The thing about having a teeny teenager is that when it comes time for her to get dressed up mostly formally for friends’ Bar- and Bat Mitzvahs, we sort of get stuck between a rock and a hard place. Or, say, a babyish dress that fits or a grown-up dress that my child doesn’t have half of the bod for (and her mother really doesn’t want her wearing anyway).

If we shop in the kids’ section, things tend to be a little too frilly and sometimes full of rhinestones and Hello Kitty. If we shop in the lady section, Emily swims in an xs. Or the dresses are $300 which NO. Or she finds the perfect dress, emails it to me and by the time I get around to taking her to the store, the dress is sold out in her size. (Mom of the Year right here)

So we look and look and look and look and look.

After a particularly disappointing session of her trying on 11,000 dresses and finding exactly not one, we stopped at Starbucks in the hopes of making my headache go away.

“Mama, I think these two are on a first date.”

And just like that, our day got infinitely better, even dressless. It was like watching a movie—a really awkward, funny, uncomfortable, hilarious, cute, sad movie. The poor guy, while adorable (no, really adorable) was just trying too hard.

I think the exactly moment that lost him the second date was when she said she would probably feel uncomfortable working in downtown Toronto because it was too busy and she’d be too invisible…and he told her that everyone would notice her as she walked down the street. (Oh honey no.)

“So, are you on Facebook?” he asks, smiling.

“No, I hate Facebook.”

“Oh, I’m not either,” he lies.

“Right? It seems so voyeuristic.”

“Oh, I agree!” he lies.

“And everyone’s always checking it. Like, they can’t stay off of their smartphones!”

“Oh, I agree! I hate my phone!” he lies, as he shoves his smartphone into his pocket.

(Oh honey no.)

This became such a great teachable moment for Miss Emily—How to behave on a first date (Don’t be nervous! Don’t try too hard! Be yourself!) —and such an interesting question for me, who, well, hasn’t been on a first date since 1996—How would I behave on a first date.

I wonder if my quirks would make me interesting (or possibly make me undatable.) I like to listen to the same song for many hours in a row. I like offbeat movies. I like burritos. I love social media. I spend a lot of time at garage sales. I am always overdressed and/or like I belong on season 2 of Mad Men. I am hopelessly terrible at laundry. I don’t sleep. I am physically unable to dance. I tend to be kind of, um, adorkable. (I like the word adorkable). I can speak fluently in movie quotes. I have old lady tendencies. I wear socks to bed. I am afraid of clowns—and kind of the shower.

Well, I guess if I follow the advice I give my daughter (WHO OH MY GOD IS GOING TO BE GOING ON DATES SOON HOLD ME) to not be nervous, to not try too hard, to be herself, I would be totally awesome on a first date. And a second. (Yay for me?)

This gave us just enough energy to go to one more store and ended up buying the most adorable, glove-fitting, age-appropriate dress. Thanks, first daters at Starbucks.