Alrighty, so I've been in a relationship for 2 and 1/2 years and last Sept I have become single again. I have kind of just been drifting around since than; mostly working and keeping busy with school (paramedic college) and I haven't really been on many dates since then. The problem is my friend wants to set me up with his girlfriend's friend (yea I know). She's attractive, nice and we have similar personalities. The only problem is I'm quite shy and frankly awkward in these "set-up" situations. I was just wondering if there was any helpful hints or tricks that anyone with knowledge in this situation might share. Much appreciated

If you have an interest in meeting her, maybe consider planning an activity where the four of you get together as a means of an introduction. You won't feel as much pressure to have to keep a conversation going alone and it won't feel as much like a set-up... more as just friends going out and having a good time.

Think of something fun where you can all be active. A movie, for example, doesn't really allow you to interact and get to know each other. If you both feel that it went well, then you can decide to do something just the two of you next time.

I have met her before, but I haven't really had any conversations, always just a quick comment or joke. I think I need something like a push in the right direction lol.
But what do you suggest as an activity; the only thing is where we live there isn't too much in the way of entertainment (a movie is considered a big chunk of it)

Perhaps a movie and dinner then. Go to the movie first, and that will give you another topic to talk about during dinner. Once you find out more of her interests, and if you are still interested in getting to know her better, you can plan some things around that. Does she like bike riding for example... take a ride to a park and have a picnic. Does she like hiking, fishing, or other outdoor activities? You might discover that she likes comedy or plays and you could take a longer date to someplace nearby for a show. Introduce her to something you enjoy so that you can teach her about it.

Focus on having fun, doing things you enjoy, and you'll find that you get back into the swing of things pretty quickly.

How and what did you do on dates when you were dating ? But be yourself, beyond all else.