One of the secrets to keeping your WW points or calories down while still being able to keep your family happy without cooking two meals is to limit your serving size of the higher point entrees and supplement with lots of no or low point side dishes (one of my favorites is a variety of roasted veggies). Both the stuffed peppers and enchiladas below could totally blow your allowances for the day if you don't exercise moderation, but you can still enjoy them in small portions.
Stuffed Peppers - 7 points (serving size, 1 stuffed pepper). This is a favorite with Rachael's family, and can be made in a slow cooker and is freezer friendly. I like her suggestion to freeze in individual serving sizes to make it easy to grab just one serving. Serve with some roasted veggies or fruit or green salad to help fill you up. Add ons for family could be bread, rice or potatoes, and/or dessert.
Balsamic Pork Tenderloin - 3 points (5 oz. meat per serving). This is a great entree that allows for a generous serving of meat without any guilt. Rachael blogged about it awhile back, and talked about how great it was with a new baby in the house. The recipe called for it to be made in a slow cooker, but she used her Instant Pot. It could also be completely prepared ahead of time and then frozen - a perfect gift for someone who is recovering from illness or surgery, or who has a new baby. With the low points (the new point system is lower than in Rachael's blog post), you have the freedom to add a number of side dishes. An easy one would be roasted veggies that add no points, salad with lite dressing (2 points), fruit salad or indulge in one of the family add-ons. Add ons could be potato salad, crusty bread, cole slaw, and/or dessert.
Sour Cream Chicken Enchiladas - 9 points (use lite sour cream, medium sized tortilla, and 1 enchilada per serving). This recipe is a favorite with my oldest daughter's family. This is quick and easy and a great way to use up leftover chicken. To round out the meal, add a salad or other fruit or veggie side dish. Add ons for family could be refried beans, tortilla chips, and/or dessert.
Spicy Seafood Combo - 3 points (serving size is 1/4 recipe). This would make a great company or date night meal when you are looking for something extra special. Serve over 1/2 cup rice or quinoa (3 points) and add a salad with lite dressing (2 points). Add ons for family could be bread and/or dessert.
Vegetarian Taco Salad - 7 points (serving size is 1/4 recipe without tortilla chips. Skip the oil in the dressing and use feta cheese.) I have found that a lot of recipes that call for oil in the dressing don't need the oil at all. Add 6 tortilla chips to your serving for an additional 2 points. Add ons for family could be tortilla chips and/or dessert.
Tomato Cheddar Soup - 5 points (serving size is 1/6 recipe without croutons. Decrease cheese to 1 1/2 cups, and use extra sharp cheddar, and decrease oil to 1 tablespoon.) Serve with a slice of crusty bread (2 points) spread with 1 tsp. butter (2 points). Add ons for family could be the croutons in the recipe, garlic bread, extra cheese and/or dessert.