Situationship or naturally progressing toward a relationship?
I (F, late 20s) have been seeing a guy (M, around the same age) for a little over two months. We’ve met up around 20 times so far, so we see each other pretty frequently despite both having busy schedules.
We’ve been on a mix of actual dates and more casual hangouts, and most of our dates last 5+ hours.
Some context**:**
1. Neither of us has explicitly talked about exclusivity, but as far as I know, neither of us is seeing anyone else. He knows I’m not on any dating apps. We actually met in person—he approached me at a store and asked for my number. Based on what I know about his personality, I’d honestly be surprised if he were actively dating multiple people.
2. We both got out of long-term relationships relatively recently, about 2–3 months before we started seeing each other. Mine was a 3-year relationship, and his was about 1.5 years.
3. On our 7th date, we had a really meaningful conversation about why our previous relationships ended, what we learned from them, and what we value in relationships. I didn’t ask what he was looking for at the time because I assumed it might have been a bit early, especially since we had both recently gotten out of long-term relationships.
4. He remembers little things I mention. For example, I casually mentioned my favorite drink/snacks once, and on our next date, he surprised me by bringing them for me.
5. We didn’t have sex until our 7th date. Earlier on, when things got heated, he told me he could tell I wasn’t ready, that he respected my boundaries, and that he was happy to wait.
6. He plans almost all of our dates and usually picks the restaurants or activities. One time, he surprised me with tickets to a Broadway show that I really like but had never seen. He picked really good seats even though he didn’t know much about the show. He said he just wanted to make me happy.
7. During these two months, he invited me to one of his best friend’s parties. He also told me that he had told his friends about me and how we met. At the party, his friends all seemed cool and just came to talk to us.
8. He has also agreed to come to my upcoming party, where he’ll be meeting some of my friends.
However, we still haven’t had the “what are we?” conversation, and neither of us has explicitly brought up exclusivity. He can also be quite indecisive and seems to prefer taking his time when making decisions.
I’m not asking whether you think he’s secretly in love with me based on these details 😂. I’m more curious about how you would classify this situation.
Does this sound more like a situationship that’s comfortable staying undefined, or does it sound like something that could naturally be progressing toward a relationship?
And at what point would you recommend having the “what are we?” conversation? Should I be the one to initiate it? I’ve heard of the “three-month rule,” and I’ve also seen people say it’s better to let the man initiate the conversation, so I’m curious about other people’s experiences and perspectives
Posted Sep 1, 2026, 4:38 PM UTC