Boolean operators in ruby are short-circuiting: if it is possible to determine the value of the expression from the left-hand argument, the right-hand argument isn't evaluated.
Therefore, a simpler mental model for evaluation of a boolean expression involving && is to consider first expressions involving only two operands: the left-hand operand is evaluated first; if the value of this operand is nil or false, the operand is returned and the right-hand operand isn't evaluated; if the left-hand operand is anything else, the right-hand operator is evaluated and its value is returned.
From this definition, it's clear that, as you note, expressions involving boolean operators don't return true or false, but simply a true value or a false value. It's worth noting that this doesn't make any difference in a context where a boolean expression is used only for its true-ness or false-ness.
Hope it will help you.