I am concerned for you. You are asking for life advice from strangers on a website who have few qualifications to advise. However I am tempted to give some. The plot is thickening, i.e. you have shared that you may be losing both romantic and professional chances due to your perceived lack of aggressiveness.
You are a man like every other man in your group. You have as much ability as others, and apparently more integrity than many. Moreover you are appealing to your female friend as you have noticed. But you have not acted on this lead. Do not sell yourself short. You may be struggling with the same problem we all face in the world: how to forge ahead against competition while maintaining personal integrity.
The first step is faith in yourself. You have earned your current position by your ability and potential. What is the next step? I am reminded of a self help book I used to read that explored the fears we all have that hold us back. The one that resonated with me was the fear to stand up for oneself. Once you leave home, no one will stand up for you unless you do so yourself.
If you do not want to be side tracked in your job and your relationships, I encourage you to decide what you want, and then to ask for it. This is like a situation I encountered when my department Head declined to let me teach my specialty course, giving it instead to someone who did not have my expertise.
One Friday I made up my mind to make my case. After meditating on it over the weekend, I met the Head in the coffee room early Monday morning and made the argument that I was the local expert in the subject and I wanted the chance to teach the course. He gave it to me.
It is similar with women. Ask them to go out with you. And do your homework, plan a nice evening at a nice restaurant, or concert. Give me a break, if other guys can entertain a girl, you can too. At any rate you can learn to. Like everything else it takes practice, so give yourself some.
This is not a one way street, i.e. you also have something to offer. When you realize that you would not even have a job unless your company thinks you are worth more to them than they are paying you, you begin to understand the possibility of bargaining.
I used to think I was a microscopic particle and so lucky to have a job. Then i realized there was a reason they gave me the job instead of someone else. I asked for some percs and i got them. ... Give yourself a little more credit. Others will too.