Introduction: A substantial percentage of patients undergoing bariatric surgery are of childbearing age. Pregnancy outcomes after bariatric surgery are known. However, there are limited data on the impact of pregnancy on weight loss after surgery. Objectives: This study aims to evaluate the effects of pregnancy on post-bariatric surgery weight loss trajectories (WLTs) and to determine the association with age and initial weight. Methods: All who had primary bariatric surgeries (Roux-en-Y gastric bypass or sleeve) between September 2015 and July 2020 were classified into two groups: post-surgery gravid (GG) and post-surgery non-gravid (NG). WLTs were examined using a random intercept mixed-effects model with repeated measures nested within patients. The post-surgery/pre-gravid time phase (PoPG) was modelled using a third-degree polynomial. For GG, two third-degree spline functions modelled the post-surgery while gravid (PoWG) and post-partum (PoPP) time phases. Age and initial weight were used to control for pre-existing differences during PoPG. Weight differences at 6 months PoPP were examined by applying general linear hypothesis testing to the mixed-model results. Results: A total of 508 patients were included, 20 in GG and 488 in NG. The mean age at surgery was 33 years in GG and 37 years in NG. The mean initial BMI was 47 kg/m2 and 43 kg/m2, respectively. During PoPG, adjusted average weight in both groups follows the path across time. For GG, weight decreases and then increases during PoWG. For GG during PoPP, weight immediately decreases after delivery and then increases over time to levels similar to NG. Weight differences at 6 months PoPP for GG and NG were not statistically different. Older age was associated with reduced weight loss during PoPG by Baseline Age, while higher initial weight was associated with increased weight loss during PoPG by Baseline Weight. In both instances, these effects attenuate over time. Conclusions: This model indicates that pregnancy following bariatric surgery affects WLT during PoWG and PoPP, and no difference in weight is expected after 6 months post-gravid. Age and initial weight could be considered prognostic factors during PoPG. Patients wishing to conceive should undergo preconception counselling and be advised to avoid pregnancy during the period of rapid weight loss. They also should be informed that WLT may vary during pregnancy and early post-partum.