TRULY I'm very glad you see the horrifying potential of this post as well
okay just imagine. they've been back on earth for a couple of months, no one in this group of people knows what the future holds exactly for them (two ex-maquis, one ex-maquis AND ex-con, one ex-borg), tom and b'elanna are exhausted since they're looking after a newborn baby. b'elanna is very pissed at chakotay for this relationship with seven thing (per this other post), chakotay resents that hostility and he's now mad at her and tom (whom he never liked, very understandably so because in addition to tom being kind of a dick to chakotay for no reason i don't think he ever truly forgot about janeway and tom making a fool of him with tom's fake defection, and now janeway isn't their captain anymore, so). tom in turn knows that chakotay doesn't like him and i don't think he'd lose an opportunity to get one up on him. then there's seven and b'elanna's whole rivalry (need i say more?)
to make a long story short probably the two people who are able to tolerate one another the most in that situation are tom and seven, and tbh i can see tom coming up with this whole double date thing and getting seven on board with the idea of "maybe we can make b'elanna and chakotay get along again". (except of course in addition to the more 'noble' motivation they both definitely have a score to settle)
but neither tom and seven are very good at banter in unfamiliar situations, i feel; i mean, at least tom can crack a joke (chakotay would not laugh) but seven would straight up just try a list of conversation starters, which would make b'elanna roll her eyes so hard. tom would start reminiscing about voyager and it'd inevitably be anecdotes involving him and harry, which after a while i think would make b'elanna upset because once again he's not including her. chakotay would respond with his own memories of tom's being insubordinate or some shit, which would make tom temporarily shut up but make b'elanna even more upset. seven might mention something mildly horrifying like she and icheb finding sleep on a bed uncomfortable compared to their old alcoves but finding the privacy of actual quarters refreshing, which would make chakotay and tom cringe but b'elanna would retort that it must be nice to get any sleep at all. if the topic moves to what starfleet plans to do with their requests of joining it will get immediately more awkward (since we know chakotay and tom got recommissioned and seven was shut out, b'elanna still a question mark). i can definitely see the night ending with a dessert half-eaten and a tom making a half-drunk allusion at his and b'elanna's nonexistent sexual life (see: newborn baby), and seven trying to make a joke about her sex life having gotten more interesting recently but really NOT nailing the tone. everyone goes home kind of scarred by the experience and in utter silence.
tl;dr i don't think a second double-date would happen