It wouldn't surprise me if Charles somehow contacts Des asking for help protecting his daughter!
(Or maybe the bathroom scene where he gave Des her phone number WAS a way to involve him!)

I knew right away, that Desmond will protect Penny in the future after the escape the island. The only flaw is if Desmond never gets off the island or dies.

Oh, I love the idea that the bathroom scene was part of Widmore's plan to try and protect Penny! He offered Desmond the money before and knows that nothing wil keep Desmond from her.

this sets up a possible completion to part of desmond's story arc, that is widmore's disdain of him as a coward not worthy of his daughter (also his own self disdain). if penny survives ben my bet is it'll be due to desmond, putting widmore forever in his debt and finally shaking off the cowardice tag.

all these arcs coming together... it's gonna be very interesting any way it turns out.

I always wondered if Widmore had a hand in getting Desmond to the island (thru being given 'The Elizabeth') to keep him away from Penny. Now I'm wondering if Widmore got Desmond to the island to save Penny.

I'm not sure how relevant it is to the whole Desmond-Charles story but I just watched the first episode of Season 4 again and saw something I had missed the first few times. When we see another clip of Charlie warning Des about "Not Pennys Boat" he reads the message and says something.
Now, I believe that it looks like he is saying "Widmore"?
If so, then perhaps Desmond knows more about Charles' plans than he has let on. E.g. Was Des working with Charles to find the island in order to win over Charles for Penny?
Ok, I'm not sure on the why bit but I would interested to see if anyone else can see the same lipping from Desmond!

Ok, I'm not sure on the why bit but I would interested to see if anyone else can see the same lipping from Desmond!

Not sure where the clip is on 401, but i looked at TTLG and he just reads the message out loud - 'not penny's boat'. with the scottish accent 'boat' is pronounced almost to rhyme with 'more', that is, the 't' is silent. so it kind of looks like he might be saying 'widmore'.

I knew right away, that Desmond will protect Penny in the future after the escape the island. The only flaw is if Desmond never gets off the island or dies.

Who's to say that Penny finds the island and stays with Des, after Des kills her father when she finds out how powerful and corrupt he is. Therefore, Ben could ultimately have what he wants (The death of a Widmore), and game over.

Lost Wooky you could very well be right. I wasn't sure, at first I thought he was just reading out loud but the more I watched it the more it didn't fit. Probably just a case of me willing it to be something!