Olga and Vladimir met each other, but I think that might have only a few times. OTMA did meet his two sisters Irina and Natalia frequently on walks through the Alexander Palace and on Princess Paley's work shop, but before the war, Vladimir was frequently away at the Corp de Pages and after it he was fighting in it. But Princess Paley does mention one of these meetings in her memoirs in 1916:
We left Kiev on November 16th/29th for Mohileff, where the Grand Duke, with his suite, reinstalled himself in a house which he had rented at the moment of his being appointed Chief of the Corps de la Garde. I and my little daughters remained in the railway compartment which we continued to use as a residence. We remained in it a week. The Empress and her children had come to pay a visit to the Emperor. We were sent word that on November 22nd (old style) the Emperor, the Empress, the four Grand Duchesses and the Tsarevitch would come and drink tea with us at four o'clock. Great excitement! Our excellent chef began at once to prepare all kinds of sandwiches and cakes and petits fours, in which he excelled, and I and Vladimir set to work to find nice out-of-the-way sweets and fruits. An enormous table was laid, for we were to be a numerous party. At the hour fixed, the whole Imperial family arrived. The Emperor was rather pale and seemed tired, the Empress looked beautiful and smiling, with a great deal of colour in her face. The Tsarevitch, with his refined and charming countenance, struck me by his look of fragility. The thinness of his neck distracted me. One could have taken it with two fingers. The four young Princesses, a little shy, placed themselves at one end of the table with the Grand Duke Dimitri, son of the Grand Duke Paul by his first marriage with the Princess Alexander of Greece. As hostess, I was at the other end of the table, the cups and samovar in front of me, with the Empress on my right and the Emperor on my left. The Grand Duke sat on the other side of the Empress. The afternoon passed gaily. The Empress wanted to know what I thought of the Livadia Palace, and I found myself torn two ways between the wish to be truthful and the fear of offending her. The Emperor came to my rescue and said with a laugh:
"The Princess has at Tsarskoe the most beautiful house in the world, a veritable museum. How can you ask her to say what she thinks of our house, in which we have put more or less anyhow the things we liked, and which has no kind of style at all? "
Meanwhile the young people had retired to the drawing-room, and Vladimir, the life and soul of the company as always, had set some round games on foot. There was no feeling of constraint, no awkwardness. We could hear them laughing and shouting, and the dear little Tsarevitch seemed to be amusing himself enormously. His parents had all the difficulty in the world to get him away towards seven o'clock.