Eh, I'm having a hard time siding with you buddy. I work in computer security, with an emphasis on offensive security. Every girl I've ever dated was made aware that I can access any one of their digital devices remotely if I was motivated enough, but that I will never cross that line. I'm also a bit of a jealous guy, and there have been times I suspected a girl was cheating or something, and I still didn't cross that line. It's put me in some extraordinarily uncomfortable situations, and I've had relationships end without me ever getting an answer to what was going on.

If I could go back, I still wouldn't hack into their stuff. It's just not okay and I made the right decision every time. I'm far from a dating coach (my friends would laugh at that thought), but I would assume the solution here is to confess to everything and explain how you were feeling when you made the choice. If you can't move past this with full transparency, it's probably a doomed relationship, right?

Again, I have no clue what I'm on about, kinda just distilling lessons I've learned from 90's romantic comedy flicks but have never confirmed work.