Breastfeeding With Sleeve in Pregnancy with Weight Loss Surgery Posted June 25, 2020 Hi! I got sleeved over 2 years ago and continued breastfeeding easily. I expressed milk while in Mexico and waited (I think) about 1-2 weeks until I finished one of my meds, can't remember exactly. I started back up after that and it was fine! I wouldn't have done it if my son was under a year old, I waited until he was about a year and half and it worked fine for me.