After consulting with my bartender friend, we came up with these observations.

The most manly drink you could order is straight whiskey / bourbon / scotch. That's about as John Wayne as you can get.

Martinis...just to clarify. With gin martinis, never shake them because it destroys the flavor. Vodka martinis by default are shaken very hard to get ice crystals on top.

Pina Coladas...not a guy's drink. Unless you're in the Bahamas on the beach, but on the rocks only. Then, when in Rome...but not as bad as ordering a Daiquiri.

Red Bull...neutral by itself, but what you mix with it makes the difference. Vodka and Red Bull may be acceptable if you're tired and need some pep. But mixed with just about anything else, it becomes feminine. Red-headed sluts (jager and cranberry) are usually feminine drinks, but guys can drink them with girls who are having one.

As far as Jack & Coke is concerned...when's the last time you saw a girl order this? This is my drink of choice. Always a guy drink, with any whiskey (like Crown and Coke.) Rum & Coke is more neutral.

Mojitos...a Cuban / machismo drink. If Ernest Hemingway can drink one, don't you think any other guy can drink one? But some girls may like this as well.

Just since so many people asked, whiskey sours are okay for guys (no cherry).

Margaritas, on the rocks for the guys. No frozen drinks for guys.

Of course, if you're going for the "may be gay" angle with the girls, order anything you please.

ScottieK