First dates are an enigma within themselves. Many times, the two participants know very little about the other person - including likes and dislikes, personality type (i.e., expressive, analytical, driver, amiable, or a combo), religious and political beliefs, and overall outlook on life.

And while the unknown can seem daunting and unpredictable, a first date has the potential to be an enlightening and exciting experience. In fact, the less you know about the person you’re stepping out with, the greater the opportunity to ask open-ended questions to gather information and get to your date and what makes him/her tick.

So here are four first-date ideas – along with the ideal beverages to go with them – that are all designed to take the awkwardness and unpredictability out of the experience.

1. Hit the Kentucky Bourbon Trail

Ninety-five percent of the world’s bourbon is aged and bottled in the Bluegrass State. Taking a tour of the Kentucky Bourbon Trail will allow you to experience the bourbon-making process, learn about the recipes and the history of each facility, and to take part in a good after-tour tasting session.

Transportation is provided to and from the distilleries for obvious reasons. There are 13 distilleries available to tour, but we recommend that you sign up for a one-day tour, visiting three at the most.

Almost nothing warms up the soul like sampling the country’s finest bourbon. When you’re evaluating which bourbon to sample, focus on the ones that have been aged at least ten years.

While almost all varieties will taste smooth as you are swallowing, the real test is in the next five seconds afterward.

Some of the bourbons aged for five years or less tend to cause what some call a “bounce-back” effect, leaving you with a harsh aftertaste and a distorted facial expression that may not be ideal on a first date.

Also, don’t forget to purchase a bottle or two or your favorite bourbon before leaving the distillery. You won’t look like a cheapskate, and you can hopefully both enjoy these warm tasting memories on future dates!

2. Enjoy a Minor League Baseball Game

While taking in a major-league baseball game can be a pleasant experience, nothing quite matches the spontaneous, fun-loving atmosphere, and absolute craziness that a minor-league baseball contest can provide to a couple of the first date.

And despite being surrounded by the good-natured madness, there is a downright cozy feel to the minor league experience.

Fans at a minor league-baseball games witness the most bizarre and wacky events, such as oversized mascots racing each other around the base paths on tricycles, children on the field leap-frogging one another to win a T-shirt, a contorted-face contest on the large jumbo screen, and many other silly events.

Minor-league baseball is a spectacle within itself, and it’s conducive to a relaxed, laid-back atmosphere in which most fans don’t even know or care which team eventually won the game.

Most minor league parks will offer a wide variety of beverages to enhance your experience. While most fans will opt for draft beer in plastic cups, we recommend getting a large bag of peanuts at the start of the game and complementing it with a mini-bottle of chardonnay that’s available at one of the concession areas.

If you’re absolutely a red wine fan, you can certainly go in that direction as well, but don’t underestimate the surprisingly tasty peanut/Chardonnay combo.

And while your overall number of salty peanuts diminishes inning-by-inning, you may even need an additional bottle of chardonnay to quench your thirst.

But please try not to overdo it – it’s better for the bases to be loaded instead of you!

3. Take a Trip to a Local Microbrewery

With craft beer sales making up almost 22% of all beer sold in the U.S., the microbreweries are making a significant impact, and they’re here to stay.

If you reside somewhere in America, the chances are excellent that a microbrewery is within easy driving distance.

If you begin early in the afternoon, you may be able to experience three or more microbreweries in your area before the night is through.

Be sure to keep Uber or a taxi service on the contact list of your cell phone, just in case.

Microbreweries are fun places to take a first date because of their laid-back atmosphere. In many facilities, you can bring along snack foods to enjoy, while some customers play board and trivia games as well.

You can usually choose among a myriad of brews that are produced right in your neck of the woods, and you can enjoy them at a table or booth right in the same location.

Usually, your choices will be vast, and you can decide among light and dark beers, ales and lagers.

Many of the options have different alcoholic content, which you will need to keep an eye on since some of the local brews can contain alcohol up to and over 10%.

Whether you have one type of beer that you are loyal to, or you enjoy a variety of brews, make sure you are open to new tasting experiences when you visit a microbrewery.

It’s always fun to purchase one beer with a lighter texture and another with a darker texture at each site you visit.

It’s a good idea to ask for a couple of extra glasses so that you can share each other’s choices and compare and contrast the two types.

The experience will loosen the both of you up and encourage more spontaneous dialogue. At the end of your evening, you can grab a meal at a nice restaurant to put an exclamation point on the entire experience.

4. Visit a Bookstore


Almost everyone loves spending time in a bookstore. It’s a magical place with rows and rows of books, each one calling your name, each offering you the ability to escape into a completely different world where you can be entertained, educated, and enlightened.

The bookstore offers a truly unique experience, and it has untapped potential as an ideal place for a first date.

The combined smell of new books and fresh coffee brewing from the café create an almost surreal experience.

It’s a great place to find common ground with your date. Order a latte or cappuccino from the café – and share a cookie as well – when you first arrive.

Ask your date which subjects might interest them. Do they enjoy reading as much as you do and, if so, which genres do they prefer? What books have they read recently, or which ones do they remember reading as a child?

Ask the right questions, and you will find out more about your date than you ever thought possible.

Agree from the start that you will not leave the bookstore until you have both purchased a book. Help each other find the ideal book and you’ll find the fun behind this exercise was in the journey itself.

You can play little games with each other during the process of trying to guess the number of pages in a book that you’ve randomly pulled off the shelf.

When you’ve each chosen your book, spend a little time in the bookstore reading the first few pages.

Then, compare notes and try to make a second date within a couple of weeks to discuss your book and what you liked or disliked about it. And who knows where the second cup of coffee and your miniature book club could lead?

Your first-date experience may lead to short-term or long-term romance or, then again, it may not. But no matter which way it turns out, use this time to get to know the other person, allow them to get to know you, and try to relax and enjoy the present moment.

And here are a few last-minute words of advice to help make this experience even more perfect:

  • Talk less about yourself and more about your date. Everyone loves a good listener, and you already know plenty about yourself.

  • Imbibe responsibly. A slight buzz is fine, but remember that no one wants to babysit someone who is intoxicated. And since we’re talking about it, keep the number of a taxi service or other transportation company ready in case you need it.

  • Put past relationship behind you, at least for one evening. The first-date experience is an opportunity for a new beginning and bringing up ghosts from your past will not enhance the experience of your date at all.

  • Stay in the present. Don’t try to predict the future or to over analyze where this relationship may or may not be going. Life, from start to finish, is a series of experiences. Treat your date with respect and courtesy, and you will end up having a very good time, whether it’s just a one-date stint or the start of a long relationship.

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