I am what I call a situational drinker. I find certain cocktails are best enjoyed in certain environments, so I always drink in accordance with the mood and place.
  1. Manhattan
    Share one with someone special when you're snuggled up in the coziest booth of an old school bar.
  2. Kir Royale
    Buzzy and flavorful; best enjoyed when celebrating something. The Kir Royale I had at Tower Bar after getting engaged was the best drink I've ever had.
  3. Negroni
    The perfect cocktail. Enjoy outside with some olives in the early evening.
  4. Old-Fashioned
    Classic; drink one at lunch with colleagues and pretend you're Don Draper.
  5. Mint Julep
    Go for the Julep during the spring or summer, at a sporting event or a decadent brunch. Gingham should be involved whenever possible.
  6. Pimm's Cup
    In the springtime, walking in a garden, wearing pastels. Bonus points if you're in the English countryside.
  7. Piña Colada
    Equal parts sweet and satisfying. Drink alone, by a pool, with nothing to do but read a book or heaping stack of magazines.
  8. Corona with Lime
    Best enjoyed on a beach during the hottest part of the summer. Wear your bathing suit.
  9. Red Wine
    Red wine should be had while cooking (and subsequently eating) Italian food with a big group of people you love. Or with one particular person that you love.
  10. Rosé
    Tastes like summer. Pair with a baguette and cheese on a picnic blanket. Split the bottle with your bestie and drink from plastic cups. Or straight from the bottle because you forgot the cups.
  11. Mulled Wine
    Comforting and seasonal; make your own (your kitchen will smell amazing) in the fall or winter and sit near a fire under a big blanket.
  12. Margarita
    The Margarita is most perfect when had at a loud Mexican restaurant with 3 or 4 friends + a massive bowl of chips and guacamole. Don't be ashamed to order frozen with a salted rim.
  13. Bloody Mary
    Pair it with your biggest sunglasses at a recovery brunch with a non-judgmental friend. Extra spicy, save the celery for last.
  14. Boozy Punch
    Enjoy this communal experience at a classic (and slightly cheesy) restaurant with a huge group of college friends. If I had my pick - a Scorpion Bowl at The Kong in Harvard Square.
  15. Gin & Tonic
    Mix up a G&T when a raucous dinner party is ending and games are beginning. @carolinek's legendary Christmas party certainly comes to mind.
  16. Vesper
    Highly boozy but utterly delightful; order it at a hotel bar alone and strike up a conversation with the bartender or other travelers. Fun Fact: I love this drink (and James Bond) so much that Vesper is my cat's name.
  17. Mai Tai, Zombie, Singapore Sling
    For that one night a year when greasy Americanized Chinese must be dined in, not taken out - go all the way.
    Suggested by @BWF