For the last few months we've mostly been no contact but I checked up on him a few times and wished him a happy holiday and happy birthday. I used more endearing terms lately too see how he would react and noticed a subtle positive response from him, and a few compliments which he hadn't given me since we broke up.
A few days ago he messaged me asking me how I was, which is the first time he took the initiative to check on me, and he seemed kind of affectionate at first but then started to reply a little late then hours late (to be fair I replied a little late from the start as well because I was busy)
I basically told him some of the problems I was having were solved, he said he was happy for me and I left it at that. What should I think of it? Do you think I should try to break no contact further?
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To be honest, I'd take this as a sign to keep your distance from your ex for now. He says nice things to you occasionally but doesn't really follow through. From your description it doesn't seem like he's putting in consistent effort.
I know you still care about him, but don't set yourself up to keep hoping he'll change when his actions aren't matching his words. Responding hours late is a pretty strong signal he's not that interested in really reconnecting.
If he steps up and starts initiating more quality conversations with you on a regular basis, maybe you could think about easing up on no contact then. But until that happens, I would just stay friendly rather than pushing things further.
Don't get hung up on crumbs of attention from him, you deserve someone who treats you like a priority! Focus on yourself and people who really wanna be in your life. He knows how to find you if he wants to.
I know it's not easy sis, but staying strong on no contact is best for your healing right now. You've got this! Let me know if you need an ear.
I think you are not very smart for trying to get back with your ex. What's next? Trying to make him jealous? Have some dignity and self respect and move on. It's over.