Adult Playdate: What to Where

It's your first date, put down the lipstick

By DivineCaroline
Published: Apr 03, 2008

Damn, my hair looked too good. I tried to unperfect the perfect straightening job by slapping on a little extra smoothing balm to make it look greasy, and then pulling on and off a tight woolly hat to achieve a convincing head of I-didn’t-try-too-hard-hair. This was my first playdate and I didn’t want to alienate my potential new friend by looking too pulled together.

Jessica and I had exchanged phone numbers and noncommittal we-should-get-togethers months previously, but it was an accidental encounter earlier in the week that had lead to actual plans for breakfast. Our kids knew each other so we’d chatted a few times at sports or school events, but never without the distraction or crutch of the kids. She needed help translating the lyrics of an Irish song, so we made plans to meet after dropping the kids at school.

A kid-free playdate.

I could wear white if I wanted to…but white in winter might be too eager. Black? No, it might be too slimming. Pink? Too girly. Floral? Trying too hard. Grey? Yes, grey. You really can’t go wrong with grey—it’s stylish but it’s also just grey, and grey is just fine. I settled on a light grey cashmere hoodie—the hoodie kept it casual, and the cashmere would keep me warm. Perfect.

Now, what to wear with the hoodie? Definitely not a dress. The one thing I had learned in my years of dropping kids to school is that out of respect for (read “fear of”) the other moms, you just don’t wear a dress until at least 11am, with the exception of jersey dresses (a jean alternative) in summer, and only then if worn with flip flops and a chipped pedicure. It’s part of the unspoken mom-code. Lip balm not lipstick, antiperspirant stick not perfume, and sneakers or flats, not heels. Hats are appreciated because they imply unbrushed hair, and an effort to hide it (rather than comb it). It’s okay to look like you’re off to the gym, just not okay to actually mention it (unless you follow up with self-deprecating references to your fat ass and lumpy thighs).

I detest the drop-off drama and so I have avoided befriending “the moms,” though I’m sometimes a little jealous when I see them hugging and chattering at the school wall. It’s impossibly difficult to find time to “make friends” as a grown woman, so when Jessica—a sane, normal, and interesting person I’d actually enjoyed chatting with—suggested plans, I was eager to appear similarly sane, normal, and interesting (surely I could pull together a look to fit this part?). I imagined she wouldn’t notice, never mind judge, my outfit, but I was making an effort (not to make too much of an effort) just in case…

After eliminating the dresses and all the pants in my closet (for varying mom-code violations), I wavered between my one pair of fitted but almost threadbare jeans that I wear all the time, and my one pair of wide-leg jeans that I should wear all the time, but I somehow always end up swapping for the threadbare pair right before I leave the house. I relaxed as I felt my playdate outfit come together: a grey cashmere hoodie, with a white (but not brand-new white) tank top, and a pair of wide leg jeans.