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I would at least go to a jewelry store together so you can try on a few different settings to see what looks best on your finger and to narrow down for him what you like.
Mine was a complete surprise. We had discussed getting married but never the RING. He went home on leave for a week, picked it out all by himself and came home and proposed... I LOVE IT! He knows me well enough to know what would look good on me and what wouldn't... less then a week till the wedding :-)
Mine was also a complete surprise and I LOVED it that way. If you are truly worried, you two can "shop" around for the style you like to give him hints. The only thing that I did was get sized so it was one less thing for him to worry about when he went to buy the ring.
Do you have a good girlfriend, his sister or your sister that can help him? I did that with my SIL! We went together and tried things on together, and she reported back to him what I liked. It ended up being a complete surprise and I love it!
I was also surprised by FI and I adore my ring. I proudly wore it with the ring guard for a week so I could show it off before I could bear to take it back to the jewelers for re-sizing.
Definitely try rings on so you know how they look on your finger. FI wanted to buy me a classic 6 prong round. I went with him to get a feel and rounds looked TERRIBLE on my fingers. We couldnt figure out why they looked so bad. As soon as I started trying princesses/cushion/emerald, we immediately noticed they looked 1000x better - and I ende dup witha cushion (2 years later but still 
) if you arent comfortable going with him, bring a girlfriend who will confide in him what you love and looks best
You should definitely see what looks good on your finger and what's comfortable. Also, a thin band might fit at a smaller size than a thick one. IE i wear a 6 in thin gold bands but i wear a 6.5 wedding band because my band is thick.
Even if you want to be completely surprised, you might find out that you really LOVE a round cut or a princess, or that you dislike the emeralds. There are different kinds of diamonds: do you prefer something shiny (emerald cut) or something sparkly (round). Do you want a pear shape? etc. You don't have to tell him what you want, but you could tell him at least what you don't like. White gold, yellow gold, solitaire, setting, etc. He might be thinking "bigger is better" and you may find that a larger setting or stone overwhelms your finger. It's not like you HAVE to pick it out when you're in the store and it's not like he HAS to buy that particular one. At least when i was trying on rings, there were more "i don't like this" than "i like this" so at least we narrowed down what I didn't want.
But if you want to be 100% completely surprised, definitely send your mom or sister with him. If I was going to be surprised (I picked out my setting but let him pick out the stone with guidance from me. I told him i wanted a radiant and he got me a cushion which is really unique and i love it), I'd only trust my mom to pick it out.
I'm so glad we went ring shopping before - or rather setting shopping since the stone is an heirloom. We got a lot of ideas and figured out what I liked and looked nice. I ended up liking things completely different than I would have chosen just by looking at pictures.
And when he proposed with the one that was my favorite, it was really special and still a great surprise. Having an idea of what the ring looks like does not detract from the moment or the romance of the proposal at all.
On a side note, you don't want the high and excitement of getting engaged and getting married wear off, and the romanticism of "oh he picked it all out just for me!" to wear off and you realize in a year or two that you don't just absolutely love the ring he got you...or that you'd have preferred X, Y, or Z in regards to it. Lots of women love this notion that he picked it out....but you still want to make sure you love it in 5 years, despite the fact that HE picked it out. You want to love it for its aesthetics, too, ya know! I mean, you do get used to wearing it on your finger and while you may love that he got it for you, you may not love love love WHAT he got you down the road. I love my DH, but I don't always love what he buys me sometimes and he doesn't always get my taste in jewelry, so I truly was afriad he'd have gotten me a different ring. I actually asked him in the store "what would you pick for me" and he picked out a princess cut with baguettes on the side and weird little diamonds in the corners. Ick. =]
I think trying on rings is important. If he were to chose what I thought I wanted, it would have looked wrong on my finger. I found out I liked more antique rings in pictures, but they didn't look right on my hand. You don't have to try on rings together, I think it's nice to get a general idea of what you want, and have him take the idea and add his personality in some way.
