21 Feb 11

Sasha Speaks: Answering Your Most Private Dating Questions — My Braless Date?

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Dear Sasha,
I’ve been dating this woman that I’m starting to like a lot, the only thing is she has pretty large boobs and goes braless most of the time. I see not only men staring all the time but women as well. Do I say something or not?


My braless date

Dear Braless-
Oh my aching back! I’m having sympathy pains for your poor girlfriends’ breasts. Isn’t she uncomfortable?
I totally understand the burden of being overly “blessed” in the chest area. When I was in junior high, I was totally flat-chested and known as “No-Have-Titty,” after Nefertiti (we read a book called The Egypt Game and everyone thought that nickname was hilarious), or “Sasha, the Carpenter’s Dream: Flat as a Board.” Every night I would cry and pray for bigger breasts.

Then one day I woke up and realized you have to be very careful, and very specific, what you wish for. Without warning, I went from an A-cup to a DD and was horrified. My back killed, I’d get terrible headaches from the weight of my bra straps digging into my neck, I couldn’t jog without wearing two sports bras, my clothes didn’t fit and men would hoot and catcall on the street, and I was just 15. It was awful.

I decided to have a breast reduction when I was 16, but just a few weeks before I was scheduled to have the surgery, a very dear family friend died having the procedure done. Spooked and sad, I couldn’t go through with it and I went back to wearing baggy clothes and slumping my shoulders in an attempt to hide the unconcealable.

Finally, when I was 27, I dislocated a shoulder because of the size of my breasts (to avoid headaches, I would shove my bra straps further out on my shoulders and they popped the bone out of the socket by about two inches) and decided I’d had enough. Even though I was terrified, I had breast reduction surgery and I can now say it was the best smartest decision I’ve ever made.

But it was also the most personal.

You can’t police anyone else’s body. If your girl is comfortable and happy, isn’t that what’s important? You obviously liked what she had going on, with or without a bra, or else you wouldn’t be together. I wonder if perhaps other people’s looks are only now starting to bother you because you’re feeling more proprietary of her and her body, but it’s not up to you how she presents herself to the world.

-Sasha, aka: The Former Carpenter’s Dream

*Feel free to email us with any dating, relationship, love and sex questions you may have for Sasha.

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About Jennifer Kelton

Jennifer KeltonI did not wake up one morning and say “hey I think I’d like a man use my sweater like a towel, write a candid dating book, become a dating expert, the CEO and founder of a social dating site and have three blogs.”

All of this has happened in a slow burn and here I am. The good, the bad, the mistakes, way too many tears shed to count, lots of wine and oh my goodness a huge learning curve that leaves me much of the time saying, “I’m sorry but this is all new to me.”

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