This study explores how young men experience and are affected by three distinct types of online sports betting: traditional pregame betting, live betting, and parlay betting. Drawing on in-depth interviews with fifteen male participants aged 21–25, the study investigates how different bet structures influence mental and emotional well-being, everyday activities, and decision-making behaviors. Using thematic analysis and a scale-based engagement intensity matrix, the study identifies key divergences in risk perception, impulsivity, emotional volatility, and financial behavior across betting types. While traditional pregame betting is largely associated with calculated decision-making and reduced emotional reactivity, live and parlay betting elicits stronger emotional swings, greater impulsivity, and higher perceived entertainment value. The findings suggest that different sports betting formats pose distinct behavioral risks and should not be treated uniformly in research or regulation. This work contributes to the literature on gambling psychology, digital betting environments, and youth behavioral health, and concludes with evidence-based policy recommendations aimed at mitigating harms.