Day at the Track Proposal

If the outcome of your marriage proposal is a sure bet, then you should look into doing your creative proposal idea at the racetrack. Whether it is horses or dogs, there are several options for you to choose from. This creative proposal idea can be set up much like the Casino Night Proposal. The only real differences are that it could be an outdoor proposal, during the day, and the attire will most likely be different.

First off, let’s make sure this is the right proposal idea for your lady. Hopefully if you are considering this route, she is a fan of the races or at the very least likes to go out and place bets. If neither of these things are her cup of tea, then you may want to consider another idea. But if she is, then you are going to be golden. A side note, I am not as familiar with greyhound racing as horse racing, so the majority of my focus will be on the ponies.

One consideration for the racetrack proposal idea is to make sure the track schedule fits into your time frame. Ultimately, the race schedule will dictate when you are able to do it. There are some really cool times that you can plan this event. The triple crown races are all big events where you can get away with dressing up and not tip her off. The Breeders Cup is another great event for your proposal.  Obviously these races for the most part are daytime events.  I personally like daytime proposals because you have the entire day to “celebrate” and she has the opportunity to show off immediately instead of potentially having to wait overnight to tell everyone.

So let’s get this party started.  First off, you must know that this is not going to be the least expensive marriage proposal.  Between the track tickets, betting, buying the right clothes, and most likely having two nice meals out for the day; you are going to spend a decent amount of change.  You don’t have to have a plan wired super tight for this day, so that is good, but you will need to have a solid plan for how it is going to go.  Your first order of business is deciding on the event.  Assuming you have that already picked out, then you can decide how you want to proceed with the rest.

Since the Kentucky Derby is the pinnacle of horse racing and marrying your lady should be the high point of your life to date, then let’s pretend that is your choice.  If you are local then you don’t have to worry about lodging, but staying in a nice hotel sure would add a nice touch to your proposal day.  I would recommend staying at the Galt House Hotel.  Not only does it offer great views of the mighty Ohio river, but it also houses Rivue, which is a fantastic revolving fine dining establishment.  But wait, there’s more!  (I’ve always wanted to say that)  Since you are staying in downtown Louisville, you can even set up a romantic carriage ride that evening.  This plays perfectly into your day at the track theme.  Keep in mind that these rooms are not going to be cheap and will be gone way in advance, so the Derby is one you will need to plan for in advance.  Other racing events will not be so bad though.

Now that you have your room reserved, let’s move on to your preparation for the actual day of the proposal.  As we discussed in the Casino Night Proposal post, you shouldn’t take her on the date of her life and expect her to wear her regular clothes.  She will need all new threads to wear for the day.  I recommend a dress, some shoes, and in the case of the Kentucky Derby, she has to have a fancy hat.  Good luck picking that one out on your own.  If you are not keeping the day (other than the proposal part) a surprise, then you should without question have her involved in the picking out of these items.  If you are keeping it a secret and want to buy all of the items for her, I suggest keeping them very simple and possibly having a couple of options for her to choose from (keeping the tags on them to return the one she does not want).  For more details on picking out an outfit for a daytime date, check out our post.

You have the clothes, you have the room, now you need to get your tickets.  You actually probably want to do that first, since the other two don’t happen if you don’t go to the race.  Getting tickets to the races is an easy task, but can be hard on the wallet.  Again, focusing on the Kentucky Derby, you have several options to choose from.  Some of them can be really fun and exciting to use if you are going as just the two of you and others can be great if you want to involve your family and friends.  There is the famed millionaires row where you can be seen with celebrities, or you can rent your own suite.  Churchill Downs also offers cool event activities like trophy presentations, where you can have a race named for you (usually reserved for groups, but money talks) and you can be in the winners circle for the presentation.  You also are invited to join the saddling of the horses in the paddock area.  Now let’s not kid each other, you are not going to get this type of event for the Kentucky Derby…or most races during Derby week, but if you are going other times of the year, these types of things can be much more affordable.

A couple of things to consider about your reservations.  Outdoor seating is almost always available and fairly cheap.  I would discourage you from attempting a marriage proposal in the infield unless you want to run the risk of having mud or poo slung at you at some point.  Stadium seating is nice and can provide a wonderful atmosphere for viewing the races.  Some boxes are outdoors, but covered, so you can be protected from the weather for at least part of the day.  Other boxes / suites are indoors and seats inside them can be purchased individually or by groups.  You can customize your day in many ways depending on whether or not you want to be alone or part of a group.  Personally, I would always choose a one on one marriage proposal because I am a hermit, but many people are social and would find the group setting exciting.  And how cool would it be to propose to your lady with Kid Rock across the room from you when you did?

One final note about your day at the track.  Many races, specifically the Derby are in the spring.  I have seen it blistering hot on Derby day one year and sleeting the next (welcome to KY weather).  So if I were going to do this, I would reserve an indoor suite or use one of the large rooms with access to a balcony.  That way all of your bases are covered and you have a foul weather plan.

Now that the day is planned, you have the room, the clothes are in the bag, and your stay is booked; all you have to decide is when and how you want to propose during the day.  Keep your plans loose unless you have a race named for you already and you plan on doing it in the winners circle.  You never know when you are going to be too nervous to do it.  You also never know when she is going to be in a bad mood because Horsey Longjohnson didn’t win and she had just bet on him.  Just don’t wuss out all day.

This is an exciting creative proposal idea and if you are thinking of trying it out, please reach out to us and let us know.  We would love to help.

And for the love of all things holy, stop what you are doing right now to tell her how much you love her by sending her a bouquet of flowers.

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