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Iconic Fountain Pen?

Well, that is a good result. I like Esterbrooks. I would drool at the chance to pick-up one NOS. That was a great find.
 
The Easterbrooks are great pens for the money - make sure the nib isn't too fine, or they can be scratchy. Also, you may want to have the inc sac replaced as an original, unused ink sac could be quite brittle - lots of guys do this type of restoration work for very reasonable prices (swap out the old sac for a new one). The other issue with an Easterbrook is that if they are left unused for a while, they will gum up.

The Vanishing point, while I find hard to classify as iconic, is a great pen and at about $125 new, would be a great choice for a teenager because of its convenience factor. FYI, to those who may be interested in a VP, the nibs run narrow.

As for the Mont Blanc pens, while the 149 is nice, its also huge and I think that MB pens are way overpriced and, many of the examples I've handled aren't great writers - I'd take a Pelikan over a MB any day. But obviously, this is a personal preference.
 
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The is a Esterbrook company picture of the same pen, Mike can post the actual picture when he receives the pen today or tomorrow.
 
Unless the boy's expressed interest in fountain pens, I wouldn't bother buying him an iconic fountain pen.

Why should you? He won't appreciate it.

Buy him a good-quality, nice-looking fountain pen from a well-known manufacturer that won't break the bank. Show him how to use it and look after it and see what happens from there. No sense in buying the biggest and best if he doesn't even know the rest.
 
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