In my experience these feelings ebb and flow depending on the situation. As an example feeling jealousy (not pathological!). If you're meh about a guy, you're going to get off easy if they meet their "one". If it was someone you deeply cared for it hurts a lot more.
The same with all behaviours and emotions. We move in and out of them all the time. Sometimes maturely, at others less so. I would love to never ever feel insecure again but it's a remote chance I'll escape that feeling, with or without a partner. Not sure why I'm waffling here. Oh I know it was a comment about hoping to overcome something by facing it.
On a good day I can feel yes I don't feel that way, but a week later maybe I do and I realise nope I didn't overcome it! Excuse the brain dump.