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Yes, it is a wonderful and very romantic idea. "Men ~ take note. Very romantic idea. If you don't know if she has the dress you want her to wear, buy her one and make sure it's a stretchy fabric so that you have a better chance at getting her right size.
Couple idea: His & Her's cell phone backgrounds of their couple pictures split to see the significant other; when the phones are set next to each other it is the whole/entire/original picture - So Cute!
I would not say this is when boys become men. I would say none of these are bad ideas. I would also say, if this is really what you think separates men from boys, you need to learn what separates girls from women.