Mine go outside as soon as the last frost date is over. They get morning sun/afternoon shade. During the winter they stay in the greenhouse at above-freezing temps.

My guess would be that yours just isn't getting enough light....

i think wildflower is right. bright light or some morning sun is best and keep them on the dry side.
here is a pic of one that a friend has. she has the best luck with them of anyone i know. during summer, they get sun until about noon and shade thereafter and bloom every winter. pretty, huh?
this one is very large and i would guess rootbound in a 6" clay pot. she never feeds it.

Wow, Jeff! I have not seen a Jade Plant bloom that profusely before. What does she use for fertilizer? I have a very old one that I keep outdoors until just before frost. It has bloomed, but not like the one in your pictures.

My Jade plant does well in a window with a lot of light although it does dry out quickly. It does not bloom like the photo shown. I would love to know what it takes to get those beautiful blooms!!

I had a huge jade plant that I had for about 8 years and I decided to try and get it to bloom last year so I left it out later than normal and of course forgot about it one night and well it's history now. Luckily they root so well from cuttings that I have another I had started from it. It is the easiest plant for me. They need very little water. My mother-in-law always waters hers too much and it is very scraggly. I had mine outside all summer last year on a covered porch in partial sun and seldom watered it and it loved it. Greenhouse for the winter would be great, but I would keep it outside as long as you can keep it from getting too wet in these rainy periods.

i am going to guess about what she does to make it flower.
first, it is an old plant with a "trunk" that is about 2" in diameter. it is definitely rootbound so that may be a factor. she does not water often, maybe once a week, and it gets quite dry in the clay pot.
i don't believe she fertilizes at all but, if so, maybe once during the growing season with a time-release.
it stays outside on the porch from spring until the threat of frost. then, it goes into the dining room with no direct sunlight. i think it may be much like a christmas cactus in that it responds to the cooler temps(from leaving outside during late autumn) and shorter length of days when it flowers.