Truthfully, I don't love dairy but I've tried doing it for the calcium. Some things I tried/Comments:
1. I did try the WW smoothies. I did the chocolate flavor. If made with water it is one serving, with milk it is 2. On the plus side, it didn't taste bad and it is a simple way to get in dairy with calcium. However, for me, it caused bloating. Like many people I've become more lactose intolerant over time and I have a real problem with drinking milk. If it didn't cause the bloating though I would just do the smoothies.
2. If you like yogurt, use it. DH makes oatmeal with fat free plain yogurt and adds fresh berries every morning. Or, my son has made smoothies using the fat free plain yogurt and fruit. Personally, I find yogurt horrible tasting so I don't do any of that. But, if you can tolerate yogurt it is a great choice.
3. Cheese, preferably lowfat or nonfat. 1 1/2 oz of cheese is a serving. I like the WW string cheese, jalapeno flavor (I had trouble finding it and finally found it at Walmart). It isn't a full serving but it is a good snack and only 1 point per piece. Also, I use reduced fat cheese on sandwiches or reduced fat shredded cheese in salads. This is where I get most of my dairy.
All of the above said, I don't personally think that dairy itself is all that necessary. I think it is calcium in the diet that is important and that can be gotten from other foods or through calcium enriched products (such as calcium fortified orange juice or almond or soy milk that has calcium added to it).