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I know that Halflings can hide behind people, that's their special thing. But could a Small sized character with Skulker hide behind a Normal sized party member and claim the partial concealment needed for a Stealth check? This feels cheesey.

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No

Being behind another creature does not allow you to hide.

The rules

To attempt to hide from a creature you must be not be seen by it (PHB p. 177). The Skulker feat allows you to try to hide when you are lightly obscured from the creature from which you are hiding (PHB p. 170).

A lightly obscured area is defined as such:

Vision and light (PHB p. 183)

In a lightly obscured area, such as dim light, patchy fog, or moderate foliage, creatures have disadvantage on Wisdom (Perception) checks that rely on sight.

Dim light, also called shadows, creates a lightly obscured area. An area of dim light is usually a boundary between a source of bright light, such as a torch, and surrounding darkness. The soft light of twilight and dawn also counts as dim light. A particularly brilliant full moon might bathe the land in dim light.

A character sitting behind another one (be it an enemy or a friend) - regardless of their relative size - benefits from half-cover (PHB p. 196). This does not affect the lighting conditions and visibility of the general area (unless the creature you are hiding behind is accompanied by a dreadful aura of darkness, but in that case you or your enemy probably have bigger problems on your hands).

The intent

Hiding behind other creatures was clearly meant to be "the thing" for halflings, so allowing it for any character would be taking away from their flavor.

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  • \$\begingroup\$ The only problem with this answer is the crowd situation. Children are easy to lose in a crowd because you can't see them. Small creatures should have the same benefit. \$\endgroup\$ – Escoce May 13 '16 at 15:55
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    \$\begingroup\$ @Escoce hiding in a crowd is a totally different situation than hiding behind one person. It's kind of like hiding in a forest vs holding a branch in front of your head and saying you're hidden. :) \$\endgroup\$ – Olorin May 13 '16 at 15:59
  • \$\begingroup\$ Agreed, but it is still possible to hide behind a single tree, or in this case a single humanoid. \$\endgroup\$ – Escoce May 13 '16 at 16:01
  • \$\begingroup\$ @Escoce It's pretty hard to gain total cover from a single, stand-alone tree, although definitely possible. The PHB gives narrow tree trunks as examples for half cover, and thick ones for three-quarters cover. RAW hiding would be allowed only in total cover. \$\endgroup\$ – Olorin May 13 '16 at 16:04
  • \$\begingroup\$ That's for a medium creature. \$\endgroup\$ – Escoce May 13 '16 at 16:05

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