The question that this article seeks to answer is if the age and cultural background of a male youth interferes with the effectiveness of formal mentorship. The study from which this article is drawn employed a quasi - experimental design with a control group in determining the effectiveness of adult male participation in formal mentorship on male youth self-esteem and connectedness.  The study participants were 52 mentees and 13 adult male mentors. They were drawn from Kiserian town in Kajiado North and Kajiado West constituencies of Kajiado County, Kenya. The mentees were out of school male youth aged between 15 and 23 years, from different cultural backgrounds in Kenya who live in Kiserian Township. Post-test results showed that mentees’ self-esteem improved by 7.89 points (from 16.81 to 24.70).  The study though, confirmed that the divergent mentees’ post-test self-esteem means were not significantly different across age categories at F(2, 23) = 1.311, p =.289. The ANOVA analysis results however indicated that cultural background had an impact on the effectiveness of mentorship on self-esteem; F (7, 18) = 2.675, p=0.044. The paper therefore concludes that though a mentee’s age may not significantly impact on the effectiveness of mentorship on self-esteem, the cultural background can/may. Recommendations are made for mentorship be made available for all male youth but studies be conducted to find out what aspects of the different cultural background make this intercept on self-esteem possible.