Lori has a roommate problem.

[Hauldren Collider]

Lori, you have to be assertive. You're not the *******, they are, now go and try and get your money.

Everyone in the thread is telling you the same thing.

[Lorizael]

Everyone in the thread is telling you the same thing.

I'm not like, surprised, that the response to "Lori has a roommate problem" is "Lori should talk to his roommates." I'm explaining why doing so is difficult for me. In the past, it's been very difficult for me to tread the line between being assertive and being an *******, which is why nowadays I tend to shy away from that line completely. I'm no longer on speaking terms with one of my brothers basically because trying to be direct but not confrontational is something I failed at spectacularly.

[Aeson]

I wish I could. It's there, but I'm simply unable to release it on strangers. You can ask my brothers, parents, friends, and ex-girlfriends if you need confirmation that my inner ******* is very real.

Clearly you need to date your delinquent roomates.

[C0ckney]

well you have two choices. you can either confront the problem and try to get your money or make excuses as to why you can't and lose it. you know what the right choice is, so make it.

this is actually the best possible situation for you to deal with treading the line, or whatever you want to call it, because you are 100% in the right here.

[onodera]

You send an email to people living in a room next to you? My friend had a roommate, an older woman, who was taking my friend's Ziploc bags to pick up her dog's ****. Instead of telling her to stop using the bags and buy her own, my friend wrote a note and put it in the drawer with the bags. It didn't work, because this kind of passive aggressiveness never works.

Just tell them they owe you money and ask when they will pay, bring the fourth mate with you if you're afraid.

[Hauldren Collider]

I'm not like, surprised, that the response to "Lori has a roommate problem" is "Lori should talk to his roommates." I'm explaining why doing so is difficult for me. In the past, it's been very difficult for me to tread the line between being assertive and being an *******, which is why nowadays I tend to shy away from that line completely. I'm no longer on speaking terms with one of my brothers basically because trying to be direct but not confrontational is something I failed at spectacularly.

You're moving out in a couple months. Who the **** cares? Go get your money. You're totally in the right.

[Lorizael]

I can easily imagine scenarios in which my roommates might believe I am not totally in the right. From their perspective, they moved in with the understanding that they would pay rent to the landlord, and then for some reason their roommates every once in awhile send out emails telling them they owe money for utilities that have been paid, even though those dudes never sat down with them and told them they also had to pay their share of the utilities.

I'm not saying this is a good reason why I shouldn't confront them or why they don't owe me money. I'm just saying that thoughts like this remind me that it is an inability/unwillingness to see things from other people's points of view that has gotten me in a lot of trouble in the past.

[rah]

Which should teach you that you should talk to roommates instead of using e-mails as your primary source of communication.
It's like texting people while in the same room with them. (which I could never understand, but then "GET OFF MY LAWN")

[Lorizael]

Oh, certainly. The only defense I have there is that we all have very different schedules and often aren't home at the same times.

[rah]

More the reason to do interactions face to face. Easier to com off non threatening in a one on one chat. And I've found it's easier to make someone feel shame for not holding up their side of obligations when they don't have a group of jackals to help support non compliance.

[Ben Kenobi]

It's nearing the end of the semester, and people are going their separate ways soon. I suspect that if I don't get the new roommates to pay me what they owe me very soon, I may lose the chance. Another water bill is due at the end of the month. I've sent an email out telling people what they owe me, and also telling them that one of them should pay the water bill since I handled the last one. I've yet to hear a response, which is typical.

So, what am I supposed to do here? How do I get these two schmucks to pay me what they owe me? It's not a huge amount (~$700 between the two of them), but for a poor jobless bum like me, it's more than I'd like to see simply disappear.

First things first.

One - hold a house meeting, with everyone present, you, the other legacy roomie, and both of the others.

Yes, I know you find verbalizing hard, but it would have been vastly easier to do this at the start of the year than at the end.

Also, 700 dollars is a LOT of money where I come from.

Given that it's the end of April, you are likely going to have to eat all of it. That's just reality. The only leverage you have is that you have a place to rent. without the place, there's nothing stopping them from leaving and stiffing you the bill.

If you're lucky you'll have roomies not willing to take that hit, but the reality is you have zero leverage except kindness and consideration on their part.

[Ben Kenobi]

it's been very difficult for me to tread the line between being assertive and being an *******,

Confrontation sucks, but is massively better than sucking up a 700 hundred dollar loss because you didn't set things up at the start.

[pchang]

Small claims court

Or judge Judy

Since you are too afraid of the alternatives, you are at your last resort.

[Lorizael]

I did take a former landlord to a landlord-tenant dispute court thingy a long time ago. That was fun.

[DaShi]

Geez Lori, how many people have to suggest break their fingers before you'll do it? They are never going to love you, so your only other alternative is fear.