When I was a kid my mother always used to say to me "go ask, all they can do is say no..." I have kept that little aphorism in my head most of my adult life. Really, it's a very positive little piece of advice. It has rarely gotten me into trouble and it often helps me and opens doors I never would expect to be open.
Here is a nice little example of that advice in action:
Last week I was up late with my usual insomnia and I decided to kill some time surfing eBay. I went through my saved searches and while I was checking out Gary Carter cards, I saw he was featured on Allen and Ginter rip cards this year. The couple that I saw were pretty cool, so I started narrowing my searches down. One thing I do like to do with my favorite players is see if their uniform numbers are available. After plugging in "08" I didn't find anything, so I checked the completed items. I saw that about a month ago, indeed a number 08/25 was posted with an outrageous buy it now price. I clicked on it and also saw that it hadn't sold. So I dropped the seller a line and asked him about the card and asked if it was still available. He got back to me right away (he must be an insomniac too) and told me he decided to rip it. I told him, oh, that's cool, and asked him what he got inside. He gushed proudly that he got a redemption for a game used piece. We pleasantly emailed back and forth a few more times and I got around to asking what he would want for the ripped card. He told me, well, I guess $20 would do the trick. Now, I had seen other ripped Carter cards going for $25-$30-plus that a) weren't serial numbered 08 b) had him on the Expos and not the Mets and c) had the usual exorbitant shipping costs. I very politely told him yes and silently squealed with glee as I sent him the money via paypal. I think my friendly demeanor and interest in what he had pulled from it softened him up. That or he was just a very polite dude. Either way, he securely mailed it right away and now this tremendous card is mine.
tl;dr - I scored this awesome Gary Carter card for $20 by asking about it and being polite.