Why is he happy if I see someone else if he likes me?

[Anonymous]

Long story short, I met this guy through work but because of our circumstances we couldn’t be together. Both left our jobs about a month ago and moved on with our own lives but I always found his communication was shit. I didn’t want to get upset without confronting him first but during that I said maybe it’s best if we stop talking and he kept saying he still wants to message and that he won’t forget about me and how he can’t speak to me like how he speaks to other people but then he kept saying how he understands why I feel the way I do and that his intentions were never to hurt me. And then I told him how I have a date and he seemed really happy like he kept saying ‘Sounds really cute!’ ‘Hope it goes well for you! Xx” etc.

Surely that’s a sign he doesn’t like me? Because why would he be happy to stop talking and be happy for me to see someone else if he liked me? Or am I being stupid?

[HollyK21]

Okay, let’s try to dissect this.

“Both left our jobs about a month ago and moved on with our own lives but I always found his communication was shit.”

Unless you’d like to clarify, you stated here that you always found his communication was bad. So for you to then say: “I didn’t want to get upset without confronting him first”, if this is pertaining to his lack of communication, then I don’t understand why be upset when you already knew his style?

“but during that I said maybe it’s best if we stop talking”

I’m really hoping you were clear with him here and didn’t just suggest stop talking. It’s very indirect, and he’d have no idea of your reason why.

“he kept saying he still wants to message and that he won’t forget about me. But then he kept saying how he understands why I feel the way I do and that his intentions were never to hurt me.”

I gutted that a bit to save space, but to me this statement is all the clarity you need. This was basically a flirty office dynamic on his end with no real intent behind it. That is why he’s happy for you moving on and he’s repeatedly wishing you well. I’m sure that is hurtful because you were under another impression, plus it seemed like working together was the only obstacle and now it’s not. At the end of the day though, what matters is what’s happening in present time and he isn’t trying to get serious.