Voyager, Season 6
I'm not saying that B'Elanna and Chakotay in Maquis digs is the best part of this episode, but that's only because Barclay also has a cat named Neelix.
This episode, about the continuing saga of Reginald Barclay's mental health, takes place almost entirely on Earth. Barclay is now working at the Pathfinder project, which has something to do with deploying a bitchin' sensor array and contacting Voyager. Something has gone terribly wrong, which leads him to summon Troi for a house call, thus beginning Marina Sirtis' career of enabling bizarre TNG episodes to happen on other Star Trek series. Girlfriend is looking good! She wears this expression for almost the entire episode:
I can't even be bothered to speak in Troi's accent for this one.
Not shockingly, Barclay's holodiction has returned, and this time his obsession of choice is a program of Voyager, where he plays the Most Valuable Crewmember and everybody's BFF. He even sleeps in holographic quarters, despite having the sweetest apartment ever shown on Star Trek. While a few dilithium crystals short of a warp core breach, Barclay is still a genius, and he comes up with a way to communicate with the actual starship Voyager. Owen Paris makes an appearance, the real Voyager crew toasts Barclay as an honorary crewmember, and Barclay gets an off-camera girlfriend. She isn't a hologram, so I don't foresee this working out long-term. More importantly, I found this on fuckyeahtng and it's brilliant:
Sometimes they take me days.
Programmed to her specifications.
The Voyager Society for Creative Anachronism strikes again, this time with a ye olde Irish town. Janeway falls for the holographic bartender and begins messing with his program to make him a better holographic boyfriend. All of this seems normal - the holodeck is for porn, after all - until she has a crisis about whether the hologram loves her back. The Doctor, ever a fan of holographic equality, encourages her to continue this relationship, just in time for a spatial anomaly something to destroy most of Fair Haven. Tom manages to save Michael's program. Janeway locks herself out of making future changes to his program so that it will be like a real relationship. Oh, Kathryn.
Because these things seem to happen a lot, the characters in Fair Haven start evolving and interpret the crew's use of holodeck controls as "dark magic." They react by capturing Tom, Harry and the Doctor and trying to exorcise them and/or burn them at the stake. Janeway doesn't want to shut down the holodeck, which would erase Fair Haven, while B'Elanna flips out and tells her that Michael can be reprogrammed, but Tom can't. (In modern-day terms, Janeway is rescuing her laptop with The Sims on it from a burning building while hoping her family can make it out of the fire on their own.) Janeway convinces Michael that they're not evil spirits at all, but time travelers from outer space, and everyone ends up happy except B'Elanna, who is starting to wish the holodeck had never been invented. I love her in this episode. She should play the voice of reason more often. While I think this episode casts some doubt on Janeway's remaining sanity, as well as highlighting the emergency need for some rules to be laid down about not creating sentient holograms willy-nilly, she and the holographic boyfriend are really pretty cute:
I forgive you the crack shenanigans for making Janeway smile!