I'm lucky that my relationships have always been very secure so I don't tend to feel insecure in relationships and second guess too much what the other person is feeling. There has been one BIG exception to that and my gut instinct that he didn't feel the same way as me (despite his assurances) proved correct.

However, I'm shockingly insecure at work. I know where it stems from but have basically never addressed it but plan to in the next couple of years by seeing a counsellor and confronting a few of my fears in a non-work environment first.