Casual Dating Expectations Checklist: What to Agree On Early

Casual dating sounds low-pressure by definition. But "casual" does not mean "undefined." In fact, the less committed a relationship is, the more important it becomes to clarify expectations upfront—because you cannot fall back on the assumptions that come with traditional labels like "boyfriend," "girlfriend," or "partner."

This checklist is designed for people in the early stages of a casual dating arrangement. You do not need to turn this into a formal contract. But you should have real conversations about each of these topics before you are three months in and discovering you have completely different ideas about what you are doing.

The Core Expectations Checklist

1. What Are We Actually Doing?

Start with the big picture. This is the conversation most people skip because it feels awkward, and it is the one that prevents 80% of casual dating disasters.

Have we both said out loud what we want from this? (Not hinted. Said.)
Are we on the same page about whether this could become more serious?
Have we defined what "casual" means for each of us specifically?
Are we both comfortable with the current label (or lack of one)?

Vagueness is not kindness here. Saying "let us just see where things go" when you already know you do not want a relationship is not keeping things light—it is withholding information the other person needs. For more on having this conversation without it getting weird, read How to Discuss Expectations Without Awkwardness.

2. Exclusivity and Other People

This is the number one source of conflict in casual dating. Do not assume.

Are we seeing other people?
Are we allowed to see other people?
Do we want to know about other people, or is do-not-ask-do-not-tell preferred?
If one of us starts developing feelings for someone else, how do we handle it?
Are there specific people (friends, exes) who would be off-limits?

We have a full article on this topic: Exclusivity Clauses: Agreeing on Whether You Can Date Others.

3. Communication Expectations

Different people have wildly different needs around communication, and mismatched expectations here can sink an otherwise good arrangement.

How often do we expect to hear from each other? Daily? A few times a week?
Is it okay to go a few days without texting?
Who usually initiates, and are we both okay with that pattern?
What platforms do we use to communicate? (See Choosing Communication Platforms)
Are late-night-only texts okay, or does that feel disrespectful?
How do we handle slow responses—is it fine or does it cause anxiety?

Check out our Communication Boundaries hub for deeper guidance on all of this.

Non-negotiable territory. These conversations should happen before physical intimacy, not after.

Have we discussed what we are both comfortable with physically?
Have we talked about sexual health, testing, and protection?
Do we both understand that consent is ongoing and can be withdrawn at any time?
Are there specific boundaries either of us wants to establish?
Have we discussed how to communicate during intimate moments if something is not working?

For a thorough guide, see Consent and Physical Boundaries in Casual Arrangements.

Casual dating gets complicated when other people get involved.

Do our friends know about this arrangement?
Are we comfortable being seen together in public?
How do we introduce each other? ("My friend"? First name only?)
Are we connected on social media? Should we be?
Are we posting about each other or keeping this offline?
What about family—is this something family members know about?

More on this in Social Media Boundaries in Arrangements and How Much to Share with Friends.

6. Time and Availability

How much of each other's lives are you actually in?

How often do we see each other? Is there a rough cadence?
Are weekday hangouts a thing, or is this weekends only?
Do we do "date" activities (dinner, movies), or is this more about staying in?
Is sleeping over expected, optional, or off the table?
How much advance notice do we give before wanting to see each other?
Are we available for last-minute plans, or do we need structure?

7. Financial Expectations

Even in casual dating, money comes up. Who pays for what?

Are we splitting things evenly?
Does one person tend to pay? Is that expected or just a pattern?
If there is a financial component to this arrangement, have we been specific about amounts and timing?
Are gifts expected, appreciated, or uncomfortable?
If we travel together, how do we split costs?

For arrangements with a financial component, How to Talk About Money in Arrangements is essential reading.

8. The Exit Plan

Nobody wants to talk about endings at the beginning. But casual arrangements end—that is kind of the point. Having a loose understanding of how you will handle it makes the ending far less painful.

Can either person end this at any time, no questions asked?
Do we owe each other a conversation, or is a text acceptable?
Is there a cooling-off period before we reach out again as friends?
What happens to shared belongings, photos, or messages?
Have we agreed to handle the ending with basic respect regardless of the reason?

Our Ending Arrangements hub covers this extensively, including Ending a Friends-With-Benefits Arrangement Without Losing the Friendship.

How to Use This Checklist

You do not need to sit down with a printed copy and go through it like a job interview. That would kill the mood and probably the arrangement.

Instead, use it as a conversation guide over your first few weeks. Bring things up naturally. "Hey, I wanted to check in about something" is a perfectly normal thing to say.

Some people prefer to put key points in writing—even a simple shared note on a phone works. Others prefer to just have the conversations and trust the understanding. Either approach is fine as long as both people feel heard.

If you want to formalize things a bit more, our guide on How to Structure a Casual Agreement walks you through the process without making it feel like a legal proceeding.

The One Rule That Matters Most

If you take nothing else from this checklist, take this: when in doubt, ask. The worst that happens is a slightly awkward 30-second conversation. The alternative—assuming and being wrong—can hurt real people and end something that could have been good.

Casual does not mean careless. It just means you are choosing flexibility over formality. And that flexibility works best when both people know exactly how much room they have to move.