open the door to a deeper connection. Deciding when and how to shed light on the dark corners of your past is a judgment call that experts say should be made on a case-by-case basis. While it worked out for Mr. Ward, having the big talk while camped on the side of a mountain may not be for everyone.

"It doesn't need to all happen in one conversation," says Ruth Slater, a psychologist with the Hospital for Sick Children in Toronto. "Whether the child is young or grown, it's important to make sure that the child's best interests are being considered, and that takes precedence over a parent's interest," she adds. "There's a need to put yourself in the child's shoes and try to figure out how this might impact them."

Mr. Ward planned the trip hoping to repair a serious rift that had occurred more than two years earlier. That's when Mr. Holober-Ward, whose parents had shared custody since they split when he was a baby, chose to live with his mother full time and cut ties with his father. While they resumed a relationship six months later, Mr. Ward wanted to strengthen the fragile bond.

Four days into climbing Kilimanjaro, in a tent at Karanga Camp 3,995 metres above sea level, Mr. Ward revealed the reasons behind the divorce, confessing, among other things, that he had strayed outside the marriage repeatedly. (The discussion is detailed in his new book, Zombies on Kilimanjaro: A Father-Son Journey Above the Clouds.)

Mr. Ward says he wanted his son to know the real story of his life. "We parents kind of build our own mythology that we want our children to believe in. It's kind of like we're God and we give them the gospel of who we are and also who they are," says Mr. Ward, who was born in Ottawa and now lives in Bethesda, Md.

"Our stories are just like the clothes we wear that serve a purpose, but they're not who we are. And when you stand naked without your stories, that's really freeing. … Josh and I at that moment were free to start whatever relationship we wanted."

Still, was it a case of too much information? Absolutely not, says Mr. Holober-Ward.

"It was like a best friend sharing his deepest secrets about who he was and really letting me see him for the person that he is, rather than the perfect father."

It's one thing to accept relationship flaws in a parent, but as Vancouver-based novelist Billie Livingston found out, a life on the edge is a tougher sell. Her father, now 86, was largely absent when she was growing up. She says he was a hustler who made his living playing cards.

A few years ago, she says, her estranged father called and asked her to lunch. As they drove to the restaurant, he began to tell her stories about his life. "I wanted to know the details, but … I wanted him to go beyond the details. I wanted him to suddenly have some kind of epiphany about himself as my father. Like somehow we were breaking ground," says Ms. Livingston, now 46. "We would somehow be more honest and learn who each other were, and he'd be dad." That discussion ended in tears and essentially ended the relationship. Her father's life – and this incident – inform Ms. Livingston's recent novel, One Good Hustle, in bookstores this week.

Even if the personal information a parent shares is in no way shameful, parent-child talks can be a minefield. Being open and honest throughout child-raising is how Vancouver city councillor Tim Stevenson and three other co-parent/step-parents have navigated a non-traditional situation with relative ease, hoping to never have to sit the kids down for that One Big Talk.

When Mr. Stevenson started a relationship with Gary Paterson, a minister, they began a series of conversations with Rev. Paterson's daughters, who were 5, 3 and 1 when he split from his wife. Shortly after, Rev. Paterson's estranged wife fell in love with another woman. The young girls – now in their 30s – were raised by two same-sex couples who shared equal custody and a belief in continued, candid conversations.

"We started young, but always, of course, age-appropriate," says Mr. Stevenson.

Their approach seems to have contributed to family harmony. On Aug. 2, the two couples will throw a party to celebrate their 30th anniversaries. The three daughters and now four grandchildren will be there.

Saleema Noon, a Vancouver-based sexual health educator, says parents should operate at their own comfort level when revealing details about their lives – and sexual history in particular. "But be careful," she adds, "because being too secretive or evasive might send the wrong message about sex and sexuality to your kids."

She says that when explaining the reasons behind a divorce, even to grown-up children, parents should be honest, but use discretion: "Adult children have a right to have an understanding of what happened, a general understanding as to why their parents' marriage broke down."

Mr. Holober-Ward, who before Kilimanjaro had a vague idea that his parents' breakup had something to do with infidelity, says that knowing what he does now about his father makes their relationship more satisfying. While his friends are stuck in a world of parent-looking-out-for-child, he and his dad have developed something better.

"We both understand that we had a strictly father-son relationship and that we filled those roles, but that's in the past," said Mr. Holober-Ward, shortly before embarking on a kayaking trip with his dad in northern B.C. "We're done with the whole raising and fathering thing. Now we can just be man-to-man friends."

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