You will get the most money selling it yourself through eBay or exboyfriendjewelry or local buyer etc. Your second best will be to put the ring on consignment at a good local mom and pop jewelry store. After that the value drops dramatically.
The markup on diamonds has dropped dramatically since the internet started making them a commodity. What used to be a 4x to 5x markup is now 2x. If you think 2x is high, look at Starbucks. The design, the art, the emotion has zero value.
If you decide to sell look at price listings at a site like Pricescope to see what new, unset, diamonds are selling for at bottom retail. If you can get 40% of that you are doing great because the seller is already buying at 50% to 60% of that price so anything more than 40% means it would be easier to just buy from his normal supplier rather than deal with an off the street buy.
Diamonds and jewelry are NOT investments. They are luxury items. Very very few things maintain their value once you walk out of the store with them. Cars, boats, airplanes and so on. Luxury items. To think you can sell it back for anywhere near what you paid is unrealistic to begin with. And one last thing. If anyone that tells you a diamond is an investment, run.