I was hoping to talk in person last night but he surprised me with something and I didn't want to kill the mood. Then earlier this morning he wanted to postpone plans we had for tonight and I told him I wanted to talk to him about something. He called me at lunch and told me whatever it was we should talk now, and I gave in, but wasn't really prepared as I was planning to do it later.

I told him I didn't want him to feel like he was a bad person for helping out someone who was depressed, but that I had been thinking about the text exchange and wanted to know what he meant by him replying "I miss you." He said it meant nothing. I told him that he was leaving it open for interpretation after she said she'd been dreaming about him, and he said he thought it was the polite thing to do and asked me how I would have handled the situation. I said "I would have changed topics because that would make me uncomfortable" and he agreed that he wouldn't necessarily like it if I had done the same thing as him, but would understand if I explained the situation. He said that the worst case scenario was that she may have been feeling sad and alone and was reaching out in a "are you still there/do you still have my back" kind of way and thought that the safest response was to reciprocate. I asked him again what he missed about her and he said "nothing that's just what you respond when someone says I miss you. You say it back."

He also said that he didn't think that her saying she's been dreaming about you meant anything, and I disagreed, but then he screenshotted the image and sent it to me and what she actually said was "You've been in my dreams lately" and so I guess I could see how he would interpret that as her just looking for an excuse to say hi instead of trying to say she's still into him.

At the end of the day, he defended what he said, said that it's probably going to happen again in a few months, and that while he would try his best to keep things unquestionably platonic, he didn't want to feel guilty about it and then got mad at me for nagging him. To be fair, I have been bringing up petty things lately, and that doesn't help that earlier this morning I was a bit annoyed (and told him I was annoyed, but also let him know it wasn't his fault) that our specific plans for tonight were getting postponed for literally the 5th time, and he got mad that I was annoyed.

The conversation ended with him being upset that I have been stressing him out lately "with little things like this" and I told him that while I hate stressing him out and try to communicate in a way that doesn't offend him, I'm not sure it's fair to expect me to not be disappointed about situations from time to time and that I'd like him to be someone I can come to. He ended up ending the conversation being mad at me.

I'm definitely seeing him either later tonight or tomorrow and I'm not sure what I think of his explanation. He did admit that it wasn't the coolest thing in the world for him to say that, would do his best not to leave room for interpretation open, and assured me it meant nothing and also told me he really doesn't think she's trying to get with him, but he also got mad at me for bringing it up and nagging him.

I'll let you guys know on what I decide but if we're going to break up I'd like it to be when everyone is feeling ok and not emotionally charged.

EDIT 9/28: I just wanted to say I had a break up talk with him but will post a (hopefully short) update once the dust has settled and once I feel I can provide helpful insight that can be applied to other situations.