Girls like guys that are fun. It's a fact. Even ugly men with bad breath and pimples can get second dates, if they're funny. And being a "fun guy" isn't hard, for most fellows it just takes the right frame of mind and some stimulating activity inside the proper surroundings.
Consider the horse races; those big buildings under the bright lights at the edge of town could be fun, and they're definitely a place where ANYONE can be funny. That place is more than just local scenery - it's an exciting part of our cultural heritage, and a great sporting arena. It's a place where date designers can create lasting memories.
Here's my recipe for romance at the racetrack:
Single guys with no imagination seldom conceive of taking their dates to the racetrack, and that's the number one reason why it's such a fresh idea. Horse racing venues are massive and therefore not crowded with other single people judging you, or your lady (or worse, trying to meet her). Nobody cares what you look like here, which is also liberating. But don't go unprepared, for it's still possible to look like an absolute fool.
Relax with a Racing Program:
Buy two programs, and use one. Rest your arm on the back of her chair as you work through each race, narrating each struggle - here's your chance to be fun. Take one of those little pencils and highlight the digits as you go along. The text becomes a record of the evening's adventure so be sure and write your bets and mark which horse won etc.
The racetrack program is a storybook. It's your job to present this logbook of data as an exciting diary in which all the details of all the characters (the horses and their drivers) are chronicled. Here's how:
Don't Skip The Opening Blurbs:
Most racetrack publications begin with a journal, or a race synopsis. An expert overview briefing of this kind often highlights the races and sometimes explains the common denominators as well as the small differences between the horses in each match. Use this information to invent a funny story, and then reinforce your drama with details found deeper in the documents.
Learn How to Read a Horse Race program:
This article cannot help you decipher the nomenclature of the spreadsheet, but you can learn that valuable skill anywhere. Here's a handy download (.pdf) available at Standardbred Canada.

Proper use of the racing program is pivotal to understanding the horse races, and therein lies the prime component needed to craft good stories. Let me explain:
When your companion settles her beautiful mind on a particular horse, you should be able to relate that animal's age, weight and colors, how many races it has run, and how many of those it has won, or placed 2nd or shown 3rd. Veterans can relate pole position details, medications, and handicapping information like weights, blinders and weather preferences. The driver or jockey is also part of the equation, and also has stats to be scrutinized. And so the elements of story can be inserted anywhere; for example I like to imagine that some of the riders are involved in a love triangle, or a power struggle inside the stables. Each contestant is desperate to win this race, for all the wrong reasons. Invariably my date will root for the female jockey to win the race and outshine both of her imaginary male suitors, and so a story is crafted and will play out with a natural gravity that makes the whole event personal and more compelling; each race is a giant inside joke.
How To Bet on Horse Races:
Racetrack betting is a big part of the fun, and probably the largest cultural proponent of the entire experience. Win, place and show bets are pretty straightforward, but exactors, triactors and superfectas can get a little confusing. Take time to learn the combinations on this simple harness race betting game before you go to the race track.

Let's pause here to remember that your sole objective is to win her respect, and make her cherish spending time with you. So of course you don't actually care about the races and therefore it's sensible to keep the bets small and just have fun. If possible, get a table outside where you can see the horses coming, and hear the thunder as they pass.
Trip to the Paddock:
Women love horses. Human females have an inherent bond with this part of the animal kingdom and most girls experience a latent desire for a pony at a very early age. The female passion for all things equestrian surpasses their love for all other animals. Most women will even admit to having childhood notions of themselves as Princesses riding horses and loving Princes who are also on horseback. And so any romantic trip to the racetrack must connect you and her with horses - you do that at the paddock.
When touring a paddock, don't be afraid to engage other spectators in productive conversations about the horses. That's what this building is all about. Once again try to form a personal connection between yourselves and the names and numbers on your racing program. Once again you'll find that creating a story here involving a horse that's right in front of you now, will pay dividends at the race's conclusion in fifteen minutes time.
Find the Track Photographer:
Watch the crowd of people that saunters out onto the gravel surface of the racetrack at the conclusion of the race. It's usually the winning horse's owner, and his or her family and their friends. Here's something not many people know - track photographers work for themselves. They sell those rigidly posed Winner's Circle photos and candid action shots to the owners for money, and that's how they make a living. In conclusion, most will shoot anything for money, including you and girl.
When the next race ends, watch the track photographer do his business and approach him afterwards when he's least occupied - while he or she is waiting for the next race. This entrepreneur will oblige your photographic needs for a reasonable price, but don't settle for a posed picture in front of the grandstand. Leverage this professional's access to restricted areas and get shots with the winning horses at track level or in the winner's circle. This is not uncommon - put $50 in his hand and he'll take you to the roof! This is how you really cement good memories into that special girl's consciousness. As long as that huge color photo sits on her dresser mirror there can be no forgetting the wonderful time you spent together at the horse races.