Why and How to Schedule Regular Check-Ins for Your Arrangement

You wouldn't run a business without regular meetings. You wouldn't (hopefully) drive a car without ever checking the oil. So why do people enter casual arrangements and then never check in on whether things are actually working?

Regular check-ins are the single most effective tool for keeping an arrangement healthy. They're low-effort, high-impact, and they prevent the slow accumulation of resentment that kills most casual relationships.

What Is a Check-In, Exactly?

A check-in is a planned conversation where both parties in an arrangement step back from the day-to-day and assess how things are going. It's not a fight. It's not a performance review. It's a brief, structured conversation with a few simple goals:

Confirm what's working
Surface what isn't
Make adjustments before small issues become big ones
Reaffirm that both people are still happy with the arrangement

That's it. Fifteen to thirty minutes, on a regular cadence, with a simple format.

Why Check-Ins Matter More in Casual Arrangements

Formal relationships have built-in feedback mechanisms. You spend holidays with each other's families. You talk about the future. You have shared social structures that create accountability.

Casual arrangements usually don't have any of that. Without intentional check-ins, issues build silently. One person is dissatisfied but doesn't know how to bring it up. The other thinks everything's great. By the time the conversation finally happens, someone's already checked out.

Check-ins solve this by creating a regular, expected space for honesty. When both people know the conversation is coming, it lowers the barrier to raising concerns.

How Often Should You Check In?

This depends on the intensity and maturity of your arrangement:

New arrangements (first one to three months): Every two weeks. Things are still being established, and frequent check-ins help you catch misalignments early.

Established arrangements: Monthly is usually sufficient. You've settled into patterns and a monthly touchpoint keeps things on track.

High-intensity arrangements (living together, seeing each other multiple times per week): Weekly. The more intertwined your lives, the more surface area for friction.

Winding-down arrangements: Increase frequency temporarily. If one or both parties are reconsidering the arrangement, more frequent check-ins help manage the transition. See when to end a casual arrangement.

The Check-In Format

Keep it simple. Complexity kills consistency. Here's a format that works:

Round 1: The Good Stuff (3 to 5 minutes)

Each person shares one or two things that are going well. This matters. Starting with the positive sets a collaborative tone and reminds both people why the arrangement exists in the first place.

Examples:

"I really appreciated how you handled scheduling last week when things got hectic."
"I enjoy our Thursday dinners. They're a highlight of my week."
"I feel like our communication has gotten much better since we set those texting boundaries."

Round 2: The Adjustments (5 to 10 minutes)

Each person raises anything they'd like to tweak, change, or discuss. Frame these as requests, not complaints.

Instead of: "You never text me back on time." Try: "I'd love it if we could aim for same-day responses on texts. Would that work for you?"

Instead of: "The financial side of this isn't working." Try: "Can we revisit the financial terms? My situation has changed and I'd like to discuss adjustments."

Not every check-in will have adjustments. That's fine. The point is creating the space so that when something does need to change, there's a natural place to raise it.

Round 3: Looking Ahead (3 to 5 minutes)

Cover anything coming up that affects the arrangement:

Schedule changes or travel
Life events (job changes, moves, new commitments)
Plans you want to make together
Whether the overall direction still works for both people

Round 4: The Close (1 to 2 minutes)

End with a clear confirmation: "Are we both good? Anything else before we wrap up?" This gives one last opportunity to raise something and provides a clean ending.

Making Check-Ins a Habit

The hardest part isn't having the check-in — it's remembering to schedule it. Here's what works:

Put it on the calendar. Literally. A recurring calendar event takes thirty seconds to set up and removes the "when should we do this?" friction.

Tie it to an existing routine. After dinner on the first Sunday of the month. During your bi-weekly phone call. At the end of every third date. Anchoring it to something you already do makes it easier to maintain.

Alternate who leads. Taking turns ensures both people feel ownership of the process. The "leader" for that session is responsible for making sure the format is followed and both people get to speak.

Keep it conversational. You're not reading from a script. The format above is a guide, not a legal proceeding. Adapt it to your style.

Check-In Ground Rules

Agree on these upfront:

Both people speak without interruption during their turn
Phones are put away (unless you're doing the check-in by phone, obviously)
No bringing up check-in topics as ammunition in later arguments
If something raised needs more time, schedule a separate conversation
Either person can request an unscheduled check-in if something urgent comes up
Check-ins happen even when things are going well

That last one is critical. If you only check in when there's a problem, the check-in itself becomes associated with conflict. Keep doing them when everything's great so they stay neutral.

What If Your Partner Resists Check-Ins?

Some people hear "regular check-in" and think you're asking for couples therapy. Reframe it:

"I want to make sure we're both happy with how things are going."
"This is just a quick conversation every few weeks so nothing builds up."
"I'd rather spend fifteen minutes talking now than have a three-hour argument later."

If someone completely refuses to ever discuss how the arrangement is going, that's a yellow flag. Every healthy arrangement requires some degree of mutual feedback. Our article on signs of a one-sided agreement covers other warning signs.

Documenting Your Check-Ins

You don't need to take minutes. But after each check-in, it's worth jotting down:

Any specific changes you agreed to
New commitments either person made
Topics tabled for future discussion

A quick text summary ("Just to confirm — we agreed to move to monthly meetups and you'll handle the restaurant bookings") creates a shared record and prevents the classic "that's not what I thought we agreed to" problem.

For more on putting arrangements in writing, see why you should write down your casual agreement.

The Bottom Line

Check-ins aren't a sign that something's wrong. They're a sign that both people care enough about the arrangement to maintain it intentionally. Set the cadence, follow the format, and keep showing up — even when (especially when) everything seems fine.