Recently, one of my daughters and I were in the car together driving to the dermatologist’s office for an appointment to check out some pre-pubescent acne. It is a rare occurrence that her sisters aren’t tagging along, so I relished the opportunity to chat with her about the upcoming school year, and other things we don’t have nearly enough time to discuss, like her love of Pitbull and new skins on Minecraft, whatever that means.

As we rode along, she meekly asked, “Mom, why do I have to go to the dermatologist?”

“Oh, it’s no big deal,” I responded off-handedly. “You’ve inherited Dad’s genes, and we just want a doctor to look at your skin to see what we can do to clear it up. And we want to make sure we do whatever we can to make you feel good about yourself.”

“But I already feel good about myself,” she replied quickly.

The words stabbed me right in the heart. Did I just tell my daughter that the way she looked right at that moment wasn’t good enough? Did I inadvertently slam her body image? Why didn’t we discuss this more and let the choice be hers?

I decided to slam the brakes on the conversation and take a different route.

“No, honey,” I stammered. “That’s not what I meant. You are perfect just the way you are. We just want a doctor to look at your skin to make sure you don’t have an allergy or infection or something like that. It has nothing to do with how you look.”

Phew. That was close to being a body image fail.

“So these pimples mean I’m sick?” she nervously asked.

Crap, I’m right back in it. Now I’m scaring her. Way to go, Mom.

“No no, no. It doesn’t mean that at all! I just meant when you have a reaction to something going on in your body, it’s good to have a doctor check it out,” I said too quickly, hearing my voice get higher as I tried to dig myself out of the hole.

“Like when dad had the wart on his foot?”

“Um, yeah, just like that.”

And then radio silence until we pulled into the parking space. In real-time, I think it was two minutes, but in awkward-parenting moments it felt like three days.

I put my arm around her shoulder as we walked through the office building door, and all I could think was I thought I would be better at this.

I thought I would be better at talking to my kids about the difficult stuff — the stuff that made me die of embarrassment when my mom tried to discuss it with me. I read books about discussing sex and articles about promoting health body image and blog posts about getting through puberty. I listened to my girlfriends as they talked about issues with their daughters and took mental notes. I even bought the American Girl series on puberty — all three books!

I wanted to be my daughters’ source for information. Although my mom swears she had “the talk” with me, I think I blocked it out like a traumatic experience. Are You There God, It’s Me Margaret was my go-to source for getting through puberty.

Most importantly, however,  I wanted to make sure my girls felt comfortable enough to come to me with questions before they put themselves in a risky situation — or after if they ever found themselves in trouble.

I wanted to be a boss at awkward conversations with my daughters.

Well, not so much.

When we talked about bras, one daughter was most interested in knowing if she could get one of the thick, squishy bras, like mommy has. Apparently I’m raising a future Victoria’as Secret model.

When I tried to explain sexting after a friend caught her daughter just a year older than mine sending inappropriate photos, the conversation yielded a series of giggles about how disgusting boy’s “private parts” are. Despite my best efforts at a serious conversation, all I got was: “Who would want to see that?”

And my personal favorite is when I tackled the topic of menstruation with my girls, and one of them ended up bawling because apparently I made her believe that you get pregnant every single month. “I don’t want to have a baby every month,” she wailed. Epic fail.

I sucked at this. None of these difficult conversations went according to plan despite my best efforts.

I thought I would be better at this.

Or so I thought.

The other day I took my daughters to Claire’s to spend some gift card money. While there, a young girl sat screaming in the ear-piercing chair, begging her mother to let her out. For ten agonizing minutes, the child screamed while the mom negotiated with her to go through with the piercing, but she continued to cry and stuck her head between her knees.

Listening to them broke my heart. I unknowingly shook my head as I helped my daughter pick out some earrings. That’s when she turned to me and said, “Mom, no one should make you do anything to your ears that you don’t want them to.”

Yes! Yes! We had a conversation about respecting bodies sometime in the past. We talked about that.

And then this summer, my daughter hastily jumped out of the pool. I asked if she was okay and she told me a little boy, a four year-old friend of ours, was touching her inappropriately. “He keeps grabbing my butt, Mom. I know he is little, but he’s not listening, so I thought I would just get out of the pool.”

We talked about that too! Taking yourself out of difficult situations and not allowing others to touch us in ways that make us uncomfortable. We talked about that.

And then my youngest burst into tears one night for no apparent reason. I suggested that maybe she was tired, and she replied: “Maybe. Or maybe it’s those moaning things you talked to us about.”

“Hormones?” I said to my 9 year-old. “I don’t think that’s what it is. But I’m glad you are listening.”

Even the conversation on the way to the dermatologist, the one that broke my heart, demonstrated my daughter is doing okay, even when I flub it up. She confidently told me she feels good about herself no matter what —and I can’t ask for more than that.

Puberty, sex, drugs, alcohol, driving, bullying, boyfriends, body image, guns. etc. The list of things we need to discuss with our kids is long and never seems to end. I’m going to keep tackling these issues, as awkward and painful as it may be for all involved.

And although I thought I would be better at this.

It will be better because I tried.

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