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DD has been in a twin bed since the end of August. I was very nervous for the transition, but it went pretty smoth. The first couple of nights we had to keep putting her back in bed when she'd come out of her room, and the same thing happened with naptime. Now, when we say it's night-night time she gets herself into bed, we tuck her in and that is it.
We have had a few setbacks, and I think it's related to having DS here since it just started. She'll get up really early in the morning, I'm talking 4-5AM! She comes into our room when she is up. Thankfully I can get her to go back to bed. And, naps have been much harder to put her down for this week. I'm hoping that once DH goes back to work and we're back on our schedule she'll nap better.
Can he open his bedroom door? If not I'd just shut his door to keep him in. I think the bed is one of those things you just have to go for, and not look back. It may be really hard or it may be easy. Just be consistant with putting him back in bed when he gets out and hopefully he'll get it.
DS has been in a toddler bed the past couple of weeks for two reasons. 1) he was climbing out of his crib. 2) he seemed to want to sleep in it. He would crawl into our bed and say "ni-ni" and act as though he was going to bed laying under our covers.
It was a very easy transition at night for us. We are still having trouble at nap time.