I'm still a rookie. Sambuca is the best thing I've tried. It is often served flaming. Has a very strong licorice flavor.
I do NOT recommend a chocolate-ghost-pepper martini.
What I've found to be easiest to drink and order at a bar: vodka cranberry or margarita. A little boring but good staples. :)
Fuzzy Navels, Cosmopolitans, anything mixed with fruit juice is nice. I especially prefer Appletinis, they are awesome lol.
I also like a 7 and 7, which is a seagrams 7 Gin with 7up...rum and cokes, tell them to go heavy on the soda if you're skittish about the taste of Rum.
Also I definitely love love love Margaritas!
Schnapps are your friend when you're new to drinking. It's candy in a bottle.
A personal favorite is to put a shot of Buttershots (butterscotch) in with the contents of can of cream soda. If you're feeling extra adventuresome, throw in a shot of amaretto.
My favorites -
White Russian (Kahlua coffee, Vodka, and half&half). Wife's version is a Kahlua and Cream - same drink, minus the vodka.
Also love a Sidecar and classic Manhattan, but it's taken a while to get there. If you ever find yourself in a Brazilian place you much order a caipirinha - amazing. Also fantastic - a nice classic mojito.
It's all so good!
For a nice, light refreshing summer drink, order a Mojito. Rum, seltzer (or 7Up), fresh mint, sugar and fresh lime. Goes reat with BBQs, Mexican food and burgers. Also made with fruit flavors, but the basic is a great starter drink.
After dinner, I agrewe with the White Russian and/or Kahlua and Cream. Sweet and smooth for people starting. Also a simple alternative is Bailey's Irish Cream on the rocks. If you're a traveler and get near Jamaica, Sangster's Rum Cream occassionally beats Bailey's (in international competitions), but you can't get it in the states.