Assuming Instead of Asking: The #1 Arrangement Killer

If there's one piece of advice that could prevent the majority of arrangement failures, it's this: stop assuming, start asking.

Assumptions are silent. They live in the gap between what was discussed and what was imagined. And they're behind nearly every "but I thought we agreed..." argument that turns a good arrangement into a disaster.

The Anatomy of an Assumption

Assumptions in casual arrangements happen because people fill in blanks with their own expectations. When something isn't explicitly discussed, your brain fills in the answer based on:

• What you'd consider "normal" or "obvious"
• What you've experienced in past arrangements or relationships
• What you hope or fear will happen
• What you saw on social media, Reddit, or a friend's arrangement

The problem: the other person's brain is doing the same thing with completely different source material.

The 10 Most Dangerous Assumptions in Casual Arrangements

1. "We're obviously exclusive."

Unless the word "exclusive" was used in a conversation and both people agreed, you are not exclusive. Many people assume exclusivity because it's the default in traditional dating. In casual arrangements, it is not.

Ask instead: "Are we seeing other people? Are we okay with that? Do we want to know about it?"

2. "The financial terms will increase over time."

Some people enter arrangements expecting that an initial allowance will grow as the relationship deepens. That only happens if both people discuss and agree to it.

Ask instead: "Are these financial terms fixed, or will we revisit them periodically? Under what circumstances?"

3. "They know what I mean by 'casual.'"

"Casual" means radically different things to different people. For some, it means "no strings, just fun." For others, it means "a committed arrangement with clear limits on emotional involvement." For others still, it means "dating without a label."

Ask instead: "What does casual mean to you? What does it look like in practice? What's included and what's off the table?"

4. "They'll text me after we see each other."

Post-meetup communication norms vary widely. Some people send a "had a great time" text. Others don't contact again until the next scheduling conversation. Neither is wrong — unless one person expected the other.

Ask instead: "What does communication between meetups look like for you?"

5. "If something bothers them, they'll speak up."

Many people — especially those on the less powerful side of an arrangement — won't speak up about problems because they're afraid of consequences. They'll suffer in silence, build resentment, and eventually disappear or explode.

Ask instead: "Is there anything about our arrangement you'd change? I genuinely want to hear it." Then prove you mean it by listening without defensiveness.

6. "We agree on what 'availability' means."

"I'll be available for meetups" could mean anything from "I'll clear my schedule whenever you ask" to "I'll try to fit you in when I can." The gap between those interpretations is enormous.

Ask instead: "How many times per month are we aiming for? How much advance notice do we need? What happens when scheduling conflicts come up?"

7. "Gifts come with no expectations."

Sometimes gifts are just gifts. Other times, they carry implicit expectations about gratitude, reciprocity, or continued participation. If you're not sure which it is, assume nothing and ask.

Ask instead: "When you give me something, is that a gift with no strings, or is there an expectation attached?"

8. "They're happy with how things are going."

Silence isn't satisfaction. Many people go through the motions of an arrangement that isn't working because they don't know how to raise the issue. Regular check-in conversations exist specifically to surface what people wouldn't volunteer.

Ask instead: "How are you feeling about our arrangement? Scale of 1-10, where are you?"

9. "We'll figure out the ending when we get there."

This assumption is so common and so destructive that we wrote an entire article about it: Ignoring the Exit Plan. The time to plan for an ending is before it happens, not during.

10. "They understand my boundaries."

Just because a boundary seems obvious to you doesn't mean the other person shares it. "Don't contact me at work" or "don't tell your friends about us" or "don't take photos of me" are boundaries that need to be stated, not assumed.

Ask instead: "What are your non-negotiable boundaries? Here are mine."

Why People Assume Instead of Asking

Understanding the psychology helps you fight the instinct:

Fear of seeming needy or high-maintenance. Asking questions can feel like you're demanding too much. In reality, it shows maturity and respect for the arrangement.

Desire to keep things "easy." Detailed conversations feel like they kill the spontaneity. In practice, they enable it — when the basics are settled, you can actually relax and enjoy each other's company.

Avoidance of awkward topics. Money, exclusivity, intimacy boundaries, exit plans — these conversations are uncomfortable. But they're less uncomfortable than the fights that happen when assumptions collide.

Overconfidence in shared understanding. "We're so compatible, we're definitely on the same page." Maybe. But you won't know until you check.

The Fix: An Assumption Audit

Try this exercise, either on your own or with your arrangement partner:

1. List everything you believe about the arrangement — frequency, financial terms, exclusivity, communication norms, boundaries, future expectations, ending procedures.

2. Mark each item as either "explicitly discussed and agreed upon" or "I'm assuming this."

3. For every assumption, initiate a conversation. It can be as simple as: "I realized we never actually discussed [topic]. What are your thoughts?"

4. Write down the answers. Assumptions only stay resolved if they're documented.

You might be surprised how many "obvious" things were never actually discussed.

What to Do When Assumptions Have Already Caused Damage

If an assumption has already led to a misunderstanding or conflict:

1. Own it. "I assumed X, and I realize now we never actually discussed it. That's on me."
2. Don't blame the other person for not reading your mind.
3. Have the conversation now. Better late than never.
4. Agree on the actual terms going forward and write them down.
5. Use it as a learning moment. What other assumptions might be lurking?

For more on resolving conflicts that arise from miscommunication, read How to Handle Disagreements Without Blowing Up.

The Bottom Line

Every assumption is a conversation you didn't have. Every conversation you didn't have is a future conflict waiting to happen. The most successful casual arrangements aren't the ones between the most compatible people — they're the ones where both people had the courage to ask the awkward questions early.

Start asking. Today.

For more on avoiding common arrangement pitfalls, visit our Common Pitfalls hub.