Well, so I'm pretty much wet-behind-the-ears when it comes to my bike skills but that didn't prevent me from trying to pass as many folks as possible during my last tri (Danskin Seattle) I didn't really even intend to kick it out on the road ride portion, but my competitive-ness got the better of me (and I wanted to see how fast I could go on I-90 when there aren't any cars around). Suprisingly, it was much easier to pace and pass in small spaces than I expected, and a lot of verbal communication helped loads in preventing any accidents, otherwise I may never have thought I could race other people.

So in response to question #1- I decided about 200 meters after I started pedaling the bike leg of the triathlon that I reallly really wanted to race it. I know that isn't a true bike race, but it made me want to get my skills solid so that I can in the future (Oh, and I finished 300th out of 4000 in the bike leg 154th overall, so that's not too shabby)

#2) No support, except for my boyfriend who bike-commutes with me.

#3) Sadly, I don't have any women to ride with

#4) I played soccer from ages 4-15 (to make me less shy, my parents said), b-ball from 7-12, started running competitively at age 12 thru 22 (and maybe again this year at 26)- so, yes, I think I'm pretty well steeped in competitive, aggressive sports, although I tend to be a quiet, mellow person otherwise.

#5) Main obstacles? I don't have anyone to ride with, and I'm a little concerned I'm not good enough with keeping control to ride with a group yet, nor do I know how to get started.... I imagine it's similar for a lot of women.