Mine was a complete surprise. He picked something I never would have picked for myself and I LOVE it. As far as the size, he guessed at that too and it came out just right.
We went ring shopping and I tried a bunch on and I'm glad I did. The ring I always lusted over again and again actually looked odd on my really small hands. The ring setting that I ended up liking was one I had never even considered! So, while I understand wanting the surprise element :) I am glad that I tried on a few. That way he knows my ring size for sure now, too! :)
Ok... thank you!!! You all have been so helpful!! I think that is a a really good idea. I hadn't even thought of it until I started reading some other posts and realized how common it really is to have like a joint- effort type thing doing all the engagement stuff. I VERY much appreciate all of the advice!! :-) Now I'm excited to go shopping... hehe.
@ejs4y8 - You are sooo right! I will have to live with the ring on my finger until the day I die... and it is such a huge investment that it would be kinda dumb not to atlest see what they look like on my finger. So I can know what cuts I like, and styles and stuff.
we shopped for rings and we're both glad we did. i ended up changing my mind on what i wanted. we both decided the initial design i thought i wanted wasn't working and i ended up trying on one of those halo styled rings and we both fell in love. surprisingly, i always liked the look of those rings but didn't think it was me. LOL, boy was i wrong! plus we got to see what size diamond looked best without overwhelming my hand and i was properly sized as well.
the final ring design is up to the bf so i'll still be surprised by what he picks.
I only gave him my size number, so the ring is a complete surprise :) Idk even if he gave me the ugliest ring ever, I would totally love it, because its his love promise to me :)
Well I know he would never buy me an ugly (to me) ring because I've told him what I like on a ring and what I don’t like :)
I think ring shopping is. SO. FUN!!!
Trying on beautiful baubles?! WHY NOT?!?!?
My man and I do everything together so ring shopping just seemed to be the logical thing. The only thing that sucked about it IS: I have been anxious waiting for the ring to appear on my finger!! When we went shopping I wrongly assumed that just because we picked something out that it would happen soon.. Well... Valentine's day went by, my birthday went by, our trip to meet my extended family went by, the 4th of July went by...that's five months and counting. However - maybe now when I get the ring, it will be even sweeter because I've been wanting it so badly.
So - I highly recommend it based on the fact that when I get the ring I'll have a ring I absolutely LOVE, but keep in mind once you pick it out that you will have to wait (in agony) knowing it's coming, but not knowing when!!
Best of luck!
My ring was a total surprise :-) We were together 8.5 years when we got engaged and we never once went ring shopping. He knew the style I preferred, but I never showed him any. He went to the jeweler, designed the ring himself and gave me the most perfect ring! I LOOOOOVE that it was a complete surprise! (The ring AND the engagement!)
My FI was all about surprising me until he did some research and realized how expensive diamonds are!! He didn't want to buy a style that didn't look good on me, so the next thing I knew we were at Tiffany on 5th Ave trying on engagemnt rings. One of the BEST days of my life! And surprised to see that a lot of styles looked way too overwhelming on my extremely small size 3 ring finger.
I never knew anything about engagement rings, nor did I pay attention to what they looked like, ever! Once fiance was ready, we looked a couple times together. I really didn't have a preference at first. Than I realized I hated how a round diamond looks on my hand/finger ... I actually hate round ones on me.
I saw a cushion cut diamond, which happened to be some type of rare yellow stone, and fell in love. I knew that was what I wanted. So fiance knew that and left the rest up to me.
Wait, well we went into the jeweler and had my ring finger sized and looked at bands, like the width and I also let him know I liked how it looked with diamonds all the way around. Everything else, he designed himself with the jeweler.
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Do you all think it is important to try on the rings before he buys it? Because I don't really want to know... and he told me he has this "plan", and he wants to pick it out based on the love he has for me... What if it looks terrible on my finger?