Hey, really good write up.
A couple of salient thoughts about your post, some of these could apply to more than the newbies.
Very few people spend time practising the basic stuff - the brake is the most powerful force on the bike (you can decelerate faster than you can accelerate 99% of the time). Learning to be progressive with the brake and how much brake is important for the road - reading the road surfaces and conditions, and developing the ESP required for riding also takes time. I've been on two wheels pretty much all my life, and I've crashed too - I reckon mountain biking is the ultimate way to upskill - it's relatively low speed, and the skills are transferable. Or a motox bike, although more damage/speed.
I've crashed enough to know that you can wipe your own butt with one hand. Just shuffle a little to get the position right. Breaking ribs is worse, especially lower ones - bowel movements really hurt. And compound fractures are cool since you get big scars.
So, the girlfriend. This is the tough bit - you need to balance your freedom to do stuff that puts you at risk, with the fears and concerns of your life partner. It's tough to get this right. Good communication is key. The other thing, if you have a really trusted mate who could 2up your partner - do a ride to mission bay in the summer. Something really slow and gentle, and get her to understand that it's a good vibe. There really is no easy answer for this. It's a time and confidence thing for her.
The reality is that we ride and we are at risk. Make sure that your affairs are in order, (get a will), and get life insurance - this is a basic responsibility to the people you care about.
I'd also suggest that you take an advanced riding course, there's lots around, and spend time on a deserted carpark practising progressive braking...
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