The Rules of Proposing

We’re getting to that age where people are starting to get married so, in the spirit of camaraderie and ignoring the fact that I am hopelessly single, I have decided to put together the “3 Rules for Proposing”:

1.) Pick out a ring unique to her 

No, it doesn’t need to be some huge rock that’s gonna break our wrist; we’re realists.  We know you’re no Warren Buffett, we love you for you.  What we are looking for is a ring that shows how much you know us.  It had better fit perfectly on our finger like Cinderella’s glass shoe or, best believe, we will have a moment of doubt when it has difficulty sliding over the knuckle bone.  Pay attention to your girl’s likes and dislikes.  Take me, for example.  I rarely wear silver and protruding jewelry often gets caught in my ferociously curly hair.  Therefore, the engagement ring I get ought to have gold undertones and several demure diamonds instead of one large one.  Pay attention.

2.) Treat her to an impromptu spa day beforehand

As females, we are notoriously vain and we want other females to know how much better we are than them.  This means that as soon as we get the rock, we are going to have to take a photograph of it on our hand, and if we look down and see chipped nail polish, we are going to be devastated.  Yes, in an ideal world, your girl will keep her paws and claws perfectly manicured at all times, but, let’s be real.  If she’s worth wife-ing up, she probably has a decent job and is therefore at work on most days when the salon is open.  Do yourself a favor, just in case, and send her and her best girlfriend to an all-day spa treatment the Saturday before.  It’s the gentlemanly thing to do.

3.) Know who you’re proposing to

Knowing the woman that you’re going to spend the rest of your life with is key when deciding how to propose.  The proposal sets the tone for the rest of your relationship, as well as whether or not she says yes.  Below are the types of women and what to watch out for when proposing to them.  Every woman fits into one or more of these categories, so take bits and pieces as you will:

– The Superficial Woman

Pomp and circumstance is important, as is avoiding any major holidays.  Your proposal cannot take place within two weeks of any of the following holidays: Halloween, Thanksgiving, Christmas/Hanukkah, New Years, Valentine’s Day, Easter, Mother’s Day, Father’s Day, 4th of July, and her birthday.  The sole exception for this is if you start off your proposal explaining that the reason you chose this date is because it has some sort of significance to your relationship, and it better be good.  Public places are usually good for this one; she wants it on Youtube.

– The Shy Woman

Avoid all public proposals.  She doesn’t like to be put on the spot, and even if she is madly in love with you, this will embarrass her.  Choose something sweet and endearing which reminds her why she fell in love with you in the first place and shows her how great the rest of her life would be with you by her side.

-The Skittish Woman

She was hard to lock down in the first place, so don’t rush the proposal.  She cannot be surprised by it; she needs to know it’s coming beforehand so that she can prepare herself mentally.  On the offhand chance that you did not drop enough hints or you were wrong about her state of ‘readiness’, avoid public places as well.

– The Insecure Woman 

She’s so happy to be with you, but is constantly waiting for the fantasy to collapse all around her.  Avoid joking proposals.  These need to be as sincere and thought-out as possible.  Your aim is to make her confident in the status of your relationship, shown through an intimate, meaningful proposal.  A great example would be a date that takes her through the highlights of your relationship thus far, culminating in a grand, sweeping, one-knee-on-the-ground ring presentation.

– The Aggressive Woman

She’s been dropping hints to you left and right for the last few weeks, letting you know that you’re the one she wants to marry.  Pomp and circumstance isn’t really that important to her, but she doesn’t want to risk emasculating you by asking you herself.  Spur of the moment proposals work best with this woman, because she loves the idea that you were just looking at her one day, sitting next to you in sweatpants and a carton of Chinese food sandwiched between her legs, slurping lo-mein with chopsticks, and you suddenly knew that she was the one you had to be with.  For this one, sometimes you don’t even need a ring to propose; that can come after.

My favorite proposal is from He’s Just Not That Into You, and is an example of how a man should propose to a woman who embodies Aggressive, Insecure, and Shy:

Good luck with wedding season, fellas.


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