Anaya usually does really well if I give her her bottle in her play pen and she puts herself to sleep. Maybe Jesse could give him a bottle in there and then just sit there with him, maybe even rubbing his back or head or whatever he likes while he is in the crib with his bottle. Also, will he fall asleep in the car? If so is it possible to transition him to bed when the car ride is over? That could be something to try to start out. I hope you find something that works.

I was nursing Ewan down for a long time and it was getting hard so we finally decided he had to go to sleep in his own crib without me nursing him down. He still wakes up in the middle of the night and joins us in the bed but that is something to be worked out later I guess. What we did to get him into the crib at night was read stories and then nurse or bottle sitting up and then I placed him in the crib and let him know mommy is right next to him. First I sat next to him on the floor and patted his back through the bars and then I laid down on a pillow and whispered to him. He was a bit upset at first and cried but I was surprised at how short his crying about it was. The first night was only about 10 minutes of crying with me there and then he just laid down and went to sleep. Then following night was less than that and the following day even less and now either his dad and I can go in and put him down with no nursing or bottle and he lays on the pillow and goes to sleep. We stay in the room and wait for him to fall asleep. Sometimes he looks up to check if we are there and then puts his head down and drifts off. It has turned into a ten minute process from being placed in the crib to drifting into a complete sleep. It took less than a week for him to accept that as his new routine.

jessica, is it possible for you to skedaddle for an hour or two a couple of nights a week while jesse puts him down?

i ask because for over six months now, while i'm at work, ari puts abigail to sleep .. no bottle and (obviously) no boobie, though she takes a few drinks of water from her sippy.

the other 5 nights a week, i do nurse her to sleep, but just knowing that it's possible for her to nod off without tears and without boobie shines a big light at the end of the co-sleeping tunnel.