For me there are multiple red flags, but the two big ones. 1) You state this woman finds you physically attractive, which boosts your ego. 2) You mention Condition 3 pocket carry is for peace of mind not reality.
These two aspects are part of a larger underlying issue that you need to look to resolve and involve both a mindset change and some tactics to produce said mindset change.
Mindset:
1: You need to learn how to not need to have your ego stroked by any one person. You cannot find healthy, stable, relationships, or even contentment in life if you're not able to be comfortable with yourself.
2: Comfort with yourself extends to being comfortable in your surroundings or comfortable in your ability to alter those surroundings to meet your needs. That isn't just being comfortable in your own skin, it's comfortable and confident in your own abilities.
Tactics:
1: Drop this woman and forget she exists.
2: In fact, if I were you, I'd swear off women for awhile. Focus solely on self-improvement. Learn new things, go to the gym and lift heavy weights, start rolling Brazilian Jiu Jitsu, teach yourself how to reload, shoot more competitions, dry fire more. Whatever you do don't choose booze, partying, or eating - none of those are improvements.
3: As part of 2...you need to get yourself to a series of shooting courses that continually press you to be a better shooter. Your decision to Condition 3 is a function of lack-of-confidence in handling your firearm and overconfidence in your ability. You need to confront the reality of both.
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To conclude:
I won't mince words or play nice about it your issue is ego. And if you don't make changes to confront and crush your ego, you will in the absolute best case - continue exactly as you are in your current status quo. In the worst case you'll end up over extending yourself and get yourself into a lot of trouble that could have been avoided entirely.
Ego is the enemy of progress and contentment. Ego is what causes us to be complacent, it is what causes us to covet, it is what causes us the most pain. Crush your ego and you'll start to win at life.