Here's a post I started in the over 30's "GEEZERS" Group, here at SG. I have included it here for those of you who are to young to join that Group.
Heres a quote of my log from June 02.
Coffee with my ex-boss Cinzia later tonight at Sbucks. She could pass for Monica Bellucci's younger sister - honest! Just ask Lotus ...) 
Cinzia is being considered for a medium sized part in the upcoming Denis Quaid Western! It is currently in pre-production here in Calgary! Strangely enough, they are considering her for the part of the (lovely) daughter of the Indian Chief!
She is swooning over the possibility of repeated takes of romantic scenes with Dennis Quaid! (Lots of beaded suede and leather chaps rolling around together in the dirt, I imagine.)
Now, if only she would break the mold that sees me as an ex-employee; the one that keeps any relationship between us past friendship taboo... 
And yes folks, she is my current crush! 
Cinzia was my boss for 18 months, until 6 months ago. I am the only one she keeps in touch with from work anymore. We go see a movie, or go out for coffee about twice a month. The problem is we always go out as part of a group of mostly women friends, never less than three of us at a time. She still has the "don't date an employee" thing as far as I can tell.
She's Italian, about 5'10, probably around a 36D, 24, 34 (i am guessing on all 3 counts) with long, naturally brunette hair. She is bright, intelligent (which as a Certified Genius, I find VERY sexy!) and good humored like me.
She is, simply put a knockout, as much for her personality as her obvious good looks! I take great pains to not staring at her body, keeping good eye contact between us.
I am so good at not being a learing, drooling idiot around her that she might think I have no interest in here at all. Except, she caught me checking out a rare opportunity of cleavage one time. I just turned around with my eyes down toward the floor, and she was right behind me, not two feet away. She looked right back at me with a knowing half smile. At the time, I imagined she thought, "Finally caught you looking!"
She let it slip at coffee that she's 34; I'm 44 this month. I know that 10 years isn't a turnoff for her. Oh, and she is divorced twice, once when her first husband passed away. I know she's at least into guys, so that's not the issue here.
I get my chance to see her alone when I help her pass her insurance course, she wants to do a weekly study group thing with me four or five times in the next month. She knows I have banking experience, so she wants me to help her with the financial planning side of things.
I am planning something simple, like a bottle of wine to grease the wheels, even though she doesn't drink that often. I want to see if we have any chemistry between us beyond friendship when it's just the two of us for a few hours.
(Anyone still reading this very long winded post?)
So the big question is how do I get this very fine woman to begin to change her mind and look at me differently?
Suggestions, Please!
Any comments from you are welcome!
hmm i don't know - suprise her by taking her out to dinner after studying one night? blarg. i am not good with this thing they call "romance" i still think "show up naked, bring beer" is pretty good.
hmm i don't know - suprise her by taking her out to dinner after studying one night? blarg. i am not good with this thing they call "romance" i still think "show up naked, bring beer" is pretty good.
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Bwahahahahah! That would work for me, but, yeah, I'm a guy...