Dear Caitlin: I just scored a date with a cute girl a few cubicles over. I know she likes bourbon, and I like to drink whiskey, but I don’t know much about either one. I want to seem knowledgeable, but don’t want to spend a ton of money.  Help?—Greg, Washington, D.C.

This is Ask a Bartender’s favorite kind of question: the intersection of romance and drinks. It’s easy to buy a pour of Michters 23-year at $75 a shot and look like a baller. But in my opinion, it’s way more awesome to be able to find something value-oriented on that first date, something you can reasonably find, purchase and drink again on the third date when you bring her back to your place for a nightcap. Here are a few tips to help you get to that point!

  1. Head out on the right night. You’ll get the best service and have bartenders most amenable and eager to give you some recommendations if you head out on a Tuesday or Wednesday evening. Avoid Monday: that’s industry night, when most of your experienced bartenders are on your side of the bar, and a lot of good spots are closed. If you’re going out Friday or Saturday, pay lots of attention to tip #4 below and be ready and willing to yell to be heard over the cacophony of the unwashed weekend amateur masses.
  1.  Choose your location accordingly. Do some research and find a bar with a good selection of American whiskeys—but one that isn’t too high-end. Cross-reference whiskey bars with dive bars, and where the two meet, you’re going to find some killer deals on some really great whiskeys. They often have amazing bottles at a per-shot price that’s significantly lower than the fancier, newer bars. They might also be more likely to have those hard-to-find small batch whiskeys than the places where wealthy people will go. Important: Check out the bar before your date so you’re comfortable bringing a new cutie there.
  1. Do some recon. When you’re flirting at work, ask your date what her favorite brands are while taking mental notes.  Upon returning to your cubicle, Google whatever it is she said. Find some common descriptors amongst the various brands at a site like whiskey.underthelabel.com, and commit them to memory. What’s a descriptor? Check out the taste-related adjectives of the bourbons she likes and identify similar words for each label.
  1.  Be straight with your bartender. Let the barkeep know what you’re looking for—American whiskey, preferably bourbon, price point from I’m-not-cheap to I-can-still-pay-rent, spicy overproof rye/brown sugar and clove/floral and delicate, etc.—and ask him or her to suggest a few options.
  1.  If all else fails… Does she like caramel/brown sugar/round whiskeys? Go with some Kentucky Old Bardstown—he black label is cheap as hell and seriously delicious. Your bold lady wants something boozy, but still easy-drinking? I’m a huge fan of the Old Weller Antique 107 Proof. Is she into floral, delicate whiskeys? The Four Roses yellow label is a gorgeous, inexpensive pour.  Is it her birthday? You should probably spring for some Old Forester Birthday Bourbon. It’s not super expensive, but not super cheap, and hey—it’s her birthday!

The best thing about being two folks out learning about new whiskeys is that you can assemble a flight of several options and taste them side-by-side to discover—together—what you like and don’t like. This builds conversation into the date, and you’ll create a shared experience that you can reference for future outings. Just remember—use this info to be confident in your interactions, don’t second-guess yourself, and you’ll have a great time. Cheers!

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