Know the rules well, so you can break them effectively. -- Dalai Lama XIV

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Step by Step

Published on March 27th, 2014 | by Deesha Philyaw


DEESHA PHILYAW Is Breaking the Rules: Why I Love My Kids’ Stepmom

Know the rules well, so you can break them effectively. — Dalai Lama XIV

Confession: I’m an accomplice to some serious rule-breaking. Recently, my kids’ stepmom, Sherry, called to ask if I could watch her 2 ½-year-old daughter, Mika, my daughters’ half-sister. I’ve babysat for her on numerous occasions, but unfortunately, “Own-ee” wasn’t available this time. (“Own-ee” is what happens when a wee person tries to say “Aunt Dee”). And I was a bit bummed about it; there’s nothing like fake screaming when Mika pops out of a cabinet in my dining room after I say, “Where’s Mika? Oh, where did she go? Where could she be?” Over and over and over again. My conversation with Sherry wandered from my regrets and happened to land on my oldest daughter Taylor’s after-school plans that day. Sherry thought she was picking Taylor up immediately after school, but the last update I’d gotten from Taylor involved her going with friends to an overpriced coffee place near the school and then getting a ride home from someone’s mom. Apparently, it hadn’t occurred to Taylor’s “teenage brain” to tell Sherry about her change of plans. Can you spot the violations of stepmomdom in the above scenario?

Rule 1: For the sake of healthy boundaries and your own sanity, don’t try to be friends.

Sherry and I have vacationed together, swapped cars when I needed to haul around more children than I had seatbelts for, shared meals, and attended family counseling together. At the bus stop on the first day of school one year, a neighbor kept staring at Sherry and me, and pelting us with prying questions, trying to figure out our relationship to my children. (Mike, my ex-husband, was traveling that day). I think she thought we were a lesbian couple. When we finally gave the nosy woman a break and explained that I’m the kids’ mom and Sherry is their stepmom…the look on her face said that as homophobic as she may have been, it would have been easier for her to take in a romance than our true relationship.

Rule 2: Co-parents should communicate about the kids and the schedule only with each other, not with 3rd parties such as stepparents.

We do adhere to this rule in a big-picture sort of way. Mike and I create and maintain the parenting time schedule. We make the kids’ doctors’ appointments and all decisions related to their schooling, extra-curriculars, discipline, and privileges. We have frequent, informal, two-person conversations about their overall care and well-being. But there are times when it’s just been more convenient and practical for Sherry and me to talk directly to each other about the schedule, or, for example, for her to take one of the kids to the pediatrician. Mike, Sherry, and I seemed to recognize around the same time the impracticality of his always serving as an intermediary, so we talked about it and agreed to relax the rule.

We know the rules that we are breaking. Mike and I have recommended them to thousands of co-parents and stepparents since 2008 when we co-founded And we’ve seen what a positive and necessary difference these rules have made in the lives of stepparents, co-parents, and children. I have been known to quote Wednesday Martin’s Stepmonster chapter and verse.

But it’s been six years since Sherry came into our lives. Rules that provided boundaries in the beginning have relaxed, opening doors over time. My daughters would have had a much harder time being open to getting to know her if I hadn’t been explicit about the fact that I too welcomed her into our lives. This is not to say that her relationships with the girls don’t have some of the usual stepfamily challenges, but to my knowledge, a loyalty bind isn’t one of them.

Deesha, Sherry, and the girls

Deesha, Sherry, and the girls

Recently, a scheduling mix-up caused me to miss my daughter Peyton’s birthday celebration at school. I’d purchased the treats she wanted and expected to deliver them to school, but I could not be there at lunch time to help pass them out. Sherry happened to be at my house the night before when I was delivering this bad news. Peyton’s tears dried instantly when she learned that Sherry could come to school at the designated time. Even though Sherry and Peyton have a rocky relationship, there are still moments such as these when she embraces Sherry, figuratively and literally. We celebrate every small victory between Sherry and Peyton because not only is there a stepmom-stepchild dynamic, but both of them are adopted.  As Sherry once described one incident of Peyton’s rudeness toward her, “Peyton’s 6-year-old adoption issues were having a knock-down-drag-out with my 34-year-old adoption issues. And we were both sobbing and screaming.”

While there are some important differences in their adoption stories, Mike and I have a greater understanding of Peyton because of Sherry. Of course we’re in family counseling, read books and learn from other adult adoptees. But, I am so grateful for Sherry’s transparency with me about her own adoption-related concerns and for the insights she’s given me into my child’s experience. This exchange is woven into the fabric of my relationship with her.

