Passionate About San Antonio
and the Moms Who Live Here

Shoulda, Woulda, Coulda: Coping with Parenting and Regrets

Looking back over their parenting history, many moms beat themselves up about some facet of raising their children, like the discipline choices they made or how much screen time they allowed their children to have or how much quality time they spent with their kids.

I would not say that I am a big advocate of worrying over the “what ifs” and the “should haves.” Despite this, even though my kids are only 14 and 17, I already have a big “what if” that goes through my head all of the time: What if we had known our boy was really a girl when she was little?

I think about it all the time. Facebook reminds me every day with its “On This Day” feature. When I look at her frown-y, 12-year-old boy face while standing on The Great Wall of China, I wish we had realized what she was going through sooner. Even when I see her as an adorable and happy five-year-old with a crew cut (which she asked for at that age), I wish we had known we were going to have a gender transition in our future.

Our daughter did not come out to us until she was a teen. To be honest, we had no ideanot even an inkling of onethat she was uncomfortable in her skin as a boy. In itself this is not bad, nor is it uncommon. But I often think how much easier things might be now if we had known sooner. One of the big things is wishing we could have started transitioning before male puberty. Many of the changes a boy goes through during puberty could follow her for the rest of her life. Some cannot truly be changed; some can only be changed with surgery; and some only with a lot of training. Her voice, for example, is very deep. If she wants to sounds more stereotypically feminine, she will have to work very hard to do it. These issues make me regret that we did not figure this all out sooner.

“Being a boy” for most of her childhood presents challenges/situations that I never thought I would have to deal with as a parent. In all of her pictures before age 14.5 she looks like a boy, so explaining to people whom I have not seen in a while why I have a boy and a girl and not two boys like they remember is sometimes difficult. But, as a mom, the more important question I ask myself is if the lurking depression and anxiety we deal with now is rooted in a childhood of not being able to express who she was inside.

I may have said in a previous blog post that we are not much about gender norms in our home. We’ve always let the kids play with any kind of toys they wanted. We had Legos and Matchbox cars as well as a pink shopping cart and kitchen. We had baby dolls, Power Rangers, and a whole spectrum of kid-friendly movies to watch.

I scour my memories for things I might have missed. Did I miss that a love of Dora meant that she really wanted to be Dora? Or did the fondness for the cute little animals of My Little Pet Shop mean something? I always attributed the wanting to wear makeup like Mommy at age three to the fact that she was with me all of the time, so of course, she would want to do what I was doing. Were those all cues that I should have noticed? Of course not, because she was all rough-and-tumble boy with a crazy love of Power Rangers and the gross humor of Shrek as well as all of those marginally “girl” things.

I wonder if the years of fussing over clothing options and the two years of having issues wearing the required school uniform of khakis and a polo shirt were because she really wanted the girls’ clothing options.

Does closely examining these historical details of my child’s life change anything? Nope. It doesn’t. But as a parent, I look at how I am performing, jobwise. One could call it a performance self-evaluation. I can’t help myself. Even though I won’t have the opportunity to do better next time.

Can I tell you how different our life would be if I had known sooner? Absolutely not. Not for sure. And in fact, since we have moved so much as a military family, I feel lucky to be in San Antonio where we have all of the resources we need because I know we have lived in places where we would have had no resources.

However, I still wonder if she would have been happier as a seventh grade girl or having at least started high school as her true self? I can’t help but wonder if we were careless in observing her needs and concerns.

Despite all of this, I do know we are doing everything we can to aid her journey. Maybe things will not be perfect and maybe I will wonder for the rest of my life if I missed something, but all we can do (as all parents after the fact) is carry on with our parenting and make the best of the situation and support our kiddo now that we do know.

What would you do differently as a parent? Is there one thing in your child’s life that you agonize over? Is regretting parenting choices even worth the time, energy, and loss of sleep?

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