@MadPhaseBat You need to keep pushing yourself and keep practice escalating, it will get easier over time. You need to have the attitude of not giving a fuck about the outcome. Could it be you are afraid of rejection and being open with yourself, so you're holding back?
You should just be thinking about having fun and it doesn't matter what the outcome is, you just need to go for it. You're a man, you're meant to lead when it comes to escalating.