I spent 6 weeks educating myself before buying a diamond and am now engaged. Here's what I learned (contrary opinions are also appreciated):
1) Buy a round brilliant (RB)
If you or your girlfriend fall in love with fancy cuts, then go for it. But nothing will reflect more light than an RB, it holds value the best, and looks great in every imaginable kind of setting. If you want to do something different, I'd recommend playing with the setting or with sidestones, and sticking with RB.
2) Get a great cut, a good color and eye-clean clarity, then figure out what carat you can afford
I decided I wanted an RB AGS000 H&A. I don't really care about the hearts (you can't see them after it's mounted), and the arrows are pleasant but not essential. But H&A is really about a level of craftsmanship and precision that creates the best possible diamond out of the rough stone. Click on the GOG tutorial, plus the rough diamond and ideal cut buttons on the ISEE2 website to show why ideal cut matters. There's no more ideal than H&A. (But be sure to note that lots of stones that claim to be H&A are not. You don't have independent certs like you do for AGS000, so make sure that it's a complete, symmetrical H&A pattern.)
http://www.goodoldgold.com/ags_000.htm
http://www.goodoldgold.com/hearts_and_arrows.htm
http://www.isee2.com/isee2flashindex-us.htm
I wanted VS2 so that it would be truly eye clean even in a large diamond. Unless you get pleasure out of knowing that your diamond is flawless, I see no value on going better than VS2, since nobody wears a loupe or a 70x microscope near their diamond. I decided on F, as I wanted to have a "colorless grade", but couldn't see the difference to D once it's set. I was fortunate enough to have a decent budget for the stone, but thought my girlfriend would be self-conscious with a diamond much bigger than 2 carats.
I decided on a 2.03 F VS2 AGS000 H&A from Good Old Gold (GOG). http://www.goodoldgold.com/2_03ct_f_vs2__h%26a.htm.
If I had less money to spend, I would have gone to a G or H and SI1 (or even SI2), as long as it would be eye clean or the inclusion would be covered by a prong. Note that AGS000 H&A 1 carat H SI1's are available on pricescope at $4 K, and 0.7 carat at half that. I suspect my fiancée would still have been thrilled with either. Most people can afford to buy a much better cut stone than they would ever find through a regular brick and mortar (B&M) store.
3) Buy a great cut and don't worry about brand
Obviously, if your girlfriend has ever told you that she always wanted a Tiffany diamond, than buy her a Tiffany diamond. But realize that you're overpaying by at least 30%, and that, despite reputation, Tiffany sells some fairly mediocre stones (good cut and symmetry, medium fluorescence).
My metric is that diamonds are a commodity and that every aspect of a commodity should be independently evaluated. One B&M jeweler told me that you can't trust what a cert says, because you need "jeweler's eyes". That was the last time I went into his store.
There is a simple distinction between branded and unbranded H&A's, vs. Tiffany's, vs. AGS000 and other stones. That is, if you send the stone to an independent appraiser, they can never determine the brand and so there's no intrinsic value in brand (beyond what you as a consumer assign to it). By contrast, triple ideal and H&A are intrinsic qualities of the stone that make it a look better, especially since cut is the most important of the 4 C's.
The only possible option better than AGS000 H&A is Eightstar, which is verifiably different than a regular H&A. If you see one and fall in love with it, than go for it. But note that many viewers do not prefer their look, and that you're paying 30% to 50% more for a level of precision that is hard if not impossible to see in real life. And, new tools such as the Brilliantscope and ISEE2 show that some Eightstars do worse than many H&As in the objective characteristics of fire, brilliance, and scintillation that many viewers prefer.
I bought from Good Old Gold because Jonathan has built himself a fantastic niche between the low-end H&A brokers who provide you no info on the stone ahead of time and the branded H&A vendors where you pay a premium for their guarantee that the stone is good. With GOG, you get the confidence of a great rock without having to pay for an ultimately meaningless brand. The best thing about GOG, of course, is that nobody provides more and better information about the exact stone you're planning to buy. If you want the best possible information about what you're buying, at a reasonable price, and with great customer service, I highly recommend GOG. (And, someday Jonathan will update his circa 1995 web site design, and remove the only blemish on his buying experience.)
4) Fluorescence is good at H and higher and bad below
If I were getting an H or worse color diamond, I would definitely want strong fluorescence, as the blue plus yellow appears white in many lights. But, with a "colorless grade" F, I wanted a pure white and no possible blue glow. I found out that another B&M store was trying to sell me a strong blue fluorescent stone only after asking them to fax me the cert. The delay almost screwed up my hotel reservations for when I was planning to ask my girlfriend to marry me. It also convinced me to buy online, where I could find out everything about the stone before I bought.
5) Let her pick out the setting
I went with the simplest (and cheapest) Tiffany-style 6 prong in white gold to be able to put it on my girlfriend's finger when I surprised her with the proposal. We're now looking together for the permanent setting she wants. She is growing attached to this one, so we may just swap it out for one in platinum. But since she we're hoping for her to wear it for the rest of her life, I felt she should be involved in the setting decision.
6) Buy what can you afford and no more
The 2 month salary rule seems reasonable if you and/or your girlfriend are a fan of diamond engagement rings. However, you'll probably both be much happier with a slightly smaller stone than getting a bigger one and finding yourself with a lot of arguments about credit card debt.
