Hi Stace, I have a 2 year old boy too. He never had separation anxiety for the longest time, then he developed it all of a sudden just after he turned 2. He cries his little eyes out and holds on really tight to me whenever I leave him with someone other than daddy and it breaks my heart too! What I've learned though is that he cries for literally, 30 seconds after I walk out the door and is just fine afterwards. Our routine whenever we leave him is this: Maybe the 10 minutes before we go, we tell him that we are leaving and who is coming to stay with him and how much fun they'll have, which he'll usually be excited about. Then, when the babysitter arrives or when we take him to where he'll be staying, we tell him how much we love him (that's mostly for my own peace of mind that I've told him that!) and hug him and kiss him. Then we leave promtly, crying or not, without going back to try to calm him down. I'll usually call whoever is with him a little later to see how he is and, without fail, he's always been just fine and happy. It's like pulling off a band-aid, you gotta do it quick! It is important to keep leaving him and to always say goodbye, not sneak out. I have friends who have had toruble with their little ones because if they had snuck out, the kiddo is never assured that they are coming back and it could create trust issues. It's just a phase and he'll grow out of it. In the meantime, we get to teach him how to be independant and to trust you! Good luck to you