Making a one shot shadow monk

[Foxydono]

As the title says, I'm making a shadow monk character at 12th level for a one shot. Not sure about stats, I'm assuming point buy, but that's not really important to me. As for books: all official material is allowed and UA is ask the DM area.

I would like to play a ghostwise halfling. I like the flavor and I have never payed a halfling before, so I'm thinking it will be fun.

Now I need some advice concerning multiclassing. Rogue is an obvious choice. At least one level for expertise, perhaps two levels for cunning action, three for either assassin/swashbuckler/arcane trickster or four for an extra feat and perhaps five for uncanny dodge?!

The second multiclass I'm considering is the warlock. Because a shadow monk without darkvision is like a rogue without sneak attack. It just feels wrong. But getting two warlock levels is a steep price to pay.

What kind of shadow monk would you make and why?

[pdegan2814]

I recently played in a One Short where I was a Shadow Monk, though we were at 16th level. I went Wood Elf and pure Monk and had a blast. I'd think carefully about multiclassing, Way Of The Shadow's 11th level ability is SWEET. Yes, it's not nearly as useful an ability if you're going to be in bright light most of the time, but if that's the case then a Shadow Monk is going to be pretty nerfed overall.

[Nidgit]

What do you need expertise for? If you're not specifically making a skill monkey, a one level dip in Shadow Sorcerer is the easiest way to get darkvision while focusing on Monk. The Rogue options you listed are nice but not really that necessary to a Monk.

Monk 9/Hexblade 3 would be pretty nice. The CHA attack stat feature is fairly irrelevant but Hexblade's Curse meshes pretty well with Monk attacks. Advantage, expanded crit range, and +4 damage per hit that recharges on short rest just like your ki looks pretty nice when you're frequently getting four attacks per turn. There aren't that many other first level Warlock abilities that fit a Ghostwise monk that well.

[LordNibbler]

No need for 2 levels of rogue. You’ll be using Shadow Step instead of Cunning Action. One level of rogue is useful if you want Expertise in Stealth and something else. You’ll have to use a short sword if you want a monk weapon that can also get sneak attack damage.

[Foxydono]

What do you need expertise for?
Expertise in stealth, but I could just take the feat stealthy. This would make more sense.



Monk 9/Hexblade 3 would be pretty nice. The CHA attack stat feature is fairly irrelevant but Hexblade's Curse meshes pretty well with Monk attacks
Why not dip only one level? You get the curse and that's the most important thing right? Or second level for devils sight, but as you mentioned earlier you might as well go one level in shadow sorcerer. This gives you some other benefits too.

[Foxydono]

No need for 2 levels of rogue. You’ll be using Shadow Step instead of Cunning Action. One level of rogue is useful if you want Expertise in Stealth and something else. You’ll have to use a short sword if you want a monk weapon that can also get sneak attack damage.
Yea you are right and if I really want stealth expertise I can take a feat for that. Guess I'll be skipping rogue then, especially if I need to use a short sword.

[Nidgit]

Why not dip only one level? You get the curse and that's the most important thing right? Or second level for devils sight, but as you mentioned earlier you might as well go one level in shadow sorcerer. This gives you some other benefits too.
2nd Level spells and a Pact Boon are stronger imo than immunity to poison/disease, +5 extra movement, and 1 more ki. But anything between 8/4 and 10/2 could work without much difficulty.

[CTurbo]

Gloom Stalker Ranger 3/Shadow Monk 9

Gloom Stalker gets you the very good Natural Explorer feature, a Fighting Style, Favored Enemy, Darkvision, an extra first round attack and movement.

Natural Explorer lets you ignore difficult terrain, have advantage on all initiative rolls, and advantage on attacks again enemies that have not acted yet.
Archery or Dueling fighting style would be great
Favorered enemy adds +2 to one enemy type(Humanoids IMO) to every attack you make and you will make a lot of attacks.
Underdark scout lets you hide better against other enemies with darkvision and your darkvision will be better than most.
You also know the Disguise Self spell.

[Foxydono]

Gloom Stalker Ranger 3/Shadow Monk 9

Gloom Stalker gets you the very good Natural Explorer feature, a Fighting Style, Favored Enemy, Darkvision, an extra first round attack and movement.

Natural Explorer lets you ignore difficult terrain, have advantage on all initiative rolls, and advantage on attacks again enemies that have not acted yet.
Archery or Dueling fighting style would be great
Favorered enemy adds +2 to one enemy type(Humanoids IMO) to every attack you make and you will make a lot of attacks.
Underdark scout lets you hide better against other enemies with darkvision and your darkvision will be better than most.
You also know the Disguise Self spell.
I did not consider multiclassing ranger, but you make a good argument. Damage wise you'll do aan excellent job and you get darkvision! I will probably give this build a try :)

[GorogIrongut]

Of the two possibilities, I enjoy:
-Gloomstalker. It's got loads of synergy with monk and can make your character much more robust with more options in combat.
-Arcane Trickster. This brings a lot of goodies to the table. Sneak attack. Extra mobility. Use of magic (booming blade and loads of ritual spells that provide out of combat utility). Uncanny Dodge. Extra attack.

If it were me, I'd do an even split, Shadow Monk 6/Arcane Trickster 6. You have to go Shadow Monk 6 for the at will shadow teleport. This also nets you the extra attack and stunning strike. If this were a character for more than a one shot, then I'd put the remaining levels into Arcane Trickster.

This is however a One Shot, so I'd probably recommend Shadow Monk 7/Arcane Trickster 5. This is because Evasion is more important than a second round of Expertise. It will also net you more ki points to use stunning strike on (without significantly hampering your access to magic).