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What’s appropriate first-date attire?

Posted on August 3, 2014August 3, 2014 by Dating Goddess

After a few good phone conversations, we agreed to meet for afternoon coffee. It was a beautiful perfect-weather day, so I decided to wear a cute summer outfit.  I spent an hour taking a shower, dressing and getting my cute on.

Arriving early, I staked out an outdoor table at the coffee shop. He called to say he just drove by and was parking. That was thoughtful.

So imagine was surprise when he walked up in work-out shorts, t-shirt and sneakers. He obviously didn’t spend a nano-second thinking about first impressions. He knew I was a successful businesswoman. Did he think he would be appealing in this get-up? Or did he think one shouldn’t care how others decide to dress?

While one could argue that it’s shallow to care what others wear, it does set a tone. If one looks like they take pride in their appearance and desires to put their best foot forward, people notice. If one spends a little time deciding how to best show that they put some care into their presentation, it contributes to a positive first impression.

He was smart, articulate, nice and pleasant looking. He asked me questions about myself, but some were the same questions he asked yesterday on the phone. However, it was clear we had different world views, and he admitted he was broke.

So the quandary — since there was nothing odious, do I see him again? Or do I not waste each others time because it’s clear that there’s no long-term potential?

How have you handled such quandaries? See the person again or not?


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Category: Dating after 40

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After her 20-year marriage dissolved, the Dating Goddess dated 91 men in 3.5 years. She shares her lessons, stories and advice for midlife women reentering the dating scene.

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