The Expectation-Setting Conversation: A Step-by-Step Guide

Every casual arrangement has a "define the terms" moment. Sometimes it happens intentionally over coffee. Sometimes it happens accidentally during a text argument three months in when someone finally says "that's not what I signed up for."

The first version is better. This guide walks you through how to have the expectation-setting conversation proactively, clearly, and without making it feel like a business negotiation.

Before the Conversation

Get Clear With Yourself First

You can't communicate what you haven't figured out. Before sitting down with the other person, spend time thinking through:

What do I actually want from this arrangement? Be honest, not aspirational. If you want financial support, say so (to yourself, at least). If you want companionship without commitment, name it.
What are my non-negotiables? These are the things you won't flex on. Exclusivity or lack thereof. Financial terms. Frequency of contact. Privacy requirements.
What am I flexible about? Knowing where you have room to negotiate makes the conversation more productive.
What are my dealbreakers? Different from non-negotiables. These are the things the other person might want that would make the arrangement unworkable for you.

Write these down. Not to bring to the meeting like a legal brief, but to organize your own thinking.

Choose the Right Setting

This conversation deserves:

Privacy. Not in a crowded restaurant where you're whispering about allowance terms.
Sobriety. Save the wine for after. Clear heads make better agreements.
Enough time. Don't squeeze this into thirty minutes before someone has to leave. Budget at least an hour.
A neutral space. If possible, not in either person's home for a first conversation. A quiet cafe, a park bench, or even a video call can work.

The Conversation: Step by Step

Step 1: Set the Tone (5 minutes)

Open by acknowledging that this conversation might feel a little formal, and that's okay. Something like:

"I want us to be on the same page about what this looks like so we're both happy. This isn't about making rules — it's about making sure we both get what we're looking for."

This framing matters. It positions the conversation as collaborative rather than one person dictating terms.

Take turns describing what you're hoping the arrangement looks like. Cover:

The basics. What type of arrangement is this? Companionship? Friends with benefits? Sugar relationship? Mentorship? Something else?
Frequency and structure. How often do you envision meeting? What do typical interactions look like? See our detailed guide on scheduling and time commitments.
Communication style. How often and how do you expect to communicate between meetups?
Duration. Is this open-ended or time-bound? Do you see this lasting months, years, or is it a "let's see" situation?

The key here is that each person gets uninterrupted time to share. No rebuttals yet. Just listen.

Step 3: Identify Alignment and Gaps (15 minutes)

Now compare notes. You'll likely find three categories:

Full alignment: "We both want to meet weekly and keep things discreet." Great. Note these and move on.

Partial alignment: "We both want regular meetups but disagree on frequency." These need negotiation.

Misalignment: "One of us wants exclusivity and the other doesn't." These need careful discussion and might be dealbreakers.

Work through the partial alignments first. They're usually the easiest to resolve with compromise. Then tackle the misalignments honestly.

Step 4: Cover the Hard Topics (15 to 20 minutes)

These are the conversations people avoid. Don't.

Finances. If money is part of the arrangement, be explicit. How much, how often, what form, and what it covers. See setting financial expectations for detailed guidance.

Physical boundaries. What's on the table and what's not. This needs to be a clear, sober conversation — not something figured out in the moment.

Privacy and discretion. Who knows about this? What can be shared? What about social media? Our social media and privacy guide covers this in depth.

Exclusivity. Is this arrangement exclusive? Can either person see other people? Are there different rules for emotional versus physical connections?

Exit terms. How does this end if someone wants out? What does a respectful ending look like? Check out how to end an arrangement gracefully.

Step 5: Document the Essentials (10 minutes)

You don't need a contract. But writing down what you agreed to — even in a shared note or text exchange — prevents the "I thought we said..." conversations later.

At minimum, capture:

The nature and structure of the arrangement
Key boundaries and non-negotiables from both sides
Financial terms (if applicable)
Communication and scheduling expectations
Privacy agreements
How and when you'll check in on the arrangement

For more on why writing things down matters, see why you should write down your casual agreement.

Step 6: Schedule the First Check-In (2 minutes)

Before you wrap up, set a date — two to four weeks out — for your first regular check-in. This gives both people a built-in opportunity to revisit anything that isn't working once the arrangement is underway.

Expectation-Setting Checklist

Use this to prepare for and guide your conversation:

Common Mistakes in the Expectation Conversation

Being vague to avoid awkwardness. "We'll figure out the money stuff later" means someone's going to be disappointed. Specificity is kindness.

Agreeing to things you don't actually want. In the moment, it's easy to say yes to keep things moving. If you have reservations, say so. It's easier to negotiate now than to resent later.

Treating it as one-and-done. Expectations evolve. This conversation is the beginning, not the end. Build in regular opportunities to revisit and adjust.

Letting one person dominate. Both parties should speak roughly equally. If one person is doing 80 percent of the talking, pause and explicitly invite the other person's input.

What If the Conversation Reveals a Dealbreaker?

Sometimes you'll discover that what two people want is fundamentally incompatible. That's not a failure — it's the system working. Better to find out during a calm conversation than three months into an arrangement that's making someone miserable.

If you hit a true dealbreaker, acknowledge it honestly: "It sounds like we're looking for different things. I respect that, and I appreciate you being upfront about it."

Then decide together whether there's a modified version that could work for both of you, or whether it's better to part ways before things get complicated.

The expectation-setting conversation takes an hour. Skipping it costs months.