I struggle initiating Intimacy

I’m a 31 year old male, and I’ve had several “physical” relationships. I’ve never had a relationship where initiating intimacy was an issue, it always seemed my partners would usually start and we would go from there. I like having a meaningful, committed relationship. I’ve had the one I’m in now for about 6 months now and she is very shy when it comes to initiating intimacy, the problem is so am I. If we are ever to do anything I’m the one that has to start it. Every. Time. I find it awkward and daunting. We’ve had multiple conversations about it and it always ends with the “we both should try harder” trope but there’s no improvement on either side. I know what I want here but I can’t ever find myself to pull the trigger, then when we part ways I’m always kicking myself… Why? Why is it so hard for me? I just dont get it… I want this thing to last but I need to get my head straight here, what should I do?