2 January 1969
Hey kids, ever wished you could see Dean Martin and Frank Sinatra playing kinda gay. Today, your vaguely articulated whim is my command.
This sketch starts off with the pair disappointed to discover they’ve been matched up together, gradually accepting their compatibility, dancing together and then the cops come to dance them off stage.
This sketch is more about the two enjoying themselves together in front of an appreciative audience, which is the whole rat pack thing. Indeed, part of the “fun” is their bewilderment - as the characters in the sketch, these two internationally famous womanisers (“what do you consider most important in a date”: “38-24-28”) and also as the performers of the sketch - wondering “what the hell are we doing in this?”
If these were proper (comedic) actors these performances would be a lot more thought out. Instead you get the occasional lispiness moment from Dean. Sinatra does become more effeminate towards the end, particularly his reply ”If you don’t know then it won’t make any difference” to Dean’s “Why aren’t you a girl”.
Notice that it takes the audience a moment or two pick up on Dean’s “I can’t think straight” gag. Note also the “three children – one of each” line.
Frank Sinatra appeared on The Dean Martin Show on 2 January 1969 and 31 December 1970. Since a quick search shows that a large number of sitcoms had plot gimmicks about computer dating and a few chat shows and news programmes featured discussion of computer dating in 1969, I suspect this means computer dating was a current topic and that this sketch is therefore from the 1969 show. And what could be more extreme computer cock up than the possibility of two men dating each other