I've got an Oscar and Dempsey tank as well...in a 55...started out with them both really small...about 3" for Oscar and probably 2" for Jack. (Love those creative names, huh? LOL) They will also hang around eachother but I wouldn't say I've ever seen them "cuddle", although they do seem to sometimes enjoy each others company. Sometimes. Other times they will charge at each other. It's pretty even though...they seem to take turns. Of course Oscar has grown soooooo much faster than Jack...probably better that way, as Jack is the "more aggressive" of the 2.
How long have you had them? How long till your 55 is cycled?