Letters I Wrote To Myself When I Was Single

Number 6.

Shoes. I love shoes. I always look at a person’s shoes. I try not to judge, but I do. I judge people by their shoes because they make or break an outfit. Literally in my case when I wear heels and promptly fall on my ass and proceed to break some body part. Well, that doesn’t always happen, but the truth is I tend to ruin many a pair of jeans this way. Thank God ripped jeans are making a come back.

But this letter isn’t about shoes. It’s about my 14 hour date and the turbulent wake of perplexing thoughts it left behind.

It started with a Sunday brunch. I don’t usually have dates on a Sunday, but, I had already postponed once, so I figured why not. He arrived 15 minutes late and was such a nervous wreck that I immediately laughed it off.

The beauty and curse of meeting via a dating app is that the initial portion of your first date is completely staged. There is nothing organic about it. You simply talk about the things that you’ve texted about on the app. The random thoughts that aren’t what you really want to say and make you feel as if you are a B-roll extra in a movie who awkwardly laughed at the wrong moment.

Fortunately I am a great conversationalist.

Brunch turned into a game of putt-putt with me purposefully assigning the term “double circle” to my beautiful single-stroke sinking shot. He, ever the avid golfer, simply groaned and shook his head. We were both endearing in our own way.

Putt-putt became a drink on a tree-lined patio. One drink became two as the sun set and the stars came out to play. I started to wonder when the date should end.

We began to walk towards my home. I kept waiting for that first kiss. I didn’t know if I truly wanted it, but I knew it was expected. He felt more like a friend at this point than a date.

And then it happened.

He swung around and pulled me close. I tried not to flinch. The kiss was fine. But the moment was not. How was I supposed to convey that I wanted him to ask first? That I wanted him to slowly pull me close before cupping my face with both hands and saying “I’m going to kiss you now” with an uptick in his voice and an implied question mark at the end of the phrase.

I wanted these things to happen, but they didn’t, and once again I felt empty inside. I tried to smile. He was practically skipping he was so happy. But all I felt was that something was wrong with me.

We walked my dog and once again I wondered when the date was going to end. I knew I should say something, but I didn’t. Instead I asked if he wanted to watch a movie. I don’t know why I said it.

We made our way from my place up the road to his. After walking his dog we put on a movie, one that I had already seen. I snuggled under the blanket but couldn’t relax. I knew exactly what I was doing and it was wrong.

I was testing him. I wanted to see if I could truly trust him. I hated that I had flinched when he spun me around. He hadn’t felt it, but I had, and I wanted to make that gut-reaction go away. So I was being reckless. After all, it was a first date based on the fact that we both had swiped right.

So there I was, snuggled under the blanket with my head resting on his lap feigning sleep. He started with a head rub, which soon turned into a gentle back rub. In many respects he was a gentleman, but not the kind I wanted. I wanted him to scoop me up and take me home. I had already told him that I wouldn’t spend the night and I wanted him to take that literally.

Like the kiss, once again I was hoping that he could guess my thoughts. Like so many women I was afraid to be assertive. Afraid that it would be labelled as “bitchy.” Instead, I wanted him to guess that what I really needed was for him to simply bring me home, like a lost child, to my guardian dog who was waiting for his nightly snuggles. There is no way he could have known these thoughts, but one day, one day someone might.

Someone might actually see all of me. And so, at the end of a 14 hour date, I am left lying in my own bed, waiting for the sun to come up so that my thoughts can finally go to sleep. In the darkness they keep going round in circles and I am left feeling empty inside. Like so many women, disappointed that I didn’t say exactly what I wanted, that I simply wished upon a star and hoped for my fairy tale prince to be a superhero that could read my true thoughts.

And that’s all she wrote, knowing that she would probably give a second date a chance.

XO,
The Improbable Jones

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