120 Conversation Starters for Situationships

Let’s not pretend situationships aren’t confusing. You’re vibing, you’re talking, maybe even spending a lot of time together—but no one’s calling it anything. And sure, you could just go with the flow, but also… what are we even doing?

If you’ve ever wished you had better things to say than “wyd” or “lol that’s wild,” you’re in the right place. These conversation starters are built for where you’re at—no pressure, no cringe, just casual ways to connect, flirt, or figure things out (without sending a 2 a.m. paragraph).

Lighthearted Icebreakers

1. What’s something totally random that made you laugh today?
2. If you could eat only one meal forever, what would it be?
3. What’s the weirdest thing you believed as a kid?
4. Have you ever had a completely useless talent?
5. What’s your go-to way to waste time when you’re bored?
6. Which app do you open first when you wake up?
7. If your life had a background soundtrack, what genre would it be?
8. Ever had a super strange dream that stuck with you?
9. What’s your current comfort show or movie?
10. What would your walk-up song be if life had intros like baseball games?
11. If you could instantly master one skill, what would you pick?
12. What’s the funniest thing that’s ever happened to you on a date?
13. What’s one thing you never leave the house without (besides your phone)?
14. If pets could talk, what do you think yours would say about you?
15. What’s your idea of a “perfectly lazy day”?

Flirty and Playful Starters

1. So… do you always smile like that when you talk to someone you like?
2. What’s your idea of a subtle flirt? Asking for a friend.
3. Be honest—did you already stalk my socials before we started chatting?
4. What’s one thing that usually gets your attention when you’re into someone?
5. Are you more of a slow-burn type or instant spark kind of person?
6. What’s something you’ve wanted to say to me but haven’t yet?
7. What’s your flirting style: words, looks, or actions?
8. What type of compliment do you actually like hearing?
9. Would you rather text all day or meet up in person?
10. What’s the most attractive trait someone can have, in your opinion?
11. What’s something subtle that turns you on?
12. What’s your “I like you” behavior?
13. Ever caught feelings when you weren’t supposed to?
14. What kind of texts do you secretly look forward to getting?
15. If I dared you to plan a fun night for us, what would it include?

Shared Interests, Hobbies, and Passions

1. What’s something you could talk about for hours without getting bored?
2. If you had a free weekend, what would you love to spend it doing?
3. What’s your current obsession—TV show, game, hobby, anything?
4. Is there something you’ve always wanted to try but haven’t yet?
5. What kind of music just gets you?
6. Are you more into chill nights or spontaneous adventures?
7. What’s your go-to comfort activity when you need a reset?
8. Have you ever picked up a random hobby just for fun?
9. Do you prefer doing creative things or more physical stuff?
10. If we had a day to just vibe, what would we do?
11. What kind of places make you feel most relaxed?
12. Any bucket list activities you secretly want to cross off?
13. What do you do when you just want to feel inspired again?
14. Are you into learning new things together or keeping hobbies separate?
15. What’s something you’d totally invite me to do with you someday?

Questions to Learn About Each Other’s Lifestyle

1. What does a typical day look like for you?
2. Are you more of a night owl or a morning person?
3. Do you usually make plans or go with the flow?
4. How do you usually spend your weekends?
5. What’s your ideal way to recharge after a long day?
6. Do you like being around people or prefer alone time?
7. Are you someone who sticks to routines or likes switching things up?
8. How often do you like socializing versus staying in?
9. What’s something small that makes your day better?
10. How do you feel about spontaneous plans?
11. Is your space more cozy and lived-in or minimal and tidy?
12. What’s your relationship with your phone like—always on or barely touched?
13. How do you handle stress—ignore it, vent it out, or distract yourself?
14. How often do you like catching up with someone you’re seeing?
15. Do you believe in “me time” even when you’re seeing someone?

