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I asked him what budget I should be looking in then found rings I loved from a few hundred dollars all the way up to the budget that he said. I haven't gotten it yet and I'm very curious to see what he'll end up purchasing.
Pre-Congratulations!!!!!
Maybe just let him know the diamond size you're okay with? Just explain that they always show big diamonds in the rings so you weren't lookng at that, just the settings?
Oooh, how exciting, congrats! Perhaps if you send him pictures that happen to have a huge stone, you can point out the particular of the style that you like, rather than the fact that it's a big rock. Such as "I love how this ring has two side stones", etc. Good luck!
Oh that's so sweet of you to worry about being presumptuous! I think you should go ahead and send all the pics he's asked for. It'll help him in the long run and he's already assured you that you're not being presumptuous 
If you're worried about the stone size, you could pick something that you think he'd be comfortable with financially or send him a couple of different rings w/ different stone sizes that you like.
Have you gone to try on any rings? The reason I ask is because originally I thought I wanted a certain carat size and it turned out to look ridiculous on my small hands, so that is something you might want to do before sending him all the info.
I would just send a few pictures of settings you love and write that and then maybe a few with the shape of diamond you prefer and not even worry about the size of the rock in the pictures include...You're just sending him ideas, most pictures are of rediculous-sized diamonds anyways so I doubt he's going to think you expect a 4 carat monster or anythingv when you include pictures of rings you like...SOOO exciting, you have to post a pic when you get it!! :)
I agree with wheresmydessert - when you send the pictures, just point out why you like it - the shape of the diamond, the setting, the metal, etc. You might mention to him that size doesn't matter as much as _______ (color, clarity, setting, whatever). Or if size is important (and it's okay if it is!) say you'd prefer it be bigger than he spend a lot of money on the setting or side stones or whatever.
When my husband was deployed, I sent him pictures of rings I liked and told him that he could find them in smaller or larger versions, depending on his budget. I didn't want to know his budget, but he actually told me he didn't have one and would just kind of wing it. I told him to spend what he felt comfortable spending
Often, I could just get a picture of the setting without any particular center stone in it!
Keep in mind, that since he's deployed, his income is all TAX FREE! So depending on his rank (E vs O anyways), he might be willing to spend a little more than you think.
The big Q is, do you prefer a bigger center stone or bigger setting? My setting is actually mroe carat weight than my center stone, but I love the different stone cuts and variety.
Go try some on and see what you like. Look at the price tag, and ask yourself if you think it's too much (since you probably know his salary) or if you're uncomfortable with it.
And, if he cant afford anything too big, it's ok to get the setting you want, with a smaller stone, and upgrade to something more substantial later if you want, say a 1.5 carat and he can't spend 15K on a ring.
ALSO, there are military px shops (not sure where) that sell diamonds FOR soldiers. I'm not sure if it's a px or what it is. The biggest they sell is typically 1 carat, but there's no tax on it and it's a damn good price. He may not be aware of that resource and you could get a good center stone ther,e then a setting later.
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Well hello again, lovelies!
My love is currently overseas (in Iraq until next month) and has asked me how I envision my Engagement Ring! So, after first trying to contain my squeals of excitement and joy, I realized that it is an awkward subject in that I immediately felt presumptuous. He, of course, insists that it is not being presumptuous and wants me to send him pictures of rings that I like. This presents another awkward situation because ring pictures usually show HUGE rocks and I don't want him to think that I expect him to buy some GI-NORMOUS diamond...how did you go about ring shopping without feeling demanding?
:) Miss B