Hi we did one for the first time last year and it was a huge success. We ordered heart shaped lollipops that came with a to/from card. We ordered them from Cedar Creek Fundraising http://cedarcreekfundraising.com/lollipopstore.htm
and shipping on them is free. We used the ones called Dear Hearts. Here is basically what our flyer said:
"Send a Candy Gram to someone you love! Parents and family members can send them to the children and the kids can send them to friends and teachers! A candy Gram is a packaged Gourmet heart shaped lollipop with a To/From card attached. Each lollipop costs $1 and you can order as many as you like.
The Candy Grams will be addressed to the children and delivered to them in their classrooms on Valentines Day (Tuesday, February 14 th).
We have a sizeable amount of lollipops, but they will be sold on a first come, first serve basis, so get your orders in early. We do sell out."
At the bottom of the flyer was a form for them to fill out child's name/class and then we gave them 5 slots to list the to/from information and noted if they needed more then 5 to just attach a piece of paper noting the to/from information.
We have two women that do all the addressing. We ordered the lollipops in advance and they addressed them as the orders came in. We sold over 900 lollipops so that is a lot of addressing.
We ran the sale for about 10 days and ended the purchasing on the Friday before Valentines day so that the women had the weekend to finish up the addressing.
Lastly, we did have the teachers keep track of which kids got lollipops ordered for them as the orders came in. We did not want any child not getting a lollipop. We gave one signed from a special friend to any child who did not get one. We actually ran about 15 short on lollipops for this but the teachers and principal who got so many lollipops from the kids handed over some of theirs so that no child had to go without. We ordered 4 cases (960 lollipops) and we have about 370 kids in our school. It was the perfect amount as we had nothing left over.
Also the parents were very receptive to this as it only cost them a dollar to buy their kid a lollipop. We got lots of compliments and a few parents who told us to come up with more $1 fundraisers. We made over $800 with this and it was so simple. It certainly is not a windfall but it was a nice little extra way to earn some extra cash. Good Luck!