That is what he would typically drink, because he did find that it made the taste more tolerable (plus he felt that it was even more masculine than just whiskey and ice). As someone who really enjoys a good Old Fashioned, I find it deeply tragic that he would force himself to drink something he merely found "tolerable".

It's very silly. Some of the masculine people I know are guys who are secure in their own masculinity. They drink whatever beverages they like, they paint their nails or wear eyeliner if it would suit their outfit, they wear a tutu and have a tea party with a young child — in short, they integrate masculinity into who they are in a healthy manner, rather than living their life subordinate to some abstract, impossible ideal.