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Can a lightfoot halfling hide while in the space of some creature (like a Medium-sized or larger ally), and be hidden from an adjacent creature?

The halfling is not trying to hide from the creature with which it is sharing a space.

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    \$\begingroup\$ Related, in a way: "Can you do anything after moving into an occupied space?" \$\endgroup\$ – Medix2 Nov 4 '20 at 21:59
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    \$\begingroup\$ Hello Gary, welcome to rpg.se! Your question is a good question and has received a good answer, so some of us have voted to undelete. For more details, see the help section on deleting questions. In particular, it says: "If your question has good answers, though, it's not fair to have those answers removed along with your question: other users put effort into helping you and even if you no longer want the answers, somebody else might." \$\endgroup\$ – Thomas Markov Nov 4 '20 at 22:07
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You can't willingly end your move in another creature's space

While there are ways to unwillingly do this, there is no method within the rules to willingly end your turn in another creature's space. From the "Moving Around Other Creatures" section of the rules (PH p. 191 / Basic Rules p. 74):

Whether a creature is a friend or an enemy, you can’t willingly end your move in its space.

But what if I end up there unwillingly?

At that point, it's up to the DM to determine if you can hide there. If you ended up there unwillingly, your movement was likely seen, so a DM may not allow a creature to suddenly have no idea where you would have gone.

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  • \$\begingroup\$ The Hide action doesn't end your turn. A lightfoot halfling rogue could move into another creature's space, Hide as a bonus action, Attack with advantage => sneak attack (if their hide beat the perception of the target and the DM allows it), then move out before the end of their turn. So your answer is a useful reminder, but only the last sentence answers the question (which doesn't mention anything about ending your turn). \$\endgroup\$ – Peter Cordes Nov 5 '20 at 6:26
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    \$\begingroup\$ @PeterCordes: The rule isn't about where you end your turn; it talks about ending your move in a creature's space. You can't willingly end your movement - any part of it - in another creature's space.. So you can't choose to stop in another creature's space to hide, attack, drink a potion, or do anything else. See the linked Q&As: Move into nonhostile space attack and move, Can you do anything after moving into an occupied space? \$\endgroup\$ – V2Blast Nov 5 '20 at 7:33
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    \$\begingroup\$ @V2Blast: Thanks, didn't realize ending a segment of your movement (with movement remaining) counted as "end your move", but that does make sense that you can't actually do anything except continue past someone. The heading on this answer unfortunately says "end your turn". \$\endgroup\$ – Peter Cordes Nov 5 '20 at 7:35
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    \$\begingroup\$ @PeterCordes Sorry about that! I did mean to say move to match the quote. \$\endgroup\$ – NautArch Nov 5 '20 at 13:52
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Only if lightly obscured

Lightfoot Halflings have the racial trait Naturally Stealthy, whose description states (PHB, 28):

You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you.

This does not make any reference to being in another creature's space.

If the character is lightly obscured by a creature one size larger than them (generally size Medium or larger), then Naturally Stealthy allows them to attempt to hide. Otherwise, they must meet the regular standards for hiding - namely, DM say-so and not being clearly visible.

There is nothing to suggest that being in another creature's space affects a halfling's ability to hide.

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