When Is a Risk Worth Betting On?

This entry is part 9 of 10 in the series My Adventures So Far

I wonder if I’ll recognize love if it happens, or if I’ll not trust it and run for my life.

I enjoy men and love sex, but just like in Las Vegas, I’m compelled to cap my losses. Before I sit down at a table, I’ve set a limit on how much I’m willing to risk…when I’ll pick up my chips and walk away. It appears I’m following the same strategy when dating, yet they are two vastly different games. In blackjack I evaluate the cards on the table and only have to decide whether to hit or stand. The dealer doesn’t care what I’m wearing or how my hair and makeup look. They’ve got their eyes on my hands and my bet.

So many more facets to dating than when I was seventeen…the last time I was single. LOL  I feel like a high school freshman. I had no idea dressing for a party or a date could be so daunting. Half way through my shopping trip for a dressy party, I was ready to drive to a convent and sign up. I’m not even Catholic. The overzealous sales woman, determined to ‘play on my attributes’ she said, brought me form-fitting dresses with short skirts, or open shoulders, or necklines so deep I could see my navel. “Men like to see your skin, a little cleavage, your legs.”

“What about my bright eyes, spirit and straight teeth?” I wanted to ask, but figured she’d tell me those were things horse traders looked for. Unfortunately, all this undressing took place in a fitting room, under florescent lights, and I made the mistake of leaving my glasses on.

Evidently, she didn’t see the puckers in a two-size-too-small-form-fitting dress I was afraid was going to rip and she’d want me to pay for it. Comfort is not even a topic on the table here. Thank goodness, I finally found a great dress in my size, so she got some commission for all her optimism. It has three-quarter sleeves, not so short I’d leave a personal touch on a restaurant chair, but getting in and out of his car would require the tight legged sit and swivel in. The dress also sported a scoop neckline that touches both my collar bones, and flash. Gold sequins and a glimmer on the fabric in between. If I don’t eat or drink between now and the party, it will be even better.

As I hung it in my closet, it stood out like a neon lamp planted in a dark dog run. I realized I’ve been dressing down (jeans, sweatshirts, sneakers…makeup, but wholesome girl look.) Then it hit me. What if I dress to impress, reveal a little sass, perhaps attract attention from a man? Then I don’t wonder what he wants…am confident in that arena, but know it’s superficial, about sensation, not emotions. Then I immediately wonder if I’m jaded.

Is the truth that frumping up is like hedging a bet, taking out insurance because I don’t expect to win…only get a seat at the table, a chance to play the game?

Since then I’ve shopped a bit, tried to lose the quite-so-wholesome look, risked an off the shoulder sweater and sparkles on my shoes. Step two is not to feel self-conscious doing it. I’m a work in progress.

Still…I wonder if I’ve been dressing down and dating to prove to myself I’m happier alone, keep picking up my chips and moving on because I’ve reached my risk limit, or if I’m ready and willing to play in earnest. Take a seat at the table, look the dealer in the eye and say, ‘I’ll double down, without insurance.”

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