Always a good idea.
I'm right there with you on being uncomfortable asking others... but its one of those things that we, as photographers, have to deal with if we are going to venture into portrait photography.
If you don't have their face in the picture, you don't need a model release.
If you're doing general shots and people are in them (like kids playing at a park but you're not focusing on any certain one), then I would say you don't have to explain yourself, but be ready (its always handy to have a card or be willing to get rid of their pictures).
Flattery only works with certain types of people. Don't act like you're coming on to them. Just strike up a conversation (you can use small talk, if you're into that sort of thing), or just ask them if they wouldn't mind giving you a second to help further your hobby/career. ALWAYS offer proofs and let them know your full intentions! Setting up an e-mail strictly for this purpose is a great idea, especially if they have questions later. But do always have a model release handy. Hey, if they don't oblige to sign it, you're still getting some practice in!
Bottom line, unless you're psychic (chances are... you're not), you'll never know what they're going to say until you ask. I know, I know... easier said than done... but just try putting yourself in their shoes and approach them how you'd like to be approached. <- Though, strike that last remark if you're into bad lines and cheesy come-ons! : )
Good luck! Remember, there are plenty of us out there that feel your pain!
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