FTM random questions

sphynx920

DH and I have been wondering about some things for a few days now and I thought to ask the experts: other moms. So I ask you all...

1. When is a good time frame for LO not to wear a hat all day/night?

2. Same thing, but for mittens? I hate seeing him with scratches on his face...

3. Are we spoiling DS by picking him up whenever he cries? He seems to want something every time, but I feel like everyone tells us to "let him cry". I feel horrible doing that, especially since he wants something (hungry, diaper change, etc.) 

Thanks in advance!