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The spiked chain was an exotic reach weapon in D&D 3.5, but is absent from D&D 5e. The use of such a weapon (probably) falls under using improvised weapons.

Is there such a way for a character to become proficient with a exotic/improvised weapon without pursuing proficiency with all improvised weapons?

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There's no option for that.

As far as I know, there's only Tavern Brawler that can give you proficiency with improvised weapons.

But it doesn't make sense to be improvised.

Improvised weapons are pretty much defined by having no proficiency bonus (tavern brawler aside), so there's no real distinction between using a weapon you're not proficient with and using a weapon-like improvised weapon such as a pitchfork 'trident'. So there doesn't seem to be much point to invoking the Improvised rule.

It could just be a re-skin.

The easiest way is to just treat a spiked chain as a variation of one of the standard weapons, in much the same way that the monk's Martial Arts section (PHB p.78) discusses treating nunchaku as a special kind of club and so on. Treating a spiked chain as mechanically identical to a whip, pike, or halberd would probably be the most direct solution.

The Kensei monk from Xanathar's Guide to Everything (p.34) might pick 'whip' as his kensei weapon, or with DM permission a monk could use the Dedicated Weapon optional feature from Tasha's Cauldron of Everything (p.48) to make 'whip' a monk weapon (provided they're proficient with it). Then they could simply describe the whip as a spiked chain/rope dart/etc. You might even describe how, as you level up, you're moving to heavier and more elaborate chain weapons, which are all just a 'whip' from the mechanical side, and are technically getting increased damage dice from your Martial Arts feature rather than from being more dangerous weapons.

However, I suspect what you really want is something like a whip that deals better damage without using the kensei's Martial Arts. Mixing finesse with reach and good damage would be a pretty powerful combination, especially for a Rogue, so you would certainly need some restrictions to balance it.

How could you handle actual Exotic proficiency?

Since the core rules only have 'simple' and 'martial' weapons and only a very limited number of ways to gain a proficiency, there are only a few ways to address something like an 'exotic' weapon.

The Weapon Master feat would certainly make sense in this case; or you could home-brew a feat that gives you proficiency with one 'exotic' weapon and some other side bonuses. Probably the best way would be to think of the feat as adding damage with a specific kind of weapon -- in this case, the proficiency would be a lot like a feat that says "when you hit with a whip attack, you deal +2 damage" or some such thing (if the Spiked Chain were a d8 reach finesse weapon, for example).

But there are problems with that.

It might be worth-while for an "exotic proficiency" feat to require you already be proficient with all simple and martial weapons as a prerequisite, since otherwise exotic weapons immediately become the go-to choice for a character who isn't already omni-proficient and wants to pick up a better weapon. (That is to say, a paladin is already proficient with everything, so a feat that lets him pick a slightly superior version of one of those weapons represents 1 step up, while a wizard or cleric who acquires an exotic weapon proficiency is jumping up 2 steps.)

But that doesn't fix everything. There are ways to get around the proficiency system -- the warlock's pact blade, in particular, makes him always proficient regardless of form, so all blade-pact warlocks immediately find exotic weapons very attractive. Since the game doesn't have exotic weapons as a standard element, the rules won't contemplate them, and you have to be ready for unusual rules interactions. You'll need buy-in from everyone at the table, and an understanding that the DM can nix any weird combo effects that might show up.

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    \$\begingroup\$ Reskinning means finding the mechanics that best fit the intended goal, not flavor text. What would make a flail a more reasonable spiked chain substitute than, say, a maul or war pick? The superficial resemblance, in that a flail theoretically has a chain component, in no way makes it a good reskin candidate. In this case, the OP specifically referenced reach as a desirable characteristic, so all my examples were reach weapons. \$\endgroup\$ Sep 20 '18 at 17:39
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This wouldn't be an improvised weapon. Instead, this would be a weapon for the DM to homebrew based on existing weapons, per the usual D&D 5e guidance on extending the selection of available weapons.

Then it would be a matter of gaining proficiency with it as normal.

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In my campaign I have the spiked chain as 2d4, finesse, reach, martial so the only way to dual wield is to take the feat and then you still dont get ability score bonus to damage for the second strike. For balancing purposes you have to be proficient in martial and simple.

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  • \$\begingroup\$ So it's not overpowered and balanced out by not being light so you can't dual wield normally and you have to instead take a feat mine is also a chain whip so this might not help you but I wanted to put it out there. \$\endgroup\$ Aug 6 '19 at 17:43
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    \$\begingroup\$ Out of curiosity, why would anyone ever pick the whip or any other d6 or even d8 damage weapon if this was an option? You get reach, finesse, and 2d4. \$\endgroup\$
    – NautArch
    Aug 6 '19 at 17:55
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    \$\begingroup\$ Is there any class in D&D 5e that is proficient in Martial Weapons but is not proficient in Simple weapons? Your last sentence seems to be not necessary unless you can identify one. The "finesse" strikes me as one feature too many unless you reduce the damage, but I don't have the chart in front of me that David Coffron made a while back that explained D&D 5e weapons feature and damage progressions. \$\endgroup\$ Aug 6 '19 at 17:57
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    \$\begingroup\$ Also, Welcome to RPG.SE! Take the tour if you haven't already, and check out the help center or ask us here in the comments (use @ to ping someone) if you need more guidance. Good Luck and Happy Gaming! \$\endgroup\$
    – Someone_Evil
    Aug 6 '19 at 18:15
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Xanathars extraordinary vault has the spiked chain, it is finesse, reach and heavy, but when used by someone with the two weapon fighting style or feat it can be used as a double weapon no reach and counts as light

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    \$\begingroup\$ Hello and welcome! If you have time you can take the tour to find out more about the site. I assume you mean this Xanathar's extraordinary vault. This is not official content (which is fine!) but you should probably note this caveat in your answer. It would also be useful to share how playing with this option has turned out. \$\endgroup\$
    – Sdjz
    Jun 20 '18 at 16:27
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    \$\begingroup\$ That weapon in published material is a monster weapon, just as a giant's axe is a monster weapon. Discussion here might be useful \$\endgroup\$ Jun 20 '18 at 16:27
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This doesn’t have to be complicated. Ask your DM, write it into your back story, and use the old rules. The point of 5e is to be simple and incomplete. This is done so that players and DMs can have space to create and use their imagination to fill in the gaps.

As a DM I may require the player to exchange a proficiency in some other weapons or have a really great back story for using a spiked chain, but that's exactly what I want from my players.

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    \$\begingroup\$ It’s considered impolite to criticise other answers/people when posting an answer, and is likely to result in a negative score regardless of the merit of your actual answer. I’ve removed that part, so this has a chance to be rated on its other merits. \$\endgroup\$ Nov 26 '18 at 17:11
  • \$\begingroup\$ Relatedly, I will suggest the tour might be helpful to get oriented around here. Being a Q&A site, it works differently from a discussion forum, and the purpose of posts is very different. \$\endgroup\$ Nov 26 '18 at 17:14
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Take tavern brawler, and use a chain. Damage resembles a whip with a bonus action to grapple from the feat

An actual 5e spiked chain is used by the shadakar - shadow dance

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  • \$\begingroup\$ This is already covered in Darth Pseudonym's answer. \$\endgroup\$ Dec 20 '20 at 5:36
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    \$\begingroup\$ I think this answer could benefit (and stand out more) from expanding on the information available on shadakar/shadow dance. \$\endgroup\$
    – Ifusaso
    Dec 20 '20 at 6:49

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