Okay... I really just need to vent and get some good advice. Here is the story: My good friend's boyfriend is really getting on my nerves. Apparently he is extremely clueless or just plain cheap! And I just don't know what to do anymore. Last night, we went out for dinner and then afterwards for drinks. At dinner, he orders two beers (total $10 for both) and a meal ($10). My friend and I SPLIT an appetizer platter ($10) and just got waters with lemon. The bill comes. So not factoring in the meal tax or tip, her boyfriend pulls a $20 bill out of his wallet and plops it on the table as if he's saving the day! And then he says, "Oh, here" and pulls out another one dollar bill. That should cover it. Yeah, right! I ended up putting in $9 for what should have been less than that but I didn't want the poor waiter to go without a good tip, and my friend put in more than that! It seems like she is always covering for this guy! This is not an isolated incident, it occurs a lot. And right now, I am trying to save some extra cash. And wait, it gets better. We go to a pub after, and get some drinks. I make my order of the cheapest $1.50 drink special (because I am trying to save money right now) and he gets the $4.50 bottle of imported beer! And has the nerve not to take out any $ under the assumption that since I first placed the order, the first round is on me. I was too shy to ask for any money so I paid that and the tip. He didn't offer anything. And now this really boils my blood.... He asks his girlfriend a little while later what she wants to drink and DID NOT even ASK me!!!!! So he got the next round for just himself after I just bought his beer and didn't even get another one for me! What the heck!!!! As you can tell I am just so mad right now. I didn't know how to say something to him without ruining the evening or feeling awkward. What do I do in the future? I dont' want to keep paying for this guy when we all go out! Thanks in advance!