When Ben was born, my brother gave us his old crib. Luke had always seemed okay in his little bed and I liked the idea of him not being able to get out of bed whenever he wanted. But then in the last few months he got enough will power to climb out. Plus, it got so that he just looked too big for the bed. He always seemed curled up in the corner and I finally decided it was time for him to graduate to a big boy bed. Luckily, my brother gave us one of those too :)
I wasn't sure how Luke would react since he doesn't love new things and hadn't complained about his current sleeping situation. But we took him to the store and showed him the bedding we picked out for him. When I showed him the picture of the bed on the packaging and told him it was Luke's new bed, he got this really shy, excited grin on his face.
We set up the bed the next night. Luke was out of his mind excited. He jumped on the bed and wouldn't get off it. At night time, we put him in bed and he just settled right in like he'd been doing it all his life. He seemed really pleased with the whole thing. If he is wound up or not totally tired when we put him down, he will get out of bed and play in the room. But he has never tried to leave the room once we put him down. So all in all, it's been a fairly easy transition.
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