Bruce: him, why because you thought there where a million other women he would want, he confessed at a gala on the balcony overlooking Gotham after one of the men kept on asking to dance and talk with you and you both where able escape the man and woman that wanted you both. How simple "listen I know this is going to be weird and depending on your answer this can go in two different directions so I want to say that I have recently taken a more then friends interest in you and I see myself in a relationship with you but I don't want to put you in any sort of dan-" but he was interrupted.
Richard: both of you, you guys where in your hideout and how you may ask simple "I have something to say to you" you both had said at the same time you both laughed "okay rich I have an idea we both say it on the count of three...one....two....three" "I think of you as a girlfriend/boyfriend" you both looked at each other and laughed you talked to each other and agreed that the relationship must be in secret for a while.
Jason: him, you where at home building something for a new customer when you heard clashes and saw some scrap metal fall "I'm okay I did not die *this time*" "hahaha you the great jt fell over hm add that to the list" "hardie har har I just came to say I think I might be in love with you"...... "oh I..I also seem to have those feelings toward you"
Timothy: you, how simple you wrote it in his coffee foam at the corner cafe and books creative and cute and he wrote in your coffee foam when he saw it.
Damian: him, how you may ask simple he walked up to you in the morning before school and gave a single rose with a letter attached to it saying "I can feel it, maybe you can feel it too, I am crushing on you and I hope you like me too."
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Batboys preference
RandomI will be doing this maybe when I can and this does include Bruce no need to worry my fellow bats 🦇