Yes, I'd fly it. Yes, I'd log it. And yes, I'd have fun doing it. This bullcrap about flight time being deemed "compensation" is exactly why I don't want the government in charge of my healthcare (not trying to turn this into a political thread hijack). I'd like to meet the clown at the FAA who came up with that nonsense. The intent of the reg is to keep people from profiting from their flying w/o a commercial ticket. Man, if lawyers were in charge of moving airplanes, not a single flight would ever take off. The purpose of logging flight time is to keep track of FAA-required currency. How the hell is that compensation? By that logic, it'd be illegal to accept an aviation scholarship for advanced flight training, since you're paying less that the pro-rated share, as is also the case if someone has their parents pay for some or all of their expenses. Oh, and if you can't log the time, then I guess you can't gain experience and learn from your mistakes as a PPL, because that's also "compensation". Gimmie a freaking break! That said, at least take your friend with you and pitch in half the cost of fuel, oil, and whatever else the reg says you have to "share" expenses for. Also, I don't remember reading that you necessarily have to pay using money--surely you can buy your friend multiple rounds of beer and call it even. However, I probably wouldn't leave a paper trail that shows he charged everything to his credit card, and thus you have no means to prove that you "shared" the expenses with him. And do yourself a favor--don't give the FAA any reason down the road to dig deeper into the private affairs of you and your friend.