This study aims to determine the perceptions of Millennials about parenting style and challenges of Generation X and Millennial parents which may aid in the reassessment of how they nurture and guide children throughout life. Data collection was done through a 32-item questionnaire answered through a 5-point scale and 5-item open-ended questions administered via Google Forms which was accomplished by 61 Filipino Millennials from the Graduate School of UPLB. The four-part survey gathered their perspective on parenting styles, challenges, and generation gap, which were analyzed through descriptive and thematic analyses. Results show several challenges that Generation X and Millennial parents face, such as frequent use of gadgets and technology, lack of time for their children, imposition of discipline on children, and leniency of parents. In addition, results revealed that Generation X and Millennials’ perceived parenting style is authoritative. The commonalities in the challenges of both Generation X and Millennial parents are the emergence of technology and frequent use of gadgets, as well as the lack of time of parents for their children. Future researchers are recommended to have a bigger sample size and include parent-child dyads to determine their parenting styles accurately and thoroughly compare parenting similarities and differences between generations.