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Duke was honestly tired of his brothers asking if he had someone. It had naturally started with Dick, excited to take him under his wing and give him dating advice. It was sweet back then, and he was glad his older brother wanted to bond. Just not in that way.
Jason first asked the question in relation to finding out Tim had been secretly dating a civilian for three years. Duke just assured him that was one thing that Jason didn’t have to worry about from him.
Duke really felt he’d lost the battle when even prickly ‘romance is for the weak’ Damian had announced that he and Raven were getting serious. Maybe he was wrong and he just needed to find someone who was as suited to him as Raven was to Damian.
That nearly cost him his friendship with Danny when he found that Duke actually really didn’t like kissing, and hand holding was iffy.
So at 35 with half his brothers happily married, Tim dating again after finally getting over Bernard, and the family even accepting that Jason and Jazz are partners despite refusing traditional marriage, Duke was tired of everyone asking when he would find someone.