We have had the same sitter many many times with both kids and had a laps of about 1 1/2- 2 months maybe of no sitter. I knew she was forming some sep anxiety with friends and neighbors being around or holding her but that was getting better. Then our sitter came and we left like normal… about 2 hours prior to her bedtime (although her naps had been off that day) Turns out she cried the ENTIRE TIME! She said that she finally just fed her and just put her to bed and she passed out. So then last night we had an event and at first when she came DD was ok until after a half hr (I took my time being around and finish getting ready) then she started crying. It was SO SAD! Huge tears streaming down her face, sad pouty lip. We turned on her fav show and she calmed down in sitters arms, then she took them on a walk and all seemed ok. Once we got home sitter (who I know is awesome… she babysat all though school and is now 23… been with us for over a yr now) She started crying once they got back, sitter put her to bed early while she cared and fed DS, she didn't calm down so she went in with another bottle which she drank more and threw it all up plus her last bottle. Sitter gave her bath, she calmed down…. fed more bottle and rocked her with pandora lullabies… and she passed out on her (she stayed rocking for 30 min incase she got sick again) I just feel so bad and don't know how to ease separation. I also don't want my sitter to get stressed as she also has DS to take care of. We are also going away for 10 days without kids end of July and I am worried it is going to be so stressful for DD. My In laws are staying with them but they live 8 hrs away and don't see them often enough for DD to really know them. Do you think the 1 day prior to us leaving will be enough of an adjustment or I am now wondering if I should go and spend a week with the kids right before we leave.