First, address the clipless pedals. These can be your best friend if you master them. Answer this: if you are sitting still on your bike, one foot on the ground, the other on the pedal, which foot is most likely to be on the pedal in the ready position?

For me, it is my right foot. It is the first foot to come unclipped when I stop. Figure out which is your "unclipping" foot and practice unclipping just that foot and stopping.

Another thing to consider are your pedals. I've heard so many great things about other brands of pedals, but I stick with my Shimano SPDs for one particular reason: you can adjust how easy or hard it is to clip out. I keep it on the easy adjustment so I can get out of my pedals easier if need be. Perhaps you should check to see what pedals you are using, try out some Shimano SPDs if you're not using them already, and adjust them so they're easy to clip out. This alone may solve your problem.

Group Rides

You are never going to get up those three hills if you don't try. The sooner you start, the sooner you'll conquer them. There is absolutely no shame in walking up a hill. Everyone has done it. (If you haven't, then you need to come here and ride ).

Go to the group ride. Release your husband from any responsibility of keeping track of you and riding with you. Do your own thing.

Oh, and ask your coworker if he'd be willing organize a ride with you, him, and his female friends. That way, he can ease your shyness on the first ride and help you get to know the other gals.

Be brave. Have fun. You'll soon wonder why you didn't try this sooner.