Finally got my boyfriend on board!

Ask if he set a goal for himself for the week. Not a weight loss goal, but a goal like "eat veggies at least 3 times this week" or "exercise at least 2 hours this week" or whatever. If he says no, just share a mini-goal you set for yourself and maybe ask him to support you in reaching it. From then on, just share your own mini-goal each week and ask for his support. He will probably come up with some mini-goals of his own and share them, so just support him whenever he does. Just make sure you're not trying to make your goals his goals too.

The above isn't necessarily what you need to do exactly, just kind of describing the concept of how you can get a guy to open up on his own by just sharing about yourself. That's the style that works on me since pushy or demanding would just cause me to pack my bags. It plays on my desire to be the man making the decisions, and it also lets me appreciate how important the girl was in helping me reach that decision. If your guy isn't like that, don't take my advice

So I guess my question is this:
How can I continue to support him as he starts this with me? I want him to have what he wants, but I don't want to be naggy. Do I just leave him be and let him ask me questions when they come up? Or do I make small suggestions about our everyday lives?

Realize that just because YOU are on a diet and need to eat low cal, low fat etc foods, he will do the same. Realize that he might bring in "bad for you" foods (which really aren't but thats a different debate) and it is ok for you to either have some or explain to him before hand that a no from you once should be the end of him offering (bonus points if you can explain it to him in a loving way).

The very MAIN thing for him to do in the start is to try and be within his calorie range. He can do it any way he wants. Eating KFC, ice cream, cheetos, veggies, lean meats. ANY WAY HE WANTS. As long as he is under the calories set by MFP. That is the start that will take him further than anything else. He will obviously feel fuller by eating more veggies and "healthier" foods compared to cheetos and ice cream but many people get off the track with too much dietary restrictions. So suggest to him to keep about 20% of his calories for naughty foods and the rest for healthy more nutritious foods.

Try to keep the menu interesting. Both of you. Don't be boring with your foods. You can have LOTS of foods that are high in flavor and low in calories. Explore other cultural cuisines. They can often be cheap on the pockets too. Try out lentils and beans. They're a protein and nutrition factory. Combine with veggies and spices you have complete and nutritious meals for like 500 calories tops. Theres lots of other foods like these!

My boyfriend also finally got on board with getting healthier!

I have been encouraging him by doing the following:

1. If it looks like he is losing weight, mention it! Congratulate him, and ask how much he has lost. Talk about any new muscle definition you notice.

2. I've been cooking healthy breakfasts and dinner for my BF. Egg white omelettes with spinach (I can trick him into eating a cup of spinach with breakfast!) For dinners, I have been making him chicken breasts with different vegetables.

3. Any time I go for a snack of fruits or vegetables, I offer to get him some from the kitchen too. He usually says no, but he has been saying yes more and more often.