Instead of assigning names to a group of people to purchase specific gifts for specific people during the holiday season, have everyone purchase a gift with a price limit. During your holiday party, everyone receives a secret Santa gift from someone in the group.
Plan a theme around the types of gifts for everyone to purchase. You can use a holiday spirit-inspired theme and require everyone to bring any gift that contains snowflakes or starts with the letter H (for holiday). This should produce a wide range of gifts, from mittens to scented candles to homemade cookies. If you want to keep the gifts under tighter control, make your theme more specific. For instance, ask for cooking utensils, cold weather gear like nifty handwarmers or scarves, homemade recipes with the recipe attached or office-related items like stationery and snazzy pens. Then, request everyone to purchase an item for the grab bag that is related to the selected theme.
Instead of having the group draw numbers to decide the order, plan to hand out the gifts as the host. You may even want to get in the holiday spirit and wear a big fuzzy scarf or a shiny top hat. This idea works well if you have a group of school-age children, as they will love watching you walk around looking goofy, as you are handing out gifts. When each child arrives with their wrapped present, have he or she put his or her name on a small tag and attach it to the gift. Then, set all of the presents into a large bag or box. The name tag will ensure that you do not hand a child the same gift he or she brought for the grab bag and your handing out of the gifts will allow everyone to open and enjoy their present at the same time.
If your grab-bag party involves a large mix of both men and women, do a gender-neutral grab bag. Be sure to set strict rules with the gifts, including a price limit, a list of appropriate items, like homemade cookies, empty picture frames or a gift card to a local restaurant. If there is an odd number of people, purchase an additional gift or two to add to the mix so everyone will have something to take from the grab bag. Be sure to request each guest to remember what his or her gift looked like before he or she places it in the grab bag. Then, draw numbers to decide who goes first.
If you will be celebrating with a group who all get together a few times a month to enjoy the same activity, like a book club, use that as your starting point. Ask each member of the book club to purchase his or her favorite book to add to the grab bag. Everyone should bring a book that hasn't previously been read during your book club meetings (hand out a list beforehand of all of the books that have been discussed at the book club to each member). During the grab bag "meeting," draw names of authors to see who goes first, using the first letter of the last name to see who goes first.