Beautiful Anastasia, Happy holidays to you too,
Do not be offended. Just my terse opinion.
If we will imagine possible pair of Dmitry and Olga (in theory), we will see a lot of big problems in the future. I don't want to write here an endless serious article. Just the main things.
They are very different people. Modern, handsome, liberal, well-educated young man and good, orthodox, 19th century-minded simple girl. I also think that Dmitry was too smart for Olga. Moreover he, on my opinion, was on of the most smartest of the Romanovs of his generation. He always being aware of all the troubles which took place in Russia that time. Sober-minded liberal man, unlike orthodox Grand Duchesses. I think also that Dmitry Pavlovich always have been in a more serious circle of acquaintances and friends. Yusupov not in this account;).
So I cannot imagine this pair, both in theory and in practice.
Ally, by the way, I don't think that to be homosexual is a bad reputation. It's your personal choice and we shouldn't criticize it. We are not in 19th century. Otherwise we will have to condemn a huge amount of the Romanov Dukes, Grand Dukes, and other family members, who, with a different degree, were a typical "specific men". I don't want to name them. You know whom I mean;). Of course all of the Grand Duchesses were typical orthodox and conservative in their views, that's why they couldn't understand other things then typical family: mother, father and children. Nothing more.