^^^
My SO is also in finance. He works for a prop trading firm here in Chicago.
Trust me, he will not take the time to research anything or to figure out what's "me." He is just not that kind of guy, although he is fantastic in many, many ways. He will buy the first ring that his eye falls upon that is remotely appealing to him and fits into his budget. He'll probably buy it in the first store he walks into.
To get a ring that I would even remotely want to wear (because after all, if an engagement is about the meaning, isn't the ring just an accessory? and what's the point of wearing an ugly accessory? I can just buy a nice ring and wear it myself in that case!), I would just pick it out myself and buy it with his credit card. It's deeply unromantic. But that's just really how he is -- he hates wasting time on anything that's not related to something of deep interest to him. Unfortunately, his interest does not include diamonds.
So seriously, a ring is all on me! Which is why I very much appreciate the opinions and loose guidelines you ladies have presented here.
Ooo icic..haha..i understand..im am sure your bf is a wonderful man who loves u very very much, and working in finance is very stressful so its understandable...i see where hes coming from..haha....
do u have a diamond district in Chicago? maybe you can go w/ a good friend (dont go alone) and take a look..see what the designs, options, prices are..get a good idea..try some on to see your RING SIZE and also what shapes you like and looks good on your hand...figure out the setting you prefer..its important to do research first b/c some places will totally try to rip you off if you are not an"educated consumer." also, does any of your friend have diamond brokers? or maybe jewelers they trust? often, these pp can get u a good % discount..at places like Tiffanys and Harry Winstons, diamonds are marked up sooo much, that unless you are crazy about their designs, its probably not worth it..you can get a really quality diamond elsewhere too..just have to look harder..
also, have u tried blue nile online? they have a good tutorial on diamonds, 4cs, etc...its a good read..that way if and when you are negotiating prices, you have a reference and know the market price..
maybe if you do all the research first (finding out ring size, or maybe even ur dream ring) you can just tell your BF outright when the "time" comes..lol..that way, its a win win situation! you get the perfect ring, and he buys the perfect ring w/o any headache or time wasted! haha
i think my husband and i are a bit odd compared to most couples, he always buys gifts for me on his own and i completely trusts his taste..lol..he always picks things i love..but whenever it comes time for me to buy him things..omg, its the HARDEST! hes an impeccable dresser...and im not so educated or informed on mens fashion (im so used to getting things for my dad from Brooks Brothers, but my husband HATES typical American men clothes!) so buying things for hubby has always been quite hard for me..haha..its gotten so bad that i just call his tailor here on Madison and ask him to make the latest order my hubby placed and i just pay for it ....Not romantic on my part..i know..but what can i do? haha

Good Luck Intlset! shopping for e rings can be complicated, i hope to help if i can!!