A real rare challenge

Reply Sat 29 Oct, 2016 07:52 pm
Here it is, I know you know the story . I know her since primary school; she was distinguished among other girls. Few years later, junior high school, was among the first who grew breast, still distinguish, and then reach high school and be a real hottie, sexier than lot of playmates when they were cool. Difficult to reach though, simply because back then was cool to date older men. She had poor grades as expected, but always someone will to help her till school finished and got married to, yes you guessed right, someone in mid twenties (she was about 20 when married)
Now, 24 years later, still the same hottie, ehm, 24 years older though (definition of MILF ) ,two children in early adolescent (boy and girl) and divorced, which I discovered quiet recently when for some reason checked her facebook profile but not sure exactly when, but definitely recently
About me. Single, never married, casual relationships almost always and same age. Sometimes we bump and we have friendly salutes or some compliments (never loose chance to tell her that she’s the same as she was, which is true, and she answers the same for me, which is also true) but not something more,neither mutual close friends . Through years she has developed some sort of social life that most of married women do (charity, sport and culture champers, latin dance lessons and all that) , and as I saw in her profile she goes out more often, with other women in her age (yes, I do some e-estalking )
Answers “go ask her out NOW ” is out of discussion. In such case it’s more than likely that I would be rejected and ridiculed ,not to mention that I don’t know proper timing, whether she’s ready or not. Of course I would like to date her (remind you that we talk about a very very hot girl), and if universe conspire and go beyond dating would be awesome, not only because she is hot, but I see it as a challenge to pursue dream of my adolescent too without to care that much. Many will ask, then why did you write all that? Simple. To check how satisfactory forum answers are

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Reply Sat 29 Oct, 2016 07:57 pm

40new20 wrote:

Many will ask, then why did you write all that? Simple. To check how satisfactory forum answers are

Golly, I sure hope someone steps up to the challenge.
Reply Sat 29 Oct, 2016 08:06 pm
Why not you? Just imagine you are me, and think "it would be cool if I give it a try in the most discreted way possible" . What would you do to approach her first?
Reply Sun 30 Oct, 2016 08:08 pm
I would hope you would have more courage than that primary aged boy.

If she's such a hottie, she won't be free for long.
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Reply Sun 30 Oct, 2016 09:21 pm
You know what people regret the most? The lost opportunities they had and didn't take, the temptations they resisted for whatever reason and so on.
You'll regret it big time if you don't ask her out. Where there is no risk there is no gain. If you don't do it now she'll get snapped by someone else and then you'll come back and whine and whine.

So move your ass and get going!! Ask her out!
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