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I started with Couch to 5K, and then went on to Marathoning for Mortals.
The shoes are the most important thing, and obviously good socks and a sports bra. I wouldn't, at this point, invest in any fancy clothing or heart rate monitors or anything like that.
How to choose your first 5K? I would look for something that is timed with a chip, not too crowded, and a relatively flat course. If you are in a major city, there are probably tons of them.
Personally, I hate running with music, but if it helps you train, that's cool. Just be careful when you are running outside to remain aware of your surroundings. Some races discourage you wearing ipods on race day.
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