When I was riding to the center of town, to train myself to ride to work, it was a bit demoralizing at first. I had been ill for years so I had to walk up hills and rest a couple a times on the way( 15 miles), plus have a couple hours break between riding back.
The ride home was harder, as it is uphill, always has a headwind and there are always two or three huge fit men that just zoom by, made me feel like I am going backward.
All I wanted was to go on the big rides, that I would see zooming by me , like the Tour!
Now I can do twice a week! Plus a ride on weekends, alt weeks.
you can always call a cab if you dont have anyone to pick you up!
My riding buddy said, if you ride to to work a couple times a week, that should train you up for big rides. So increase your rides during the week, as you get able.
I havent made one yet( as I have to ride 20 km to GET to the group rides, then they are 22 to 55 km, plus ride home) but I am working on it.
I read women dont push themselves as much as men exercising. I recently said ok, and kept up with some really fit people for 5 km or so, which was a first.
I do interval training, to learn how to keep pace.
Conquering illness, one step at time.