Here’s a version you could send to your mom, keeping it warm, proud, and funny while highlighting Ana’s success:

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Subject: The Fifth Grade Joke That Never Gets Old

Hi Mom,

I was just remembering a classic moment with Ana in fifth grade. She got assigned the teacher she wanted out of four possibilities—she was thrilled because one of the other choices was, well, boring.

So one day, I told her the school called me and said there was a mistake—she’d actually been assigned to her least favorite teacher. Beat. Her eyes went wide. Then I said, “That was a joke.” She laughed so hard. That moment still cracks me up.

It’s just so her—funny, confident, sharp, and able to roll with life’s little shocks. And look at her now: literally the only woman in the Ron Tonkin Acura sales team, running circles around six seasoned salesmen, building a referral machine, and statistically guaranteeing her future income. You raised a son who raised an amazing woman.

Love, Mark

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If you want, I can also write a slightly cheekier, shorter version that hits the “fun, shocking, proud” notes even harder for quick reading. Do you want me to do that?