Running tends to be torture for me and I do not enjoy it, but I'm committed to completing a triathlon this summer, thus I've done what I can to make it bearable. The only tip I can give is that shoes really matter when it comes to running and the way you specifically run may affect which shoes are right for you, regardless of how good they seem to fit. I would suggest going to a running specific store and be prepared to spend around $100 on a nice pair of shoes with a proper fit (I had a salesman who took the time to analyze me running on a treadmill and selected shoes based on his analysis). I still don't enjoy running, but it isn't near as bad since I found the right shoes.