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I think whatever looks good to you is completely fine. I don't know that "monogram" rules or etiquette even exist!
I'd say just go with what you think looks best - I don't think there are any specific rules - just do what you like!
Even if XdRy is the technically correct way, I think that would look sort of strange as a monogram.
DOn't know if this helps but I was looking at the link to the journal that you posted and it says that the max letters for personalization are 3 - so xDy would win!
Because a 3 initial monogram is standard, I think you need to pick either D or R and go with that.... XDY or XRY.
How does his last name typically get alphabetized? I'd think by "D", right?
@ssv - I chatted with the journal designers, and they said I could put whatever I wanted on there, so unfortunately there's no automatic WIN for me. Bummer.
@oracle - He likes to be alphabatized by the "D," but wants his whole shebang on the monogram. What a needy man. 
Thanks for all your input! I think that I'm going to pull the "I'm doing most of the planning, therefore I win" card here. Oh, and the "I'm putting it on my card, so I win" card. It's good to know that I've got reinforcement though!
I agree that XdRY would look awkward! Here's an idea though - could you use an intertwined D and R for the centre initial? That way it would still look balanced, and he gets his R. I did a quick mock-up using a Victorian two-initial monogram at the centre and I think it looks pretty good, although in your case maybe you'd prefer to switch the outline and fill so that the D would be emphasised more than the R.
xdry.jpg (9.6 KB, 41 downloads) 2 years old
Thanks studio! That looks fantastic, and I'm definitely keeping that idea around!
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Hi Bees!
Please help me resolve a disagreement with my other half! We're hoping to get this journal to use as a guestbook/photo album. It's expensive, but it's so freaking perfect for us! I've got some adorable colored pencils, and I was going to ask guests to draw a picture for us, and sign this book. We'll get a lot of stick figures, but I think it will end up pretty cute. Then we'll use the remaining pages for the best photos.
Aaaanyhow, this beauty comes with an engraving on the cover, and I want to put our monogram on there. I'm still debating the name change, but luckily our last names both start with "D," so I thought a monogram was still possible. His last name is Spanish, so it's along the lines of "de Ruiz." He insists that our monogram should be "XdRY" (with X & Y for our first names), and I'm thinking it can just as easily be "XDY."
Anyone out there with complicated monogram experience? I really want to prove him wrong, but I have a scary suspicion he's right. Dang it.