Conflict Prevention Tools

Most conflicts in casual arrangements are preventable. They come from skipped conversations, not genuine disagreements. These tools help you identify friction points early and address them before they escalate.

Conflict Prevention Checklist

A comprehensive pre-flight checklist for casual arrangements. If you can check every box, you've addressed the most common failure points. Unchecked items tell you exactly which conversations still need to happen.

Use this before finalizing any arrangement. Go through each section together. Unchecked items aren't failures—they're unfinished conversations.

Revisit this checklist after the first month and again quarterly. Items that were checked initially sometimes unravel as circumstances change.

Pre-arrangement readiness check:

0/9 completed
CONFLICT PREVENTION CHECKLIST ============================== Date: _______________ Completed by: [ ] Person A [ ] Person B [ ] Both BEFORE STARTING THE ARRANGEMENT [ ] We have each stated what we're looking for in plain terms [ ] We have discussed and agreed on financial terms (if applicable) [ ] We have identified our hard boundaries and shared them [ ] We have agreed on communication frequency and channels [ ] We have discussed relationship expectations explicitly [ ] We have talked about what happens if one of us wants to end things DURING THE ARRANGEMENT [ ] We have a scheduled time to check in on how things are going [ ] We know how to raise concerns without it feeling like an attack [ ] We have agreed on how to handle changed circumstances [ ] Neither of us is relying on assumptions about the other's feelings [ ] We have a written record of our key terms (even informal notes count) PRIVACY & SAFETY [ ] We have agreed on what personal information is shared vs. private [ ] We have discussed photo/message storage and deletion policies [ ] We have a plan for what happens with shared information if we part ways [ ] Both of us feel physically and emotionally safe in this arrangement RED FLAGS TO WATCH FOR If any of these appear, pause and re-evaluate: [ ] One person consistently avoids discussing terms in writing [ ] Agreed-upon terms keep changing without mutual conversation [ ] One person feels unable to bring up concerns [ ] Financial terms are vague or shifting [ ] One person discourages the other from telling anyone about the arrangement [ ] Boundaries that were agreed upon are being tested or ignored

Difficult Conversation Planner

A structured framework for planning a conversation about something that's not working. Helps you define the issue, plan your words, and anticipate responses—so the conversation stays productive instead of escalating.

Fill this out before the conversation, not during. The goal is to enter the discussion knowing what you want to say, what outcome you're seeking, and how you'll handle different responses.

Focus on “I” statements and specific examples. “I've noticed the last two payments were late” is more productive than “You never pay on time.”

DIFFICULT CONVERSATION PLANNER ================================ Date: _______________ Planned by: _______________ STEP 1: DEFINE THE ISSUE What specifically is bothering me? (Be concrete — "I feel undervalued" is less useful than "The last two payments were late without explanation.") _______________________________________________ _______________________________________________ When did this start? _______________________________________________ How many times has it happened? [ ] Once [ ] A few times [ ] It's a pattern STEP 2: CHECK YOUR GOAL What outcome do I want from this conversation? [ ] Acknowledgment that the issue exists [ ] A specific change in behavior [ ] Renegotiation of terms [ ] To understand their perspective [ ] To end the arrangement [ ] Other: _______________________________________________ Am I open to hearing their side? [ ] Yes [ ] Mostly [ ] I've already decided STEP 3: PLAN YOUR OPENING Use "I" statements. Avoid blame language. Instead of: "You always _______________" Try: "I've noticed _______________ and I want to talk about it." Instead of: "You never _______________" Try: "It matters to me that _______________ and lately it hasn't been happening." My planned opening: _______________________________________________ _______________________________________________ STEP 4: ANTICIPATE THEIR RESPONSE What might they say? _______________________________________________ How will I respond if they get defensive? _______________________________________________ How will I respond if they dismiss the concern? _______________________________________________ What's my bottom line? (At what point do I walk away?) _______________________________________________ STEP 5: LOGISTICS When will I bring this up? [ ] At our next meeting [ ] Over a call [ ] Via message first Setting: [ ] Private (their place or mine) [ ] Public (restaurant, café) [ ] Remote Do I need time after the conversation to process? [ ] Yes — I'll plan for _______________ [ ] No

Before starting the conversation, confirm:

  • You've identified the specific issue (not a vague feeling).
  • You know what outcome you want.
  • You're prepared for them to disagree or get defensive.
  • You have a bottom line—the point where you'd end the arrangement if the issue isn't addressed.
  • You've chosen an appropriate time and setting (not when either person is stressed or rushed).

Red Flag Assessment

A scored self-assessment that helps you objectively evaluate whether concerning patterns exist in your arrangement. Removes the guesswork from 'Is this normal?' by providing concrete indicators and thresholds.

RED FLAG ASSESSMENT ==================== Date: _______________ Completed by: _______________ Rate each item from 0 to 3: 0 = Not happening 1 = Has happened once or mildly 2 = Happens occasionally or noticeably 3 = Happens regularly or severely COMMUNICATION RED FLAGS ___ Avoids putting agreements in writing ___ Changes terms verbally and denies the original version ___ Responds with anger or silence when concerns are raised ___ Uses guilt to end disagreements ___ Goes silent for extended periods without explanation FINANCIAL RED FLAGS ___ Support amounts shift without discussion ___ Support is withheld as punishment or leverage ___ New financial expectations appear without prior agreement ___ One party controls all financial decisions ___ Financial terms are described as "generous" to shut down discussion BOUNDARY RED FLAGS ___ Boundaries agreed upon are repeatedly tested ___ "Jokes" are used to push past stated limits ___ Privacy terms are violated (telling others, sharing photos) ___ One party pressures the other to share more than agreed ___ Consent is treated as a one-time event rather than ongoing POWER DYNAMIC RED FLAGS ___ One person makes all scheduling decisions ___ One person's preferences consistently override the other's ___ "I do so much for you" is used to win arguments ___ One party feels unable to say no without consequences ___ Ending the arrangement feels unsafe or financially devastating SCORING 0–5: Low concern. Continue with normal check-ins. 6–12: Moderate concern. Have a direct conversation about specific items and consider using the Difficult Conversation Planner. 13–20: Serious concern. Consider whether this arrangement is healthy for both parties. Consult a trusted friend or professional. 21+: Critical concern. Prioritize your safety and well-being. Consider ending the arrangement with support from a trusted third party. YOUR TOTAL: _______________ Items scoring 2 or 3 that need immediate attention: 1. _______________________________________________ 2. _______________________________________________ 3. _______________________________________________

Honest questions to ask yourself:

  • Am I scoring items low because they genuinely aren't happening, or because I'm minimizing them?
  • Would a trusted friend agree with my scores if they saw how things actually work?
  • Are there items I scored as 1 that have been slowly increasing over time?
  • If the roles were reversed, would I think these scores were acceptable?

Written clarity prevents friction: The majority of arrangement conflicts stem from conversations that never happened. Each unchecked box on these tools represents a potential misunderstanding waiting to surface. Addressing them now takes a fraction of the effort that resolving them later requires.

Many conflicts start with misaligned expectations. The Expectation Alignment Worksheet can help surface those gaps before they become problems.