Casino Night Proposal

Casinos are a great place to propose to your lady for many reasons. They carry with them an aura of excitement and danger with the promise of a great payoff at any moment. Marriage proposals are not that much different. Combining the two can make for an wild night…and one neither of you hopefully will ever forget.

For some people, going to a casino is not a big deal because there is one (or many) near where they live.  Unless your lady just loves to go all the time, then this may not be the right proposal idea for you.  But if you are like me, and there are not many casinos near where you live, then a casino proposal might be a perfect way to take the biggest gamble of your life.

Setting this up can be pretty easy.  I am sure you can make it very elaborate, but I think just a very special night out capped off with a wonderful proposal can be the best way to go.  If this was going to be my proposal to Bekah, I would start by getting in her closet and finding out what her dress and shoe sizes are.  Then I would start shopping for a “little black dress” for her to wear that night. Once you find the perfect one (more on that later), then you want to find a proper box to put it in. For a night this special, you want to make sure it is done in style all the way around. I recommend a dress box to make it even more special.

Anatomy of an Evening Outfit

Click here for our guide to building a date night outfit.

If I were in your shoes, I would also take the opportunity to buy some nice lingerie for the evening as well.  Just make sure you buy something that matches the dress (strapless, matching color, etc).  The trick is to make her feel sexy and build some romantic tension all night long.

Of course, you cannot forget the shoes.  Again, just head into her closet to find out her size.  It does not matter if she already has several pair of shoes in the color you need (most likely black) because she can never have enough shoes.  Of course you know your lady much better than I do, and if she is the type never to wear heels, I would not buy some 6″ stilettos.  But again, just make sure you buy ones that match her outfit.

Now she will need some hardware.  You will certainly be bringing the real hardware with you for the proposal, but a nice necklace and/or a pair of earrings are things you can buy for her to wear with her new dress.  Plus, you can do your best to match it to the ring you plan to give her later.

Lastly, she needs someplace to keep her lipstick and whatever other crap they carry in their purses.  For a night like this, she can’t simply have a purse, it has to be a clutch.  I know to us neanderthals it sounds like a car part.  Unfortunately it is not a car part, but is as essential to an evening outfit as a clutch is to a manual transmission.  For more details on putting together a date night outfit, check out our Anatomy of a Date Night Outfit page.

One note for you to always consider when buying clothes for your lady.  Unless you have a great eye for fashion, I recommend running your purchases by one of her friends or at least one of your female friends before you actually wrap it all up for her.

James Bond Tuxedo

image courtesy of

Now that you have her outfit all taken care of, it is time to take care of yours.  Personally, I would go with the James Bond look.  I’ll admit I have always wanted a fitted suit…not one of those adjustable jobs you rent, but a tailored suit / tuxedo.  Granted, I do not and probably never will be shaped like James Bond, but it would be nice to feel like it for one night.  I doubt I would go for the tuxedo look because I would only wear it once, but a nice suit can be worn several times.  Jos. A. Bank is a great place to start online if you do not have a local place to get a suit tailored.  If you want to accessorize, you can get yourself a watch, hat, or a cane if you are feeling really fancy.  If even a suit is too much for you, I personally recommend checking out Kenneth Cole for some nice pants and shirts.  You don’t have to spend $10k on a custom fitted tuxedo or suit, just make sure your shoes shine.

Getting the clothing out of the way gives you time to start getting the night arranged.  Most of this can be done fairly simply.  You can go it alone with just you and her or you can ask a friend and his lady to double date with you.  I think either way is fine.  Having another couple with you takes some of the pressure off, as she can have someone else to talk to and hopefully there won’t be any awkward silences because you are nervous.  But being alone gives you the romance and privacy you might want if that is what you are going for.  Whatever you choose should be great.

