Andy if you're looking for the best way to get around that problem, buy a few disposable mascara wands and after you apply a couple of coats, run a clean brush over your eyelashes. It seperates them really well.
Also, I love these mascaras:
Cheap - Maybelline Full N' Soft (which is what I use pretty much every day)
More expensive (but definitely worth the money)
Kiss Me Mascara by Blinc. You can buy it at Sephora and it forms these little tubes around your eyelashes that don't come off even if you rub your eyes or go swimming or sweat or whatever -- don't buy the L'Oreal knock-off. Go with the real deal.
Bad Gal Blue by Benefit. This you can get either at Sephora, The Bay or Shopper's Drug Mart. It has a huge brush that defines really well and it's blue which a) adds a splash of colour if you don't really wear a lot of colour, and b) makes your eye colour really, really stand out.
I love makeup. Love it love it love it. I used to want to be a makeup artist, doing either high fashion or special effects. I have way too much of it -- the amount of money I've spent on makeup probably adds up to about $800. I'll post some pictures soon...
Also, one of my favourite quotes about makeup!
"I don't understand makeup, Gloria -- why wear it at all? Isn't it dishonest?"
"My dear, the reason we wear makeup is to prevent the world from seeing what we're like underneath."
"What's wrong with that?"
"What's wrong with that? My dear, if you allow your feelings to be exposed, people will hurt you with them. They will use your feelings against you. Something once private and sacred to you will be transformed into a weapon. Something precious will be damaged. You will experience pain."
--Douglas Coupland, The Gum Thief