Situationships can be tricky, right? You’re in that space where things are more than just casual but not quite a full-blown relationship.
It’s that in-between phase where you might be wondering what comes next or even if there is a “next.”
Whether you’re trying to figure out where you stand, what the future holds, or just want to ensure you’re on the same page, having some thoughtful questions in your back pocket can help clear the air.
Table of Contents
Defining the Relationship
- Do you see this as more than just a casual thing?
- What are your thoughts on labels like boyfriend or girlfriend?
- Do you think we should define what this is, or are you happy with how things are?
- Are you seeing other people right now?
- How do you feel about the idea of us being exclusive?
- What do you tell your friends about us?
- Do you feel like we’re on the same page with what this is?
- Are you comfortable with how things are between us?
- Is there anything you wish was different about our dynamic?
- Do you feel like we’re more than just friends?
- Are there any topics we haven’t discussed yet that you think we should?
- How would you feel if one of us started seeing someone else?
- Do you believe this could turn into something more serious?
- Would you be upset if I called this a relationship in front of others?
- Do you think our connection is just for fun, or could it be something more?
Emotional Involvement and Commitment
- What are your feelings towards me?
- Are there feelings you have here that you haven’t felt before?
- Do you feel like you can be your true self with me?
- Are there things you feel you can’t tell me?
- Do you feel emotionally fulfilled with me?
- Have you ever thought about what would happen if things got more serious?
- Do you ever worry about getting too close?
- Do you think we should be more careful about how deep we let this go?
- Have you ever been in a similar situation before? How did it turn out?
- How would you feel if I told you I was developing deeper feelings?
Communication and Transparency
- Do you think we’re open enough with each other about what we want?
- Do you feel like you can be completely honest with me?
- Are there any topics that feel off-limits between us?
- How do you think we should handle it if one of us wants something different?
- How important is it to you that we’re clear about our intentions?
- Do you think we’re being transparent enough with each other?
- How would you like us to handle misunderstandings or conflicts?
- How do you feel when we don’t talk for a while?
- What’s something you’ve wanted to say but haven’t yet?
- How honest are you with me about your feelings?
Future Expectations and Goals
- What do you see happening with us in the next few months?
- Do you think we should talk about where this is going?
- How long do you see us continuing this way?
- What would make you want to take this to the next level?
- What would you do if you wanted more and I didn’t?
- How do you see this fitting into your future plans?
- How do you think we’ll know when it’s time to either move forward or part ways?
- Do you think we’re on the same page about what we want for the future?
- Do you think we should set some expectations about the future?
- How do you see me fitting into your future plans?
Setting and Respecting Boundaries
- What do you need from me to feel respected in this relationship?
- How do you approach setting limits in a casual relationship?
- Do you feel I respect your personal and emotional boundaries?
- How do you feel about sharing personal details with each other?
- What’s your comfort level with public displays of affection?
- Is there anything you’re uncomfortable with that we should discuss?
- How often do you think we should see each other?
- Are there any emotional boundaries you’d like to set?
- What do you think about discussing our situationship with friends?
- What’s your take on staying over at each other’s places?
Exit Strategy and Closure
- How do you think we should handle it if one of us wants to end this?
- How would you feel about staying friends if this ends?
- How do you think we can avoid unnecessary drama if we decide to move on?
- Would you prefer a gradual or a clean break if we need to end things?
- How do you think we should communicate if one of us wants out?
- How would you like us to handle seeing each other socially after this ends?
- What’s the best way to avoid hurting each other if we need to end things?
- Are there conversations we should have now to prepare for a potential end?
- How do we manage expectations if we see an end approaching?
- What would make you feel like you’ve had proper closure if we ended this situationship?