Conversations About Feelings

1. Do you ever get mixed signals in this kind of situation?
2. How do you usually deal with uncertainty in dating?
3. Is it easy or hard for you to talk about how you’re feeling?
4. How do you usually show someone you care—without saying it directly?
5. Do you think people can have feelings without wanting commitment?
6. How do you figure out if you’re catching real feelings or just in the moment?
7. When things feel unclear, do you bring it up or just go with it?
8. What’s your personal way of checking in with yourself emotionally?
9. Can you usually tell when someone is into you emotionally?
10. What do you think matters more: time together or consistency?
11. When you start liking someone, do you keep it to yourself or drop hints?
12. How do you feel when things start to shift emotionally in a situationship?
13. Do you ever worry about getting too attached?
14. What’s your take on emotional boundaries—are they helpful or hard to set?
15. What’s one unspoken thing you wish you could ask in a situationship?

“What Are We?” Questions

1. Do you ever think about where this is heading?
2. Are you okay with things being undefined right now?
3. Have you had a situationship before—how did it go?
4. Is this something you’re seeing as casual or maybe more?
5. How do you usually know when it’s time to define things?
6. Do you believe every connection needs a label?
7. Would it feel weird to talk about expectations or no?
8. What are you hoping this will or won’t turn into?
9. How do you feel about exclusivity in a situationship?
10. Do you feel like we’re on the same page right now?
11. What would “too soon” look like for you in terms of talking about labels?
12. Is there anything you’re unsure about with us?
13. Do you want something light or are you open to more if it happens naturally?
14. What kind of clarity do you need in something like this?
15. If things changed between us, would you rather talk about it or let it be?

Fun Hypotheticals and “What If” Scenarios

1. What if we woke up tomorrow and swapped lives for a day—what would surprise me most?
2. If you could teleport us anywhere right now for a chill date, where would we go?
3. What if we had to pretend to be a couple for a week—how do you think we’d do?
4. If you could fast-forward this situationship six months, what would you want to see?
5. What if we were the leads in a rom-com—what’s the title?
6. If we had a shared playlist, what’s one song that has to be on it?
7. What if we had to go off the grid together for a weekend—what’s your plan?
8. If we were stuck in an elevator, what would we end up talking about?
9. What if we couldn’t use phones to talk for a week—how would we stay in touch?
10. If we had a time machine, what’s one moment you’d want to redo or relive?
11. What if you could read my mind for one hour—would you take the chance?
12. If this situationship had a theme color, what would it be?
13. What if we planned a “just because” date with zero rules—what would we do?
14. If you had to describe us as a vibe or aesthetic, what would it be?
15. What if one day we looked back at this—what do you think we’d say?

Boundaries in the Situationship

1. What makes you feel most respected in a connection like this?
2. Is there anything that feels off-limits for you right now?
3. How do you like to handle space when things feel overwhelming?
4. Is it okay if we check in now and then about where we’re at?
5. What’s one personal boundary you really value?
6. Are you more into frequent contact or space between hangouts?
7. What’s something that might feel too serious too soon for you?
8. How do you usually deal with emotional burnout in dating?
9. What’s one way someone can show they’re being mindful of your limits?
10. Is honesty something you’d rather hear gently or directly?
11. Do you prefer slow and steady or going with the moment?
12. How much emotional availability do you have right now, honestly?
13. Are there any situations you’d rather avoid for now?
14. What kind of pace feels good to you in something like this?
15. Do you think it’s okay to ask for clarity without pushing for commitment?

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Final Thoughts

Situationships aren’t always easy to handle. They’re full of maybes, mixed signals, and moments where you’re not sure if you’re doing too much or not enough. But talking—genuinely talking—can help you feel a bit more grounded, even if the whole thing feels undefined.

These questions won’t solve everything, but they can help you connect, understand each other better, or even figure out what you really want. You deserve to feel heard, seen, and sure—whatever this is.

And hey, if you’re asking all the right questions but still feeling unsure… maybe it’s worth asking yourself something too: Is this really where I want to be? Or do I deserve something a little more certain?