Good luck!

1) Buy a round brilliant (RB)
If you or your girlfriend fall in love with fancy cuts, then go for it. But nothing will reflect more light than an RB, it holds value the best, and looks great in every imaginable kind of setting. If you want to do something different, I'd recommend playing with the setting or with sidestones, and sticking with RB.
2) Get a great cut, a good color and eye-clean clarity, then figure out what carat you can afford
I decided I wanted an RB AGS000 H&A. I don't really care about the hearts (you can't see them after it's mounted), and the arrows are pleasant but not essential. But H&A is really about a level of craftsmanship and precision that creates the best possible diamond out of the rough stone. Click on the GOG tutorial, plus the rough diamond and ideal cut buttons on the ISEE2 website to show why ideal cut matters. There's no more ideal than H&A. (But be sure to note that lots of stones that claim to be H&A are not. You don't have independent certs like you do for AGS000, so make sure that it's a complete, symmetrical H&A pattern.)
http://www.goodoldgold.com/ags_000.htm
http://www.goodoldgold.com/hearts_and_arrows.htm
http://www.isee2.com/isee2flashindex-us.htm
I wanted VS2 so that it would be truly eye clean even in a large diamond. Unless you get pleasure out of knowing that your diamond is flawless, I see no value on going better than VS2, since nobody wears a loupe or a 70x microscope near their diamond. I decided on F, as I wanted to have a "colorless grade", but couldn't see the difference to D once it's set. I was fortunate enough to have a decent budget for the stone, but thought my girlfriend would be self-conscious with a diamond much bigger than 2 carats.
I decided on a 2.03 F VS2 AGS000 H&A from Good Old Gold (GOG). http://www.goodoldgold.com/2_03ct_f_vs2__h%26a.htm.
If I had less money to spend, I would have gone to a G or H and SI1 (or even SI2), as long as it would be eye clean or the inclusion would be covered by a prong. Note that AGS000 H&A 1 carat H SI1's are available on pricescope at $4 K, and 0.7 carat at half that. I suspect my fiancée would still have been thrilled with either. Most people can afford to buy a much better cut stone than they would ever find through a regular brick and mortar (B&M) store.
3) Buy a great cut and don't worry about brand
Obviously, if your girlfriend has ever told you that she always wanted a Tiffany diamond, than buy her a Tiffany diamond. But realize that you're overpaying by at least 30%, and that, despite reputation, Tiffany sells some fairly mediocre stones (good cut and symmetry, medium fluorescence).
My metric is that diamonds are a commodity and that every aspect of a commodity should be independently evaluated. One B&M jeweler told me that you can't trust what a cert says, because you need "jeweler's eyes". That was the last time I went into his store.
There is a simple distinction between branded and unbranded H&A's, vs. Tiffany's, vs. AGS000 and other stones. That is, if you send the stone to an independent appraiser, they can never determine the brand and so there's no intrinsic value in brand (beyond what you as a consumer assign to it). By contrast, triple ideal and H&A are intrinsic qualities of the stone that make it a look better, especially since cut is the most important of the 4 C's.
The only possible option better than AGS000 H&A is Eightstar, which is verifiably different than a regular H&A. If you see one and fall in love with it, than go for it. But note that many viewers do not prefer their look, and that you're paying 30% to 50% more for a level of precision that is hard if not impossible to see in real life. And, new tools such as the Brilliantscope and ISEE2 show that some Eightstars do worse than many H&As in the objective characteristics of fire, brilliance, and scintillation that many viewers prefer.
I bought from Good Old Gold because Jonathan has built himself a fantastic niche between the low-end H&A brokers who provide you no info on the stone ahead of time and the branded H&A vendors where you pay a premium for their guarantee that the stone is good. With GOG, you get the confidence of a great rock without having to pay for an ultimately meaningless brand. The best thing about GOG, of course, is that nobody provides more and better information about the exact stone you're planning to buy. If you want the best possible information about what you're buying, at a reasonable price, and with great customer service, I highly recommend GOG. (And, someday Jonathan will update his circa 1995 web site design, and remove the only blemish on his buying experience.)
4) Fluorescence is good at H and higher and bad below
If I were getting an H or worse color diamond, I would definitely want strong fluorescence, as the blue plus yellow appears white in many lights. But, with a "colorless grade" F, I wanted a pure white and no possible blue glow. I found out that another B&M store was trying to sell me a strong blue fluorescent stone only after asking them to fax me the cert. The delay almost screwed up my hotel reservations for when I was planning to ask my girlfriend to marry me. It also convinced me to buy online, where I could find out everything about the stone before I bought.
5) Let her pick out the setting
I went with the simplest (and cheapest) Tiffany-style 6 prong in white gold to be able to put it on my girlfriend's finger when I surprised her with the proposal. We're now looking together for the permanent setting she wants. She is growing attached to this one, so we may just swap it out for one in platinum. But since she we're hoping for her to wear it for the rest of her life, I felt she should be involved in the setting decision.
6) Buy what can you afford and no more
The 2 month salary rule seems reasonable if you and/or your girlfriend are a fan of diamond engagement rings. However, you'll probably both be much happier with a slightly smaller stone than getting a bigger one and finding yourself with a lot of arguments about credit card debt.
Good luck!
