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The money questions
Money is the number one source of roommate conflict, so these come first, even though they feel like the most awkward. You want to know, before anyone signs, that the rent fits their budget comfortably, how they expect bills to be split, and how they think about the deposit. Vague answers here are the loudest roommate red flag there is.
Ask these out loud: What's your budget, and does this rent fit it comfortably? How do you want to split bills, evenly or by usage? Are you comfortable settling up on a fixed date each month? How do you want to handle the deposit and the one-time move-in costs? The fair ways to actually divide rent are covered in how to split rent with roommates, so you can agree on a method, not just a vibe.
- What's your budget, and does this rent fit it comfortably?
- How do you want to split bills — evenly, or by usage?
- Are you okay settling up on a fixed date each month?
- How should we handle the deposit and one-time move-in costs?
- Have you ever had a rent or bills problem with a past roommate?
The lifestyle questions
These decide whether you'll actually enjoy living together. The goal isn't to find someone identical, it's to find the mismatches that matter to you specifically. If you work early, their idea of quiet hours matters more than almost anything; if you cook constantly, kitchen habits do.
Ask about the daily rhythm and the friction points: What's your work and sleep schedule? How often do you have guests, and how do you feel about overnight stays or a partner being around? How clean is clean, to you? Do you smoke, and where? How do you split or share groceries? Their answers map straight onto the house rules you'll want to set, so listen for where your normals differ, not where they match.
The logistics questions
The boring questions prevent the expensive surprises. You need the practical facts lined up before you commit: how long the lease runs, when they can actually move in, whether there are pets, and who owns the furniture. A roommate who wants a six-month lease when you want two years is a mismatch worth knowing now, not in month five.
Cover: How long do you want the lease to be? When can you move in? Do you have pets, or want to get one? What furniture are you bringing, and what's shared? Are you on the lease, or subletting? Getting these on the table early means the roommate agreement you write later is just confirming what you already discussed, not negotiating from scratch under time pressure.
Turn the answers into something you both agreed to
A good conversation that lives only in memory isn't worth much three months later, when one of you remembers it differently. Once the answers line up, write the important ones down: the rent split, the deposit, notice periods, and the day-to-day house rules. A one-page roommate agreement handles the money and exit terms; house rules handle the daily stuff.
From there, the goal is to keep what you agreed visible so it actually holds. Homies keeps the shared money and chores in one place the whole house can see, every expense on one running balance, the chore rotation laid out, the grocery list shared, so the things you asked about up front don't quietly drift once you're living it. It's a whole-home roommate app for iPhone and Android, in closed beta, free while we build it, with one signup for the whole home.
Frequently asked questions
What's the most important question to ask a potential roommate?
Whether the rent and bills fit their budget comfortably, and how they want to split them. Money is the number one source of roommate conflict, so a clear, specific answer here tells you more about the next year than almost anything else. Vagueness about money is the warning sign worth taking seriously.
How do I ask a roommate about money without it being awkward?
Frame it as logistics, not interrogation: 'How do you like to split bills and settle up?' is a normal planning question, not a personal one. Asking it openly also signals that you take the shared money seriously — which is exactly the kind of roommate most people want. Anyone reasonable expects these questions.
What answers should be red flags?
Evasiveness about budget or how bills get split, pressure to commit before you've met or seen the place, and a story where every past roommate was 'crazy.' Habits like a different schedule or cleanliness level are usually solvable; dishonesty and dodginess about money are the answers that predict real trouble.
Should we put what we agreed in writing?
Yes. A conversation you both remember differently in month three causes the exact conflict you were trying to avoid. A one-page roommate agreement captures the rent split, deposit, and notice periods, and house rules capture the daily stuff — so you're confirming what you discussed, not renegotiating under pressure.
Is there an app to manage things once we actually live together?
Yes. Homies keeps the shared money and chores visible to the whole house: one running balance for every expense, a chore rotation, and a shared grocery list, so what you agreed up front doesn't drift. It's a whole-home app for iOS and Android, in closed beta — join now to get in while it's early and free.
Let Homies keep score for you
What these guides set up by hand, the app runs on its own: the chore chart fills itself, balances settle in a tap, and the shopping list stays current for everyone. Homies is in closed beta now: join and you're in early, free while we build it.