I have recently made a wonderful new friend - we keep wondering how we didn't meet sooner when you look at just how similar we are. One point of difference though is our approach to money. I consider myself a fairly generous, sharing person. Over the past 5 years flatting with various people, I have never been the person that has polices food in the fridge (which I can completely understand, it's just not me) and my general philosophy is it all comes back to you in the end. Mutual sharing is what makes friendship so fun! Anyway, since new friend and I have been spending so much time together, I have noticed he is, for lack of a better word, scabby. He has drunken my gin on numerous occasions which would be fine except he keeps all of his to himself. I have shouted coffees every time we go out with no reciprocal gesture, he has used over half of our internet bandwidth on visits to download old movies he wants, and just the other weekend he turned up to my house after I had cooked a flat dinner, ate all the food, brought nothing and then left for town when a better offer came up. I don't know if he realizes that he's doing it, but I am feeling a little used and taken advantage of. How do I tell him to pay for his own sh-t without spoiling this great newish friendship? I really love hanging out with him, I just don't want to be the only one to pay for our fun. Suggestions please! J

I’ve got to be honest here, I can’t figure out if you’re that type that’s just super generous to a fault or a super generous person that keeps tabs.  The latter is always the worst kind, but I’ll give you the benefit of the doubt and assume you’re the former….in which case, you have a couple of options.  My advice would be to start mild and gradually build from there.

Step 1
It’s obviously easier to change your behavior than the behavior of someone else, so if I were you, J I’d scale back on your generosity.  I’m not saying take it all away, but for your own sanity I’d probably stop pimping out the free coffees all the time.  If you reel it in a bit, that might just open up the chance for him offer up the goods every now and then.  

Step 2
If you find that he’s still being a bit of a mooch - get a bit more direct.  Sarcasm and humor is always a good way to go.  For example, the next time you’re having people over for drinks say something to the effect of:  “Hey bud, BYOB because the last time your lush ass was over you sucked my stock up”  I mean, if he doesn’t get the hint then, see step 3.

Step 3
When you find a new friend, you kind of want to impress them because you want them to like you lots, right?  I get that, but the whole deal with a friendship is they’re supposed to improve the quality of your life.  You never want to feel bad around them, you know?   So when you do come across a deal breaking problem the best thing to do is to confront it.  I know it sucks to get real with a friend, but it doesn’t have to be some big ordeal.  Don’t beat around the bush, just be sensitive and honest in your approach.  I think if you said something to the effect of your last line to me, like  “we have the best time together, but lately I feel like I’ve been paying for all our fun times, and it’s starting to get a bit too much” it’s not too harsh.  Leave it at that and see what he says.  If he really is a good friend then he’ll step up.