1. Learn about diamonds the right way.

Most men know very little about diamonds when they start shopping for an engagement ring.  Most try to educate themselves through people who are trying to sell them diamonds.  That is the fastest way, but definitely not the best.

I may be able to point you in the right direction, but there is no amount of information that I can write or that you can read that will educate you about what gem-quality diamonds are really about.  I recently read a thesis from an MIT grad who had analyzed online diamond prices and created a formula for obtaining the highest value diamond for your money.  I am sure his fiancée loves her diamond, as well as the effort he put into finding one for her.  However, many of his conclusions were completely wrong.

The educational content you will find about diamonds online is mainly for the purpose of selling them. Ideal Cut diamond is the name of a cut. It is a smart name from a marketing perspective, in the same way that the "Court Efficiency Act of 2013" was marketing a law that isn't entirely about efficiency. The four C's are a sales tool to make you more comfortable buying. Ask around and you will find few women who can tell the difference between different clarities or colors of diamonds... nor do they care.

Do yourself a favor: get out in the real world and and start looking at the diamond jewelry that women around you are wearing. This is how women have learned to love diamonds ever since they were children. Ask your friends, family members and co-workers about the pieces they like, the histories behind them, and why they like them. Compliment women's jewelry and, sometimes, they will tell you about it. The story behind the piece is just as important as the way it looks.  Women love diamonds because of the way diamonds make them feel.  Women who don't love diamonds dislike them for the same reason.

Once you understand what makes women love diamonds, you will do a much better job of searching for one that your girlfriend specifically will love.

So many men read the "diamond education" page, slide the arrow along the clarity scale, and crunch the specs together to buy the "perfect" diamond without ever seeing it. That's the quickest way to buy a diamond, but hardly the most romantic.

2.  Make it a romantic experience.

Generations of peers, family members, and marketing have given diamonds an allure that is unmatched in other industries.  Engagement rings and weddings are a cultural experience that we learn about in kindergarden.  Almost everything about an engagement ring is romantic - except for the task of buying one.

If you want to surprise her, trying to figure out what your girlfriend wants in the engagement ring can be difficult.  Men don't normally pay close attention to their girlfriend's taste in jewelry.  Furthermore, their taste in jewelry can change significantly between costume, fashion, and fine jewelry - as well as everyday wear vs. occasional wear.  Some women already have an idea of what they want in an engagement ring.

There is also the cost. Fine jewelry (especially diamonds) can be expensive.  

Don't let these hurdles take away the romance of the experience. Most women are more interested in you proposing than the size of the diamond or the style of the ring. The romantic experience will be better for both you and her if you can keep the engagement ring buying experience as romantic as possible.

3. Decide whether to buy online, from a jeweler, or a diamond dealer.

Here is a food analogy:  Before my girlfriend and I have dinner together, we decide whether to go to a restaurant, cook, or order in.  The food is going to be different via each method.  After we've made the former decision, we then decide what to eat or where to go.

If you buy from a jeweler, you will usually get a better product and pay more for it.  Jewelers will spend more time with you learning what will be best for you and your girlfriend.  You have to pay for that time, as well as the overhead required to run a brick-and-mortar operation.  However, your jeweler can also find out more about what you're looking for.  If you are honest about your budget and you go to a jeweler who can work within your range, they will be able to find you the right price diamond for your budget.

If getting engaged is all about the diamond and the ring is just a holder for the diamond, you might want to buy from a diamond dealer.  You will be able to see much more product in person, and choose based on what is in front of you. Make sure you have someone who will set the diamond into a ring for you - not all jewelers will set diamonds supplied by customers.

If you are either extremely busy or don't care much about the ring itself, buy online.  If you buy online, you will save time and get more product and less service for your money.  If you are buying an engagement ring (rather than just a diamond) it will usually be mass-produced on a large scale, so you you will find less interesting product and, obviously, less flexibility coupled with lower prices.

Which leads us to….

4.  Don't obsess about the specs.

Men love numbers.  Women love feelings.  Men are as interested in diamonds as women are in automobile engines.  This is a massive generalization, of course.

The four C's, the spreadsheets, the refractory angles, the boutique tools for measuring fire or cut - they're mathematics, developed to help market to men.  Even though analyzing numbers isn't particularly fun (unless you work in finance), most men will buck up and crunch the numbers because they think that's what they're supposed to do. Women rarely care about the mathematics side of diamonds.  They care about how the diamond makes them feel.  

Crunching the numbers is a good way to find an average diamond.  As stated in Tip #1, pretend you're a woman for a bit and learn about diamonds the right way.  The only number that is important in a diamond is the wedding date you set after your girlfriend says yes.

5.  Know what you want and be honest about what you want.

What you want does not have to be very specific, but if you are honest about it, your jeweler will know where to start.  If you're looking for a diamond engagement ring and don't know your design, metal, or budget yet, let your jeweler know.  They will ask the questions necessary to help you narrow down your options.  If you've been searching online and think you want a 1ct. G VS2 diamond at a specific price and are shopping around just in case you can find a better price, let them know exactly that.  They can respond much more efficiently and explain the pros and cons of your alternatives. Even if you're looking only for engagement rings under $100, most jewelers could tell you where to go. 

If you are not upfront about what you want, you're wasting your jeweler's AND your own time.  Be aware that your diamond dealer or jeweler is at work, on the clock. You will get much better service if you are a considerate customer.

It is also essential that you are honest when shopping for a ring.  Some people think that by leaving information out or lying, they can somehow gauge the jeweler better.  Some people are paranoid that if they disclose their budget, the dealer will just change all their prices on the fly.  More likely is that you tell your vendors your budget, and they will show you options that you can afford. Duh.

