DD1 was 10 mo and we left at night when she was sleeping to make it easy on a 17 yo sitter. DD2 was 3 months (DD1 age 2) w/ the same sitter. Again, we usually go out at night 3-4 hrs to make it as easy as possible w/ the sitter.
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I think my oldest was about 3 months the first time we left her with a sitter (a friends step-daughter). We left our new little one with a sitter for the first time at about 8 weeks.
Other than his babysitter who watches him while I work? Probably 2 But not because I wouldn't have trusted someone, we just didn't have someone convenient nearby and my MIL or my mom would come visit whenever we needed to go out without him.
DD #1 passed away in January 2011 at 14 days old due to congenital heart disease
DD#2 lost in January 2012 at 23 weeks due to anhydramnios caused by a placental abruption
Our first au pair was when DS1 was 3 1/2, before that my mother or MIL would watch the kids when needed (they went to work with me for the most part). We haven't hired a "babysitter" yet, we've always been able to work our schedule so the au pair, or my mother/MIL can watch the kids.
Re: What age was LO with a babysitter?
DD #1 passed away in January 2011 at 14 days old due to congenital heart disease
DD#2 lost in January 2012 at 23 weeks due to anhydramnios caused by a placental abruption