I am still alive, still busy with work. I am also in the middle of attempting to deal with... not a problem, exactly, but more of a situation. I ordinarily would not ask for advice about something like this, but the longer it goes on the more I know that I need to do something, and I am interested to get some extra opinions on this.

I normally have no issues with one of my roommates, but recently he has been having some difficulties paying rent and owes me several months of utilities. This roommate has been very generous with money in the past, especially when I was having financial issues, so the last thing I want to do is seem eager to be a "bill collector" of sorts. The problem is that the lack of utilities has been a bit of a financial strain for me and my other roommate currently. It is also not helping that he is not really looking for a new job, regardless of his belief that applying online to the same few places once or twice a week is "looking."

I do not need help regarding what to do -- I know exactly what I need to do. I need to talk to my roommate about this situation and make it clear that I would like him to actually go out for several hours each day, by bus if need be, to go find a job. In the meantime, he should be doing anything within his power to help around the house while I am at work, by doing things like cleaning and dishes.

The advice I need is in regard to how to do this. This is, of course, not an easy conversation to have. It also does not help that I am, for lack of a better term, a giant weenie. I hate confrontation of all kinds, and while I know I need to stand up for myself and make my thoughts known, I do not want to come across like a slave driver, or an angry parent, or what have you. I am also a little afraid that I will not be able to have a rational conversation, and if I get too emotionally charged, I might say or do something I will regret later. And this is not even looking into the future about what to do if worse comes to worse and things do not change.

I guess what I am asking is if anyone has ever had a similar experience that they might be willing to share when they had to do something like this? Any advice on how someone who is ordinarily a gigantic push-over can be assertive without being aggressive, or how to handle touchy topics like this with minimal damage to our friendship?