Dressing Up to Date

I’m an unconcerned dresser. I get up in the morning, throw on gym shorts and a sweatshirt hoodie over the boxer shorts and t-shirt in which I slept, and think I’m presentable. It’s scary, but quick and requires no thinking. Truthfully, I’m in this snappy outfit until around noon. If I do have to go anywhere, I usually put on jeans and a short or long sleeved t-shirt depending on the weather –not a fashion statement but again, mindless. My Mother on the flipside spends half the morning going from closet to closet to closet deciding what to wear. This includes her shoe and purse selection. I did not inherit these genes. When I visit her, she stares at what I’m wearing and asks me if I want a piece of her clothing as a gift. It usually comes with a cape. “No Mom I hate capes,” I whine every time and head for the fridge. 

My laissez faire attitude towards dressing makes going on a date difficult, coupled with the problem that unlike Mom, I only have one closet and it is half full. My friend Adria can attest to this as she stood in front of it one day screaming that “No self respecting Jewish Princess would have so little clothing.”  My deepest apologies to all the JAPS who I’ve failed. Yet even I don’t go on a date in my gym shorts and hoodie so I have my work cut out for me when it comes time to get ready. It’s hard to keep my head from exploding.

Saturday night, it took six outfit changes to get out the door. White v-neck shirt with black skirt and little gray jacket was my initial instinct. Nope, wrong jacket and the skirt looked weird with the t-shirt. I flung it off. The black skirt with black top and black blazer that I tried on next would only work if we were eating at a funeral parlor. Off it went. Little black cocktail-ish dress? Nah, too dressy . I whipped it onto the bed. Skinny jeans with white shirt and black blazer. Very Soho but not exactly right. I threw the shirt across the room – it landed on the dog who looked dizzy from the watching the flying clothes. I was close to tears but not close to being dressed. I rummaged through the remaining things in my closet but it all became one black blur and I was running late. I desperately pulled out a tight black v-neck shirt, put the skinny jeans back on and black blazer. Hmmm, not bad, understated yet chic and since I was worried I’d damaged my rotator cuff with all the changes, I gave a thumbs up to “Beefy Boy” and he followed me with t-shirt still draped on his head.

I groaned as I stared back at the clothes strewn all over my room and couldn’t help but wonder if dating was worth the clean up.


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7 thoughts on “Dressing Up to Date”

  1. please, once you have kids and are married, you have to dress up for the stupid suburban mom parties…mom jeans are just not acceptable…dating seemed easier! 🙂 fun article

    1. Wow Mom parties. I’d be lost. Be a trail blazer and wear jeans. Dating is not, I repeat, not easier….less driving and quieter but not easier.

  2. Instead of too much thinking about your clothes when dating and maybe not enough the rest of the time, you need to find a happy medium. That’s my method. And try to avoid situations that require/expect suits. But then I don’t date either (except with the wife).

    1. Well I’m sure your wife inspects you before you go out to dinner etc?! Or does she totally trust your ability to pick an outfit. Men have fewer choices…although then again I don’t have many choices either which is part of the problem. Then there’s my Mother who has four closets packed with clothes – many still with the tags on! I have not followed in her footsteps and Lord knows she tried to show me the way.

  3. From my experience dating has become a lose/lose – never used to be that way. Whoopsie, I forgot to stop dating!

  4. For the record, I have jeans, tee shirts, shell tops and a variety of shoes. In the summer, my pants switch to shorts or skorts. I am a casual person, but sometimes I have meetings where I have to feign professionalism so I have to business suits tucked away as well. That is my wardrobe so I can commiserate even if I don’t have the dating thing going on! Very good story.

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