I still say go for it!
I’ve read your post about the guy who broke your leg and how you didn’t tell the police he did so and when I read this post after that one, I think you have a tendency to not step up to the plate — whether it’s doing the right thing for others or yourself.
Low self esteem is at the bottom of this problem, so focus on that and continue to push out of what you think your comfort zone is and do the right thing every time. One day you may have a daughter and you’ll want her to do the right thing for others as well as for herself. Start practicing to be the person worthy of that daughter, today.
This guy sounds great; he’s single; so are you. You have a real connection — you can balance your career and a relationship. Go, go, go!!