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How to start dating in your late 20's?

Background: I'm 28. It's coming to the point where most of my friends are married/coupled up/have kids and I feel like I want someone too. I've never been in a real relationship. Aside from a high school boyfriend for a couple of months the closet thing I had was dating a guy on and off for a year that didn't want a relationship because I was a virgin (at 22). He strung me along and I was young and stupid. I sort of took that and ran with it and assumed most guys would take issue with that. Friends told me guys would care. Girl friends I knew had problems finding a guy who didn't run at the word virgin or inexperienced or were cautious about dating a woman who's never been in love.

I know I should have kicked myself in the butt years ago and dated but the fear stopped me and I'm also very shy when I meet new people. I know I should just put myself out there and do it, go out, or make a dating profile, deal with the rejections, but I just can't seem to get myself to do it. Another fear I have is I feel most guys in their late 20s/30s know what they want (in life and in relationships) and are established career wise and I'm still doing entry level admin jobs and taking night class for a certification because I finally figured out what I wanted to do after college.
How to start dating in your late 20's?
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