Dating and Starting Relationships • aidenjackson • 23d ago

What’s the best way for me (34F) to navigate my 'situationship' with him (36M)?

I'm embarrassed to be asking this at my age, but I really care about this guy and don’t want to ruin things. So, there's this man I've been seeing—let's call him John, because I think that name suits a privileged guy pretty well! We met at work when he was covering our location for a couple of months. I found him attractive, but since we were colleagues, I tried to keep things professional. Fast forward four months after we stopped working together—I ran into him at a work event, and we were both being flirty. He insisted that I join him and some others at a bar afterward. I had prior plans, so I told him I would stop by if they were still out when I was free. When I got off work at 10:30 PM, I texted John to see if they were still out, and he said, “Yes!” and told me to come to his place. I figured no one else would be there, but I went anyway. One thing led to another, and we ended up sleeping together that night. Since then, we've been in this complicated dating/friendship situation. A couple of months back, he let me know he’s not ready for anything serious or exclusive since he just got out of a long-term relationship and doesn’t want to hurt me. However, I felt hurt that he waited until we were already so close to tell me this, especially after he pushed for us to sleep together. Here’s where it gets complicated: I’m head over heels for this guy, and he has no idea how I’m feeling. At one point, I reached out to see if I was misreading signals since he hadn't been asking to hang out. He reassured me that I’m one of his favorite people but reiterated that he’s not ready for a relationship right now. I recently messaged him to say that I’d like to discuss our situation the next time we meet. To be clear, I would love to have a relationship with him, but I’m worried about approaching the topic the wrong way. Should I wait longer, since it's only been about 3.5 months? Should I lay all my feelings out on the table? Or do I just need to be more patient? The thought of him possibly seeing other people really bothers me. HELP!


infernohawk19 • 23d ago
It sounds like you're in a tough spot! What is your main concern about discussing your feelings with him: the fear of rejection, the possibility of ruining your current connection, or something else?
evathunderwolf • 23d ago
It’s tough, I get it! Be honest about your feelings when you meet. Share your concerns, but also listen to him. Clear communication is key, even if it feels scary. You’ve got this! 💖
penelopespecter • 23d ago
Navigating this situation can be tough, but honesty is key! It’s great you’re considering a conversation. Share your feelings openly but without pressure; you deserve clarity. If he’s not ready, respect that; it shows maturity on both sides. Trust your instincts, and remember, relationships evolve at their own pace! Good luck!