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Eleven / Kathryn Janeway: Why? She's his type. Unlike many another version of the Doctor, he's good at endearing himself to competent authoritative women. Depending on when in their respective timelines this meeting occurs, he might also impress her by bringing his very own nurse (Rory) along, which given that Voyager is desperate enough for nurses to let their own Doctor draft Tom Paris will definitely be a plus.


Five / Benjamin Sisko: Why? Mutual bonding over argumentative companions and cricket vs baseball. Five would be charmed by the Ben and Jake father/son relationship (and depending on whether this is before or after Adric dies also melancholic), and wouldn't ruffle Sisko's feathers the way some other Doctors might.


Nine / Jean-Luc Picard: Why? Picard would respect Nine's chip on the shoulder and not wanting to talk about any personal issues (and vice versa). (Though Deanna Troi, sensing Nine's emotional state, wilil try to corner him, but that's another issue.) Depending on the situation they're in when they meet, there might be some prickliness at first, but I think generally they'd find it easy to ally against the menace of the day and maybe share clipped yet meaningful conversation over some tea and/or bond over Dickens once that's done before Nine takes off again.


Fifteen/ Michael Burnham : Why? Much of her personal arc is going from repressing it all stoicism to openly emotional behavior, accepting your past grief and guilt and continuing to do better (and helping others) in the present - that's what he's practically the embodiment of for the Doctor! They would work well as allies, and there would definitely be dancing at some point. Also, she'd make him promise to visit Zora now and then as he travels through time.


Three / Saru (who was a Starfleet Captain, too): Why? Three can come across as incredibly high handed on first impressions, but Saru is a masterful diplomat, would spot Three is actually knowledgable and competent beneath the bluster and would lintrigue him as a Kelpian so any initial problems would be quickly moved aside in favour of teaming up. 'They would also bond over Buddhism.


Thirteen/ James T. Kirk: Why? No, not because he'd hit on her. (TOS Kirk, not AOS Kirk, i.e. he's not his pop cultural stereotype.) She'd consider him fun to have an adventure with, he'd be curious and charmed and very amused once she inadvertendly outs Scotty's inflated time estimations, whereas with male versions of the Doctor he might feel initially one-upped.


Twelve/ Christopher Pike: Why? Even if it's early Twelve at his prickliest, Pike's general relaxedness and experienced diplomacy would help smoothing things over. Conversely, Twelve could empathize with the whole "knowing your eventual awful fate" part without insisting on talking about it the way some other Doctors might. I predict at least one meal cooked by Pike while Twelve plays guitar before the Doctor leaves again.


Unfortunately, I can't think of any version of the Doctor who'd get along really well with Captain Archer because Archer would, depending on the point of his timeline, suspect the Doctor of being a tool of the Vulcan High Command, the Admiralty or the Xindi, while the Doctor, any of them, might like Porthos but would find Archer incredibly annoying, and that's before they find out about certain episodes involving slavery or torture.


Therefore, you get a bonus pairing:

Seven/ Gabriel Lorca (no, not the one we never met, I do mean the season 1 of Discovery guy) : Why? Mutual mindgames! Who manipulates whom best? Who sets a trap for whom while pretending to be their harmless facade? Who figures out the truth about the the other guy first? Might there be conversations with increasingly disturbing subtext about mentoring young women with a chip on their shoulder and tremendous guilt and anger issues? One thing is sure: it would be incredibly entertaining.


The other days