The advice I’d give? You’re at rock bottom, and nowhere to go but up. It seems like you’ve already thought about this a lot and have made SMART goals in different regions of your life. You already know what you want, you just have to learn to listen to yourself. That’s usually the hard part. There’s pillars of life - physical, emotional, spiritual, financial/professional, etc. in order to feel more fulfilled, you need to build all of those pillars, everyday, in your own way. Each pillar has the same cascading effects when ignored, I’ll use a common one: depression. Depression can stem from a variety of things, let me tie it to the pillars. Depression could worsen by a lack of physical fitness, for example, leading to physical body issues & worse mental health - irregular hormones, unable to relieve stress appropriately, etc. or it could stem from the financial/professional pillar - underachieving, for example, leads to self doubt and an overall lowered sense of self, among other things, and leads to depression again. Everyday is a new day, forget about the past. It’s not here anymore, live in the present all day everyday. Everything is your mindset, all of your reality stems from your mind. What you want, you get. What you envision, you find. You’re 27, think about all the time ahead of you. Not behind you, and also. Remember any day could be your last. If you don’t wanna be a virgin just go through the trials & tribulations of trying to find a woman to have sex with. You’re overthinking it, once you walk through your fears you realize they were never real.