I [name_u]LOVE[/name_u] [name_u]Sullivan[/name_u]! I feel like [name_u]Sullivan[/name_u] is classic, masculine, and comes with “[name_u]Sully[/name_u]” as a great nickname! I also think [name_u]Sullivan[/name_u] [name_m]Thomas[/name_m] has a great flow to it.
I like both [name_u]Sullivan[/name_u] [name_m]Thomas[/name_m] and [name_m]Rafferty[/name_m] [name_m]Thomas[/name_m]. Both have great flow and great nickname potential. I would [name_m]Dempsey[/name_m] [name_m]Thomas[/name_m] because the flow is awkward, there’s no good nicknames, and it sounds more like a last name than a surname-y first name.
I like [name_m]Rafferty[/name_m] and [name_u]Sullivan[/name_u]. [name_m]Dempsey[/name_m] reminds me of the actor and has no easy nicknames (though I now cannot unsee “dumpster”).
My favourite is [name_m]Rafferty[/name_m], although I really like [name_u]Sullivan[/name_u] as well. Great choices, I’d love to know your other boys’ names!