This study aimed to describe and analyze the spokesmen's politeness strategies and gender bias in their utterances when making a marriage proposal in Manggarai, Indonesia. This study was under the philosophy of interpretivism with the employment of descriptive qualitative design. Six spokesmen in three different marriage proposals were the main source of data. Since the researchers were participant observers, relevant data notes were taken. To support the observation data, the researchers conducted interviews and documentation studies. Dwelling pragmatic theory, the obtained data were analyzed through some stages: data reduction, data display, and drawing a conclusion. It is discovered that on record without redressive consisting of positive and negative type is predominantly used as a strategy followed by redressive and off the record. In addition, gender bias was found in the use of the figurative language of metaphor, simile, and symbolism in the spokesmen’s utterances. In order to have effective and meaningful interpersonal relationships and communication, it is, therefore, crucial that we understand what to say and how to say it.