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Ok, so we have been crating at night....with the intention of eventually letting the dogs sleep elsewhere. I want to find out what other people do with more than one. I would like to have Fenway sleep in my room, behind a closed door and let Shiloh sleep with my daughter or in the living room or basically wherever he wanted outside of my room. My concern is whether or not Shiloh will feel slighted to not be with Fenway....are we better off keeping them together or is separation of the boys an ok thing to do? I don't want to damage their self esteem, lol

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Our guys sleep where ever they want to. Mariner usually sleeps near Sharon, even if she falls asleep on the couch. Boomer will sleep on the landing of the steps and Shayna will sometimes sleep near Boomer or on the couch. Besides crating them I don't know that you really can control where they sleep.
Sorry for the multiple post - don't know what happened
You will NOT damage their self esteem whatever you decide.
I would say once you are confident they will do okay out of crates, I'd say try out your preferred scenario and see how it goes.

All ours sleep in our room on the floor in their dog beds--Rosco always sleeps by my side of the bed and the rest sleep against one wall or along the foot of the bed. Thule and Cass switch spots but we make sure Rosco gets his same spot or else he'll bark for it later in the middle of the night.

Having them sleep in our room works out best because if they are anywhere else in the house they will go on alert.
Our dogs sleep wherever they want. Ned is weaning off the crate so he still often is put in it for night - by me. If we have children (young adults) around, they will steal one of the older two dogs = they each have their favorites. They then close their doors to keep the dogs with them (or the dog will sneak back to our room after the kid falls asleep). Our dogs sleep on our bed, in a doggie bed, on the landing or sneak onto the living room couch (a no no). They kind of have their favorite spots but it isn't set in stone. None of them seems to be sad or feel slighted with any of this. They love it when a kid "steals" them but seem very happy with us too. I think if you don't worry about it, it will naturally evolve, and I think if you set up a habit, that will be great also.
Ours sleep where they want, they both sleep in our room. They go to sleep together and between 10 and 11 every night Molly gets up and goes into the crate. Abby sleeps on her bed or on the bottom of ours....

Abby is 16 months old now and we kept her in the crate until she was one. She wanted to play at 6:30 in the morning. Molly is 10 months old, likes her crate and sleeps until 8:00

Try the sleeping arraignment you would like when you are comfortable with them out of their crates...
Willy sleeps in our family room. His crate is open and he is free to sleep wherever he wants in that room. On the sofas or the cold stone of the fireplace. (Usually his favorite spot as he's a hotty) He's often in the crate when I come down in the morning. LiLi sleeps in our room in her own bed. Eventually we will bring Willy up to our room, but we tried it once and they wanted to play in the middle of the night. They make a lot of noise when they play, so . . . maybe after he's older. He's only 5 months now.
Thanks for all the replies. We have tried letting them sleep together without crating....and they just play. So for us it is crates or separate rooms. Both options work, they are good in their crates and they are good in separate rooms. Fenway prefers to be in the room with me, Shiloh doesn't seem to care where he sleeps.
Fergie has always slept with us on the floor when she was a baby and as she got older she'd come up in bed for only about 5 minutes - she gets hot. Now I've got the puppy and Lucy as to be in a crate over night as she would pee someplace for sure. I'm still working on getting Lucy to sleep through the night. Last night I let Lucy out of the crate but in the back hall which is big enough for Fergie too. Since Fergie's in heat she can't be in our room. I was surprised but I put her in the back hall with Lucy and they both did sleep until 5 this morning. No accidents from Lucy either. Fergie will sleep anyplace but in a kennel. She hates a kennel. Lucy doesn't mind too much though. It's all trial and error when they are puppies
We crated our first doodle until he was about 11 months old, then began leaving the crate door open and he chose to sleep at the bottom of the stairs (he's not allowed upstairs!!), and occasionally on the couch (he's not supposed to do that either!!). When we got the new puppy, now 18 weeks old, we began using the crate for him. But, he would wake up really really early and bark for hours until we got up, he also kept peeing in the crate (we were taking him out half-way through the night as well). Eventually, after a lot of lost sleep on our part we decided to let him sleep out in the living room. Since then, apart from a potty break, he has slept through the night until we get up. The funny thing is, the other morning my husband went downstairs and couldn't see our older dog - he had curled himself up as small as he could in the puppies bed that we had left in the crate!! (Even funnier as our older dog usually hates the crate!!)
Lucy sleeps on our bed so I know where she is at night. Fergie sleeps wherever she wants. Usually the door is open and she sleeps in the sunroom which is tiled. I think she like it 'cause it's cool. Lucy won't have "an accident" on our bed so it's good that she's up there. Up until now she hasn't been able to jump down. Hopefully, she'll be house trained through the night before she figures out how to jump down.

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