“Can I get 10 minutes of free consulting time? Not work-related…” The text popped up on my phone on a recent Saturday afternoon while I was painting my bathroom. It was from a previous client I had done some communications work for a year or so ago and I could not imagine what she needed with the caveat of it not being “work-related.”  I replied sure and asked when a good time was to talk.  She responded, “Now.”  I quickly popped in my earbuds, loaded my paint roller for another swath across the wall, and hit the call button.  

“I know this sounds crazy and I can’t even believe I’ve gotten myself into this but I’m having an anxiety attack and need your help,” the voice on the other end of the line said.  “What’s going on?” I asked, “and how can I help?”  “I have a DATE tomorrow and I don’t know what to wear!” 

How many of us 40+ women are navigating the dating scene the second time around? UGH!!! Is there anything worse?  What to wear is just the tip of the iceberg.  

This sweet friend went on to tell me that in 15 years of being divorced, she had maybe 5 dates and none of them made it to second dates. This tells me where her headspace is.  Let’s face it – as a single, working professional mom, who has time for the full-time job of dating?  We barely have time to take care of what is already on our plates. How are we supposed to introduce another human being who is a stranger, with his own baggage and needs?  Yikes!  I get it. I’ve said a million times, if I didn’t have the partner I have now, I wouldn’t be dating at all.  Starting at square one over and over again holds no appeal.  I just don’t have the bandwidth or the intestinal fortitude.  

So, I admire my friend – and anyone – willing to put themselves out there and give it a shot.  Hard things are good to do sometimes.  And you never know until you try.   

I started asking questions: how did you meet him (online)? Where is he from (New York but now lives in Houston)? Where are you going (brunch at a hip downtown hotel)? All these things informed my advice to her.  This was a first date with a guy from an edgier urban background, at a slick, hipster locale.  A floral sundress wasn’t going to cut it.  And the Sunday mid-morning time frame called for a more casual approach. A look that doesn’t look like you’re trying. I quickly rattled off: skinny jeans, a vintage t-shirt and a blazer with the sleeves zhouzhed, a pair of gold hoop earrings, some bangle bracelets, and depending on how you’re feeling either a flat embellished sandal or a strappy kitten heel sandal, and a small crossbody bag.  

I could hear her relief over the phone.  This wasn’t rocket science, nor did I come up with the solution to peace in the Middle East.  But when you’re spun up and nervous, even the simplest decisions are monumental conundrums.  But I could see my friend sashaying into this cool new whimsical hotel in downtown Austin, looking effortless but stylish, with a nod to the rock-n-roll vibe of Austin (vintage t-shirt), but also to her very professional career (blazer repurposed).  And jeans are the official uniform of Austin – a city that refuses to get dressed up for anything.  This choice gave her the home-field advantage by saying “you’re on my turf.  This is my city, and this is how we dress.  I’m not making any special effort for you,” while still looking cute and fashionable.  

As much as AFL promotes stepping outside your comfort zone in getting dressed, trying new things, and being bold, there is a time and a place for the familiar.  When you’re feeling overwhelmed and are overthinking a situation, go back to your basics.  Wear what makes you feel good and feel most like your best self, whether it’s the first time around, or the second, or even the third or fourth.

Images by Breezy Ritter