Sasha Speaks: Answering Your Most Private Dating Questions — Bigger Boobs?

Dear Sasha,
I have a huge issue I have a very flat chest can we say A cup my boyfriend keeps wanting me to get a breast enlargement and said he will pay. I have never had a body and or breast  issue up until now. Should I do it and what are the risks?


Bigger boobs?

Dear Boobs’ Boob,
Supposedly there are boob men and ass men, but your boyfriend sounds like both a boob man and an asshole. What a jerk! The only person who should ever decide if they want to alter their body is YOU and it’s never anyone else’s place to say, “Hey baby, you know what would make me love you way more? If you had a hotter rack. On me, of course.”

I can tell you from experience that plastic surgery is filled with risks, pain and, sometimes, death.

I have the opposite problem as you; I’ve always had very large breasts. From the time I was 15, I had back problems and neck problems, not to mention pounds of embarrassment from men ogling and catcalling me in the street. I desperately wanted to have a breast reduction but after a dear family friend died having the procedure done when her anesthesiologist forgot to monitor if she was breathing (she hadn’t been for ten minutes and spent three weeks in a coma before passing away), I was too fearful.

I waited over a decade following her death, miserable with the two elephants strapped to my chest, but finally had the surgery a few years ago. Even though it was painful, terrifying and extremely expensive, I can honestly say it was the best decision I ever made. But I made it for myself.
You don’t need a breast enlargement, you need a boyfriend reduction. Ditch that loser and find a man who will love you the way you are.


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

  •  Good advice. You are not a thing, his possession so he can “upgrade” the way he wants. I am not against these procedures, but only if person decides for themselves and not under pressure of the others.

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About Jennifer

Jennifer Kelton

Jennifer Kelton CEO / founder LLC is a Los Angeles native and a pioneer in the worldwide dating industry, investigating the game of love while providing encouragement and support since 2007, starting with the acclaimed dating book Don’t Use My Sweater like a Towel. An accomplished CEO, visionary and entrepreneur, Kelton’s work in the […]

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