But I know this same insightfulness can also be a source of pain for Sherry. The “evil stepmom” stereotype and the “second wife” stigma are hard for any woman to contend with, but for an adoptee, they can compound fears of abandonment and feelings of inadequacy. This is one reason why when Sherry has felt the need to step back in her role as a stepparent for her own emotional well-being, I have understood and supported her.

I often joke, “I’m just thrilled to have another person to drive these kids around!” Seriously though, Sherry is much more than another mom-chaffeur. She loves and cares for my kids, even when it’s not easy to do so. I love and appreciate her heart and her willingness to show up emotionally, each day, for what I know is one of the toughest jobs on the planet.

Sadly, my husband is in a very high-conflict co-parenting situation with his ex-wife. So, Taylor and Peyton are aware of how having a relationship with me comes at a high, painful emotional cost for their stepsisters. They understand, secondhand, what it’s like at the other end of the spectrum of stepfamily experience. But they also know another double stepfamily in which both beloved stepmoms (one couple is a same-sex couple) volunteer and attend events at school, participate in carpool, and are involved in birthday parties. Ultimately, they understand that many more stepfamilies fall somewhere in the middle of the spectrum.

Often, Cold War prevails over civility. How did Sherry and I get lucky?

For starters, Sherry and I first met in a rather unorthodox way. She had been dating Mike for three years and had not met the kids. I knew she existed because, like spies, Mike and I would quietly call or text each other our locations if we thought we might run into the kids while out with our new partners. We lived in the same neighborhood and frequented a lot of the same places, and we weren’t yet ready to make those introductions.

Then one day, I got a call from Sherry introducing herself. I think it was just supposed to be a short call to make plans to meet, but we ended up talking for two hours. We met for breakfast later that week at my favorite brunch spot. We sat outside, and it was like hanging out with an old friend. Sherry has a sharp sense of humor and a contagious laugh, and we laughed a lot that day. I don’t remember what all we talked about–except, oddly enough, our respective pain-in-the-ass mothers–but I remember feeling very comfortable with her, and with the idea of her meeting the girls. So after we got to know each other, then she met my kids.

Looking back, what strikes me about that first phone call and meeting is that neither Sherry nor I seemed to view the other as a potential adversary. Her domain is her relationship with Mike, and I have no interest in inserting myself there. My domain is my relationship with my children, and Sherry has no interest in inserting herself there. Yes, the domains overlap, but we are both secure in what is ours. Sherry would later tell me that she just wanted a chance to forge some kind of positive connection with my girls, not usurp mine. And I wanted the girls to have a positive connection with their new stepmom. I wanted to help, not hinder, their transition into stepfamily life.

And the other thing that became apparent by the end of my breakfast meeting with Sherry? I like her. I remember saying those words to shocked friends.

Finally, I believe my friendship with Sherry stems in part from my own upbringing. Even though my parents never married, and my father was an inconsistent presence in my life, my mother made a conscious commitment to my relationship with one of my half-sisters. When I was three and my sister Trice was born (I tend to drop the “half-”), my mother and Trice’s mother, Debra, both young and unmarried, initially squared off as enemies. But sanity prevailed, and according to my mother, they decided that while our father was unreliable, it was important for Trice and me to be close. My mother explained, bluntly, “We knew that one day, Debra, your dad, and I would be dead and gone, and you two would still have each other.” Pretty gloomy stuff for such young women, but my mother’s words turned out to be prescient. My childhood was spent with Trice regularly at my house, or me at hers. Over the years, our relationship with each other grew to be stronger than either of us had with our father.

When my father and my mother both died in 2005, Trice was my main support, emotionally and practically. The day my mother went into hospice, Debra and Trice were there. When they walked into the room, my mother smiled and said to Debra, “See. We knew our girls would need each other.”

With my mother and Debra as models not for what has to be, but what can be, I think my default would have been to be welcoming of any kind stepmother and half-siblings my children had. Sherry has simply made it easy. I consider her friendship to be a gift, to me as well as to my children. It’s been worth it to break the rules.


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About the Author

Deesha Philyaw hit the mom trifecta: She is a biological, adoptive, and stepmom to 4 girls ages 10, 15, 15, and 17. In collaboration with her ex-husband, she is the co-founder of, and co-author of Co-Parenting 101: Helping Your Kids Thrive In Two Households After Divorce. She is also the co-facilitator of “Writing Through Your Divorce,” an online workshop for women.

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