I am not a fan or "crying it out", either. Your child probably feels like you are leaving him at night, so the goal is to make him feel secure and to have a positive attitude about sleep.
A consistant routine is the key. For example, our routine is dinner, bath, teeth, books, stories, & pray.
After we talk about our day, we pray. After prayer, I say, "Good night, Daniel. I love you. Whould you like pancakes or cereal in the morning?" He makes his choice.
Then, I DO NOT TALK TO HIM. I have a little chair by his bed in which I sit and hold his hand. I take this time to pray for my children and for my family and to thank God for all my blessings. It is a precious time and I would not trade it for anything.
My son just turned 4 now and it is during this peaceful time before bed that he shares the most with me. He is a VERY active boy (and if it wasn't for this peaceful quite story/prayer time I would think the kid had no sensitive, compassionate thoughts).
Just the other night he started telling me after we prayed, "Mommy, you can go to your bed now." I respected his privacy and left the room. I went to my room and cried, cried, cried. Why? becasue my little boy was growing up!! Your 3 1/2 yr old my respond to a routine like this. He may not share much for a while, but you can tell him sories about his day until he gets comfortable abd will do it himself.
All the best! Liz