I don't like dating, but I like being in a relationship, so dating is a necessary evil to get there. I have found that the feelings dating stirs now, in my 50s, is not that much different than in my early 20s. Excitement. Anticipation. Anxiety. Nervousness. Doubt. Could this be the one? Is he a serial killer? Does he have all his teeth? Does he talk like Donald Duck?
After my last breakup in February, I took a couple months to heal. By the end of April, I was ready to dive back into the dating pool. The waters in that pool are murky and filled with ominous creatures. Every once in a while, you find someone treading cautiously and you make a connection. But you have to survive all the snakes and frogs first.
Last week I had what I referred to at the time as a first date. I will no longer call them that. This was a first meet. Nice man, but not the man I'm looking for.
The first meet is always a bit of a carnival ride. Feelings run the full gamut and this is what makes picking an outfit so challenging.
Anticipation and excitement have me wanting to dress nice for the occasion. I want to make an effort, show that I'm interested. And, you know, add a bit of the wow factor. I've had several dates where the guy did not make an effort and while I tried not to be judgy about that, it did make an impression. At least ditch the t-shirt. When I'm teaching my Presentations with Pizazz workshop to the Speech and Research students at the high school, I always tell them to dress one level up from their audience. Seems like good advice for dating too...dress one level up from your usual.
But, at the same time, I don't want to set unrealistic expectations that this is how I always look. So there's the dilemma.
People offer advice about being yourself, and I always am. There's a side of me that likes to dress pretty, and there's a side of me that likes to hang out in pajamas. I'm not going to show up to a date/meet in pajamas.
I wear dresses and skirts as casual wear. When I have a long drive or travel by plane, I wear a maxi skirt. It's just more comfortable than pants and works in any weather.
So a dress or skirt is a viable option for this occasion because it does show a side of me. But so do the jeans and a tank top.
Last summer, I went on a first date where I rode my motorcycle to the meeting place. I had my patched vest with all the naughty sayings, my hair in a braid and a headband on, jeans, Harley boots, no make-up. It's not that I wasn't making an effort to look nice, but when I ride, I can't be bothered with anything girly. It just isn't practical. So he got to see me in my natural summer habitat. He wasn't deterred and it is probably the best first date I've had this century. It led to a second date where I wore a pretty dress and heals and jewelry and make-up. Too see the look on his face was priceless and worth all the effort. Second date led to a third date where I was back on the Harley.
For my meet last week, I finally settled on simple jeans and a nice tank top. Nothing fancy, nothing sloppy. I was going to put on a little make-up, but I was also buying a new car that day and the excitement and frenzy of that adventure had me rushing out the door without any make-up. I realized this an hour from home and was like, oh well, he's going to meet me in my most simplest form.
It was a nice meet. He was very nice and respectful. Alas, there was no spark and I won't settle for anything less than a chemical reaction. So, I'm still treading in the murky waters and I'll likely go through the clothing dilemma again. When that happens, I'll remind myself the outfit doesn't matter. In my experience, men don't care what you're wearing. I like the idea of dressing casual for the first date and dressing up for the second, making him earn that little bit of extra effort.
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