Background Generally, recurrent teenage pregnancies are public health menaces that impede the quality of life of teenage mothers, their offspring, and society as a whole. However, there is paucity of information regarding factors influencing this social issue especially, in developing countries where Ghana is no exception. Moreover, this menace has been least investigated from the perspective of the teenager with multiple pregnancies. Hence, this study aimed at identifying the factors influencing recurrent teenage pregnancies and the challenges confronted by these teenage mothers. Method This study is a phenomenological qualitative study that was conducted in the Effutu Municipality in the Central Region of Ghana. Employing convenience and snowball sampling, 40 participants who were residents of the study area, had a child each, and were pregnant at the time of the study were included. Other participants included teenage mothers who had at least two (2) children. A face-to-face in-depth interview with the help of an interview guide was conducted. Proceedings were recorded, transcribed, and analysed using thematic analysis. Quotations were used in the result presentation. Results The results of the study revealed that factors influencing recurrent teenage pregnancies are multifactorial. It includes peer pressure, parental neglect, poverty, living with a partner, and inadequate knowledge of family planning. The teenager with recurrent pregnancy is confronted with financial difficulties and is faced with stigmatisation in the society where she finds herself. Conclusion To this effect, it is important to intensify education on family planning and good parental practices among parents with teenage mothers while providing a similar form of sensitization for members of the society about the harmful effects of stigmatisation on the teenage mother and her children. Again, a social support network for teenagers with recurrent pregnancies could be formed to help curb this public health menace.