Remember, this is a magical day for her.  Most women dream of this day their entire life, so take some time to make the entire day special.  Planning it on a Friday is awesome because you can have flowers or chocolate sent to her at work that morning with a note that says you have a date planned for her tonight.  Just before her lunch, you should have her friend meet her at the office and take her to get a mani/pedi for lunch.  If you choose to do this as a double date (you will read more about that in a minute), then this friend can be the same one that is going with you that night…as long as you trust her not to spill the beans.  Later in the day, you can send her some romantic texts.  These will keep her excited about the evening all day long.

If you already live together, then you can have her outfit ready for her at the house.  You can make it a point not to be home when she gets there and just tell her something came up and you have to pick her up at X:XX.  Give her time to take a shower and shave her legs or whatever other things chicks do to get ready for a nice night.  The LAST thing you want is her feeling self conscious all night because she is stubbly.

A limo would be a nice touch, but not necessary.  If you drive a truck with big knobby tires or she just hates your smelly car, maybe you could rent a nice car or SUV for the night.  There is something to be said for rolling around in a clean car that makes things feel better.  Pick her up with your friends in the car already (you should get ready at his place if you are doubling).  If it is just you, then you will be alone, but you should still get ready somewhere other than your place.  Let her get ready alone to build the excitement and anticipation.

Side note, you don’t have to have some sort of Marvin Gaye / Barry White playlist set up (though that would be cool), but try not to play any crazy music in the car on the way to dinner.  No Rage Against the Machine or anything like that.  And also, if you have ever been accused of having road rage in the past, make a mental note to drive the exact speed limit (most all rentals are going to have cruise control) and be the most courteous driver ever.  Don’t foul up your night by ticking her off with your aggressive driving.  Everything about the night should be calming for her.

Formal table setting

image courtesy of Classy & Fabulous

Take her to dinner at a place that requires a reservation and has more eating utensils than you have power tools.  You know the kind, where the waiter pulls out your chair for you and places your napkin in your lap.  When you make the reservations, give her PLENTY of time to get home from work and get ready for the night.  You know she will take forever, so it is probably also best if you tell her the reservations are 15-30 minutes earlier than they really are.  In fact, this is probably a good practice to get into for the rest of your life since most women are 15 minutes late all the time.  But remember, it isn’t the end of the world if she is running late.  Text her when you are leaving to pick her up, and if she is running late, you can call the restaurant and let them know.  Most of them will be accommodating.

I would reserve a room (or suite) at the casino hotel for the evening (if this is a double date, your buddy gets his own room).  If you guys and gals gamble enough during the night, you may even get your room comped by the casino.  How awesome would that be?  Call ahead of your stay and ask the hotel manager if they can set up a romantic evening in your room.  Choose what you want, rose petals on the floor / bed, candles, music, etc.  I am not sure how much they will be willing to do.  This is another good reason to take another couple as a double date.  You can tell them how you want the room to look and they can sneak up there during the night and get it ready for you.  Once they text you that it is ready, you can start working on calling it an evening so you can head back up to the room and get ready to pop the question.

Neil Lane Engagement Rings - Jared The Galleria of Jewelry
How you actually ask her can be up to you.  If you want to do it publicly, then in the middle of the casino floor could be your place.  You could play craps all night until you win big.  Then instead of asking her to blow on the dice for a lucky roll, you can get down on one knee and ask her to make you the luckiest man alive.  If you want it to be private, then you can have your buddy place the ring box on the center of the bed so that when you get back to the room, it is sitting on the bed in the center of a heart of rose petals.  Or you could have him spell out “will you marry me” in rose petals on the bed or the floor and you can let her in the room first.  As she turns around in surprise to ask you what is going on, you can be on one knee.  Again, at this point, you can hardly mess it up unless you say something just totally foolish.

Do you want to try this creative proposal idea and want some tips to help you pull it off? Email us and we will do what we can to help.

Lastly, while you are feeling romantic, show her just a fraction of how much you love her by sending a bouquet of flowers tomorrow. You will be the biggest stud she knows.



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