My notebook

I have started using a small notebook (though I need to buy a smaller one that will fit in my back pocket), in which I plan to record my observations.

In layman's terms, I have to jot down the daft and weird stuff that people do, so I stop forgetting them.
I'll also be making stuff up about people in it. I shall explain...

I took my mum to an Italian restaurant this week, and decided to create a character sketch based on our lovely waiter. I know nothing of him, can't remember his name, and certainly didn't ask him about his life.
Today, three days after being there, he is now as follows:

His parents coddled and loved their child to the point of distraction, and as a result, our 19 year old hero still lives at home where his mother starches his shirts and makes his bed.
He is the grandson of a height challenged old woman, who lives in Rome and cleans at the Hilton Hotel.
His elder sister married a millionaire banker in Paris and has virtually abandoned her family because they embarrass her so much (it may have had something to do with her father crying in to his wine while trying to make a speech at her wedding. He basically threatened her husband with death should anything bad ever befall his beautiful daughter).
Our hero is single (because of the parents, no doubt) but has a good crowd of friends (male and female) who love him to pieces. Not enough to date him though.
He's good looking, lean (goes to the gym 3 nights a week), kind, thoughtful... everything that should land him the girl of his dreams. But alas, they all love him like a brother.

Now, what situation should I put him in that'll make for a good story?!