I don't want to be preachy, but so many men get this wrong.  So preach I will:

Men are often paranoid that they're getting ripped off by a jeweler or diamond dealer.  This reputation, unfortunately, has been legitimately earned by the industry  - especially gemstone dealers.  However, the paranoia is often a self-fulfilling prophecy.  Men who are convinced that everyone is charging too much for diamonds will more likely buy from someone offering a great price. That "great price" is usually an inferior diamond.

Honest jewelers don't want dishonest customers, and especially don't want dishonest repeat customers. If you hope to find a jeweler who offers such good product and service that you will want to come back, you need to be a good customer.  If you first give your jeweler a budget that isn't really your budget, you are making them work needlessly.  If you hope that a jeweler will match the price of an online mega-dealer, you are wasting everybody's time.

6.  Don't buy a diamond that you don't know how to set in a ring.

Be careful about bringing a diamond you bought online or at a diamond dealer to a jeweler to set in a ring.

It seems like the best of both worlds - cheap diamond, nice ring - but jewelers will often turn you away.  If they accept the work, you may pay more for their work and/or not get their best efforts.  I have picked up several customers because they bought a diamond and couldn't find any other jeweler willing to set their stone.  I am usually willing to set your diamond - but I do charge a "corkage" fee for this service.

Many men figure that they can buy a diamond cheaper online or from a diamond dealer.  While this is sometimes true, it has three unintended side effects.  First, it lets the jeweler know that you are cheap.  Second, it changes the profit margin enough that sometimes, it isn't worth the jeweler's time.  Third, you don't know anything about diamonds.  Very often, you will bring in a diamond that is below the jeweler's standards and can cost the jeweler more time to work with because of the lower quality.

I like this food analogy:  Let's say you go to a restaurant with a bottle of wine.  They charge a corkage fee.  That pays for the glasses they have to wash, the time to open and pour the wine, and a little profit.

Now let's say you want to bring in a steak.  How many restaurants would cook up your steak for you?  MAYBE, if you went hunting and brought in the tenderloin of a fresh wild catch.  Certainly NOT if you ask them to discount the price because you are supplying the meat.  And definitely NOT if you are bringing in a steak from Costco.

I understand that many men feel that searching for a diamond is an important part of the engagement ring buying process.  But please, please, please don't think that you will save money or get a better ring that way.  Custom jewelers know more about diamonds and engagement rings than you ever will (or want!) to know.  

If you still really want to buy the diamond separately, here is tip #6 ½.

- Find a jeweler to make a ring for you before you buy a diamond.  That way you won't get stuck with a stone and no one to make you a ring.

- Bring your jeweler fresh wild hunting catch, not a steak from Costco.  A high-quality family heirloom diamond is far more meaningful than a diamond I can buy for you.  A low quality heirloom diamond may be nice for your fiancée but will not be an exciting project for your goldsmith.  A cheap diamond from the largest online retailer is not going to get anyone's mouth watering for your project.

7. Understand that you don't understand the system.

When you shop from a large online vendor, why are there such enormous price discrepancies for diamonds with the same specs? Why are there so few diamonds in the .97-.99ct range?  What are the grading variations between EGL & GIA, (and IGI, AGS, etc.) and within the organizations?  What diamonds end up online, which stay in stores?  What aren't people telling you about the diamonds you are looking at?

Nearly all men interested in buying their first diamond go through sticker shock when they discover how expensive they are. The natural impulse is to research online to find a back door to a better price. I am not trying to be unsympathetic, but... you're not going to cut out the middleman.

Most diamond dealers do two things: buy diamonds and sell them. In 40 hours a week, year after year of buying and selling diamonds, they develop sophistication in the process.  You are lying to yourself if you think you will learn enough about the diamond industry in 5 - 10 hours of research to be able to do anything more than make an informed decision about what diamond to buy.

Want to buy a diamond online?  You're buying retail.  Live in NYC and want to try your luck in the diamond district on 47th St?  Even in the diamond tower, you will be paying retail.  I buy my diamonds wholesale and mark them up to the retail price my same dealers charge to end consumers - for those dealers that sell retail at all.  Any respectable jeweler who specializes in diamond jewelry uses wholesale suppliers.

It is certainly possible that you'll save money by buying from a dealer or online, but that is more often because you will buy a lower quality diamond than a jeweler will want to sell to you.  You don't want to be the naive consumer to whom dealers can unload their unwanted diamonds. (You don't want to be the naive consumer to whom jewelers unload their unwanted diamonds, either.)

This should be obvious, but no retailer is going to "cut out the middleman" and pass the savings onto you. There are pretty much two types of diamonds - market price diamonds and overpriced diamonds.  People may offer a discount on a diamond, but it is usually a game to make you feel better about your purchase.  The only way to get a deal on a diamond is to buy it from someone how has had bad luck in their relationship or finances.  That hardly makes for a romantic engagement ring.

8. Be upfront about what you want and set a budget.

Before you do anything, ask yourself how much you think is reasonable for an engagement ring.  Do you care how much of the budget goes towards the diamond vs. the mounting? (A mounting is a ring minus the diamond.)  Do you want to find the ring with the highest value of materials for the money? Do you want to spend more for a brand name that your girlfriend will identify with?  Do you want your money going toward making your piece unique?

These engagement ring questions are applicable even if you are just purchasing a diamond.   You can try to get the most value for the money by buying diamonds that are plentiful, you can pay more for a brand name or proprietary cut, or you can search for a boutique diamond with unique attributes.

Think about these questions, take a look at what's available and adjust your budget accordingly.  Nearly everyone spends more than they initially thought, because diamonds cost more than most people realize. You will save money if you already have a number in your head in the beginning.

Of course, if money is not an object, you can exceed your budget if you see something you like.  If you are like most men and price is important, you will save everyone time by only looking at diamonds and engagement rings that fit your budget range.