Guy friend asking a "hypothetical what if" about dating?

I have a boyfriend and love him lots. But my brother and my boyfriend pointed out that I've been calling my guy friend Simon too often. Which I suppose makes sense, so I've been reflecting on it. Simon and I have known each other for 6 years. He regularly video calls me around midnight or later (which I'm OK with since I have insomnia). We just study, sometimes chat, usually silent over call.

Guy friend asking a hypothetical what if about dating?

As you see in the text, he admits he was flirting. And then later, denies that he ever flirted with me...

Guy friend asking a hypothetical what if about dating?

Somewhere along the way, he dropped a "you're attractive, you have your own personality". But I assume it wasn't genuine, since he seemed to be comforting me when I mentioned feeling insecure.

Guy friend asking a hypothetical what if about dating?

After some more talking, I told him I had to go. It was late, I had to sleep. Then he threw such a curveball question at me. It shocked me a lot. I don't understand why he would ask that. I know Simon mentioned this other girl and how he watches himself around her.

Overall, it was worrying because I crashed over at their apartment (a bunch of old classmates). Despite never talking to Simon or me gossiping about our past, my girl friend Anna made a side comment about him. After a few days of partying and sleeping, Anna said "I hope you don't mind me asking but... Simon seems to care about you a lot. He kept turning back to ask about you. Is there history?"

I guess... Simon decided to deny flirting (even though he said he did) because he remembered I've been with my boyfriend for a few years. But I'm not really sure what to do for the friendship besides pretending nothing's wrong? Overall I just hope this was a fun story and read for someone on this forum haha

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* side note: when I mentioned the flirting, it was a few years back before I started dating my boyfriend. Simon doesn't flirt anymore. But that's why I mentioned that my friend noticed he seems to still care about me a lot.

I did tell Simon that we need more boundaries and to keep it PC between us.
Guy friend asking a "hypothetical what if" about dating?
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