Dear Sasha, I’ve started doing the online dating thing a couple of months ago, and I’ve been talking to one guy in particular for a few weeks before we decided to meet in person.  He looked really handsome on his profile pictures, but I figured most everyone put up their best pics online, so without being hideous, he probably wouldn’t be as handsome when we meet.

We finally met last week, and OH MY GOODNESS! He’s ridiculously GORGEOUS!!! He’s very well-mannered, tall and athletic, with piercing blue-green eyes, and a perfect smile! I’ve had crushes before, but definitely not that intense.

So there’s my issue. I’m not that great looking. Well I’m definitely not unattractive, but I’m aware of myself, and I’d be say a 6.5-7 on a regular day, an 8 on a really good day. That guy’s a 12! He’s so out of my league! Seriously, he’s bringing out all of my insecurities! R


I just want you to know that everyone reading your letter right now doesn’t feel the slightest bit sorry for you. As long as you know that we can continue….

So, I was just recently having a rant with some of my bros about how many minging-ass looking dudes I see with hot chicks. A day doesn’t go by without me seeing a beautiful woman on the arm of someone who might as well be a hobo. Now this is going to be a gross generalization but I’m sticking to it: women tend go for personality; men tend to go for a set of perky tits and ass. I'm not saying that's why they stay, but it's generally what they're first attracted to.

I can think of only three, THREE!, women in Hollywood who've hooked up with dudes that are "out of their league": 1. Fergie 2. LeAnn Rimes and now after seeing that rat tail at the Oscars 3. Deborra Lee-Furness, but I don't even know if beards count in this category. Anyway....that’s it. The end. Now just think about how many famous old, gross, jacked-faced men are with insanely beautiful women. TONNES! I mean, Mickey Rourke, who looks like he’s had 1000 skin grafts, is with a 25 year old model.

So here’s the deal R – you’ve just found a diamond in steaming pile of sh-t. So instead of feeling insecure, it’s time to f-cking rejoice. Maybe, just maybe, this guy is looking for substance over the superficial. YAY!

That said, this just all speaks to the f-cked up bullsh-t society feeds us every day and as women it's time we ask ourselves why men are allowed to feel like they deserve it all and women are not. So R, instead of asking if you deserve this guy, maybe it’s time to flip the script and realize that you not only deserve the best of ass out there, but you’re going to own it.  

Hope this helps and keep me posted!