The First Conversation Checklist: What to Cover Before You Agree

The first real conversation about your arrangement is the most important one you will have. It sets the foundation for everything that follows. Miss something critical, and you will spend the next three months dealing with the fallout.

This checklist covers every topic you should discuss before committing to a casual arrangement. You do not need to cover all of these in a single sitting—in fact, it is better if you do not (see How to Discuss Expectations Without It Being Awkward). But every item on this list should be addressed before you consider yourselves "in an arrangement."

The Nature of the Arrangement

Start with the big picture. These questions establish what you are actually building.

What type of arrangement is this? Casual dating, companionship, mentoring, friends with benefits, sugar relationship, or something else entirely?
What are each person's primary motivations? Why does each person want this arrangement? What are they looking for that they are not getting elsewhere?
Is this exclusive or non-exclusive? Can either person see other people? If so, are there any restrictions (different gender only, no mutual friends, etc.)?
What is the intended duration? Open-ended, a specific number of months, or "let us see how it goes with check-ins"?
What is this NOT? Sometimes defining what the arrangement is not is as important as defining what it is. If this is not heading toward a traditional relationship, say so clearly.

Financial Terms

If money is part of the arrangement—in any form—this section is non-negotiable. Leaving financial terms vague is the number one predictor of arrangement failure. See How to Talk About Money in Casual Arrangements for detailed guidance.

Is there a financial component? Be direct about whether money, gifts, or expense-sharing is part of the deal.
What form does it take? Regular allowance, per-meeting amount, gifts, paid expenses, or some combination? See Allowance vs. Gifts vs. Shared Expenses for the differences.
What are the specific amounts? Vague terms like "generous" mean different things to different people. Use numbers.
When and how is financial support provided? Beginning of the month, after each meeting, on request? Via cash, Venmo, bank transfer?
Under what conditions does financial support change or stop? If one person cancels a meeting, does the financial arrangement change? What about holidays or vacations?

Time and Availability

How much of each other's time you expect to occupy is one of the most frequent sources of conflict. Get specific. Read more at Setting Boundaries Around Time and Availability.

How often will you meet? Weekly, biweekly, monthly? A specific number or a range?
What days and times work? Are there specific days that are always off-limits?
How long are typical meetups? A few hours, a full evening, overnight?
Who plans and initiates? Is one person always the planner, or do you alternate?
How do you communicate between meetings? Daily texts? Weekly calls? Only to make plans?
What are expectations around response times? Is a same-day response expected, or is more flexibility okay?

Boundaries and Comfort Levels

This is where you discuss what each person is and is not comfortable with. Do not assume anything.

Physical boundaries. What level of physical intimacy is expected? What is off-limits?
Emotional boundaries. How emotionally invested are you both expecting to become?
Social boundaries. Will you attend events together? Meet each other's friends? Appear in public in certain places?
Digital boundaries. Can you text each other on personal phones? Are video calls okay? What about social media connections?
Geographic boundaries. Are meetings at homes, hotels, restaurants, or other specific locations?

Privacy and Confidentiality

Privacy should not be an afterthought. Cover these items explicitly.

What information is confidential? Names, financial terms, details of the arrangement, personal background—specify what stays private. See What Is a Confidentiality Clause?.
Who can know about the arrangement? Can you tell a close friend? A therapist? Nobody at all?
What are the social media rules? No posts, no tags, no check-ins at shared locations—or something more relaxed?
How do you handle digital privacy? Which messaging platform? What about photos?
What happens if privacy is breached? Discuss the consequences and response plan before you need one.

Health and Safety

These topics are personal and can feel intrusive, but they are essential for both people's wellbeing.

Sexual health. Testing status, barrier use expectations, and how often to re-test.
Safety check-ins. Should either person share their location with a trusted friend during meetings?
Substances. Are there expectations around alcohol or drug use during meetings?
Emergency contacts. Does each person know who to contact if something goes wrong?

Conflict Resolution

Disagreements will happen. Having a framework in place before they do prevents escalation.

How do you handle disagreements? Direct conversation, cool-off period, written messages, or a combination?
Is there a check-in schedule? Monthly reviews of the arrangement can catch issues early. See What to Do When Expectations Change Mid-Arrangement.
What are the deal-breakers? What would cause either person to end the arrangement immediately?

Exit Terms

Nobody likes talking about endings at the beginning. But this is one of the most important sections of your arrangement. See How to End an Arrangement Gracefully and What a Good Exit Clause Should Include.

How does either person end the arrangement? A conversation, a written notice, a specific notice period?
What happens to financial commitments when it ends? Is there a final payment? What about outstanding expenses?
What happens to shared information? Are messages deleted? Photos destroyed? Confidentiality maintained indefinitely?
Is there a no-contact period after ending? Some people prefer a clean break. Others want to remain friendly. Discuss this in advance.

How to Use This Checklist

Before the conversation: Read through the checklist yourself and mark which items are most important to you. Note your own positions on each topic.

During the conversation: Work through the topics that matter most first. You do not need to follow the checklist in order—start with whatever feels most natural and important.

After the conversation: Document what you agreed on. A simple shared document with your answers to each relevant item is enough. This becomes the foundation of your written agreement.

Periodically: Return to this checklist every month or quarter. Are the answers still accurate? Has anything changed? Use it as a check-in tool, not just a one-time exercise.

What If the Other Person Resists the Checklist?

Some people will see a structured approach as a sign that you are "too serious" or "overthinking it." Here is how to handle that:

Explain the benefit. "I have seen arrangements go sideways because people did not get on the same page upfront. This protects both of us."
Be flexible on format. The checklist does not need to be a formal document. It can be a casual conversation guided by these topics.
Pay attention to what they resist. If someone refuses to discuss financial terms clearly or pushes back against privacy agreements, that is informative. Resistance to specific topics often means those are exactly the topics where expectations diverge.

The Bottom Line

The first conversation sets the tone for the entire arrangement. Taking the time to cover these topics—even imperfectly—puts you miles ahead of the vast majority of casual arrangements that run on assumptions and good intentions.

No checklist can guarantee a perfect arrangement. But it can guarantee that you start with your eyes open, your expectations aligned, and your boundaries clear. That is the best foundation you can build.