I got lucky, I guess -- my dad (in his 50s) had some experience riding decent road bikes long long ago in a land far far away (BC - Before Colby, I'm the oldest of 4). We bought new road bikes, nearly identical (mine is WSD), just over a year ago. While he works outside and skis in the winter, he doesn't get a lot of regular aerobic exercise. We both went for it from day one and got clipless pedals (his are SPDs with wide platforms he could still ride on). Riding the road bike is sometimes a challenge for him and he's not a huge fan of bike wear, but I'm proud that he's willing to go all in and I like having an occasional riding partner.

A friend of mine recently bypassed this issue by buying a bike for her mom as a gift. They picked it out together, but she had recently gone through this process herself (and with her husband), so she kind of knew what she was looking for to start out with. Her mom has started riding regularly, and really likes it.

My husband's mom (50s) has an "average" bike herself, and 2 years ago when the folks from her practice (she's a GI nurse) decided to do a sprint tri, she decided to, too. She was a runner in another lifetime (even while Mr. Colby and his brother were kids), but since then the sprint tri was the thing that really re-energized her into exercising. Now she checks out bike trails and kicks my husband's dad's butt on the bike.

A guy I work with was recently diagnosed with diabetes (was pretty overweight). He started walking to reduce his blood sugar (that plus radical diet changes worked, he was able to go off his meds), but his body started adapting, and he's too heavy to run/jog. He got a bike and he loves it. It's really opened up a lot more options for exercise, and he can tour around without feeling like he's walking in circles. He did ask for advice before he bought his bike (and he listened to it), but the end result was the same -- another new rider, AND, he's lost a ton of weight.

2 years ago, I was pretty sedentary. I have a job that has me sitting on my butt, and I had been for about 5 years since college -- basically as much of a change as going from a non-sedentary lifestyle to a sedentary one. My husband and I started riding to work on cheapie mountain bikes (yes, we fell into that trap, but it's only 6 miles), and it was really a great entry-level exercise for us. The first few times were difficult, but it was nice to feel like you were doing something good. We slacked off, gained more weight, I took up running (maybe not so good a first choice), we started riding to work again, fast forward 2 or so years and I've ran, rode, and swam more miles than I'd care to count, and I've lost upwards of 80+lbs. It is possible to enjoy a mediocre bike, but I consider it a gateway drug.

For my husband, the bike has a low cost of entry. He can get on it, go as far as he wants, and turn around and come home. I love to ride with him, but I'm not so sure he loves to ride with me. I've got him on a 2-3 days a week riding to work (12 mile) plan, and he's willing to consider more. He has a flat-bar road bike (road components and fast tires, just flat-bar). Once or twice he's jogged with me, but it has a very high cost of entry (and that whole "you've ran a marathon" thing works against me).

Good luck, RM. If anyone can teach her to love it, it's you.