D&D 5E Advice on building my first character

Hello everyone!

D&D noob here looking for some guidance from the experts in regards to bringing my envisioned character into the world of D&D.

What I envision is an assassin type character that becomes one with the shadows, using them to disappear and reappear in all corners of the battlefield. Using this to quickly strike at an enemy commander dealing a devastating blow with his twin sabers before using the shadows to disappear and reappear elsewhere, striking another unwary foe. Bringing chaos and disorder to the battlefield and dealing death to those who least expect it.

From my research I've been able to come up with a multi class approach that I think would satisfy my needs quite well, but as I am very new to this, I am sure that I could benefit from the input of those with more knowledge and experience.

My build is as follows:

Fighter 2 || In order to get twin weapon fighting as well as the action surge needed to move around the battlefield more efficiently in a moment of extreme need (or extra burst).

Rogue/Assassin 12 || The burst potential from sneak attack and assassinate seems like it's exactly what I want for that quick devastating blow on targets that don't expect it.

Monk/Way of the Shadow 6 || perfect fit for my thematic Shadow melt powers, not to mention it adds some great features like extra attack, ki powers to gain advantage/surprise, and extra ways to both disengage and move about the battlefield.

I would also spend 1 ASI on the dual wielder feat, as my DM has pre approved the use of feats as long as it is perfectly reasonable that our character's actions would lead him/her to attain them. This would enable me to use double rapier.

I'm not too concerned about my character doing the maximum possible damage or min maxing, but I do wish for him to be good at what he does as it fits with his theme. My priority is to make a character that fits my vision, while remaining (at least) relevant both in and out of battle.

I look forward to reading everyone's advice, suggestions, and comments.

PS: Hints on how to efficiently go about implementing my character's fighting style into an encounter would be GREATLY appreciated, as I am pretty overwhelmed by all the possibilities.

Thank you for reading.

I'd say you pretty much nailed it. There's a little conflict between using your bonus action for an offhand attack and using it for martial arts, but it's not a big problem.

About the only thing worth considering is a couple levels of warlock so you can see in magical darkness, but then you need to have a decent CHA score, you'll be beholden to some jerk patron... it's probably a multiclass too far.

Also worth considering the Mobility feat at some point. The monk's Step of the Wind does basically the same thing, but it costs you a ki point and your bonus action.

Consider dipping warlock 2 instead of fighter 2.

Action Surge is good, but Two weapon fighting not so much. Consider that rogue has extremely busy bonus action. The only reason to use the bonus action attack over cunning action is if you missed your sneak attack. A warlock 2 will give you devil's sight instead, which is the best darkvision in the game, since it allows you to see inside the Darkness spell that you get through Monk. You also get access to Scag cantrips and get back some of the sneak attack damage lost.

I'm also a fan of Caster 5/Rogue x specs to get haste/shield/invisibility/misty step/fog cloud. It lacks monk's mobility but it's a better rounded build.

See if your DM will let you use Scimitar for martial arts. No real reason not to (1d6 unarmed to 1d6 slashing) then you don't need fighter.

I like your vision. One thing to think about what level you start at. If your DM is starting at 1st level and going up from there you won't have all of that together from the beginning.

Rogue will give you stealth and a good amount of what seems to be your core concepts. Ranger might also fit some of your needs and/or replace some of your fighter needs like the fighting style. It also has Hunter's Mark where you do extra damage with every attack to a target you are hunting, which may meet your theme. But Fighter 2 is a great choice with lots of nifty abilities, can't gainsay it.

If you consider Monk part of the core of what you envision, you need to start soon to get up to Monk 6 in a reasonably time. But it may not be giving you the rest of your vision in the meantime.

Good luck and have fun!

famousringo said:

Also worth considering the Mobility feat at some point. The monk's Step of the Wind does basically the same thing, but it costs you a ki point and your bonus action.

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You are right, the mobility feat would be a great addition to the build. Definitely going to try and work it in there if possible.

Gtdef said:

Consider dipping warlock 2 instead of fighter 2.

Action Surge is good, but Two weapon fighting not so much. Consider that rogue has extremely busy bonus action. The only reason to use the bonus action attack over cunning action is if you missed your sneak attack.

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This actually makes a lot of sense. I still very much like the action surge simply from all the possible uses it brings to the table. Two Weapon Fighting does seem like a lot of investment for a bit of extra damage that I would rarely get. Might drop it for something else all together... Although aside from Archery (would be kool to be able to assassinate from afar if the situation demands it), none of the other fighting styles really fit into my character. Gonna give it some extra thought.

mellored said:

See if your DM will let you use Scimitar for martial arts. No real reason not to (1d6 unarmed to 1d6 slashing) then you don't need fighter.

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DM says technically it makes sense, but that would set a bad precedent for other players to start asking for thematic cosmetic changes. I can understand how that would lead down a slippery slope that could lead to players feeling cheated or think I get preferential treatment.

Blue said:

Ranger might also fit some of your needs and/or replace some of your fighter needs like the fighting style.
If you consider Monk part of the core of what you envision, you need to start soon to get up to Monk 6 in a reasonably time. But it may not be giving you the rest of your vision in the meantime.

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I originally looked at Ranger instead of Fighter, seemed a more natural choice. But the versatility of action surge has gained a lot of value to me.
I plan to progress as Rogue 3 > fighter 2 > Monk 6 > Rogue 12. I think this would lead towards a nice story of my character starting as a Spy or Criminal who slowly gets influenced by his friends through many adventures, but eventually is either unable to escape the life of an assassin or wishes to demonstrate how rogues can use their powers to protect those close to them (open to change according to campaign progression, but its an idea).

Regarding the Warlock lvl 2, I think this is the hardest choice I have to make. I was completely unaware that my character would not be able to see after using the Darkness spell, something I planned on using a lot. The extra damage from spells is also nice to have, but like I mentioned earlier, I keep getting more and more attached to the idea of action surging in emergencies. I can definitely see how necrotic damage can fit into the chaos assassin theme as well as the much needed vision. This is going to be a tough decision.

I think no matter what route I end up going, I will have a blast playing this character.

Thank you everyone for taking the time to help me out!

lXlXero said:

I plan to progress as Rogue 3 > fighter 2 > Monk 6 > Rogue 12.

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A word of caution. Increasing you ability scores (or taking a feat) is usually every 4 class levels. With what you have above you won't be getting one until character level 9 when you hit Monk 6. For your character, Dexterity helps chance to hit, damage, AC, reflex saves, initiative (important for assassin) and stealth checks. While rogue 4 doesn't give a sexy power, I'd strongly suggest taking it upfront. Then you'll get an increase at character level 4 and again at 10th, not too far behind those in a single class getting it at 4th and 8th.

Dex 20 and the duel wielder feat will take 3 advances assuming you start with a 16 or 17 Dex. This assumes your DM is using the standard array or point buy. If you are rolling then it's a much different story, and with so much focused on Dex for you all you need is one excellent roll.

Good catch!
Definitely will take Rogue up to 4 now before switching. Thank you Blue.

Edit-I didn't see Blues post before posting, sorry for repeating what he said.

I have a strong bias against multiclassing. But it sounds to me like going pure Shadow Monk will give you everything you want, and still make you a decent character. Unless you start off as monk, you will find yourself pretty weak at just about every lvl past 3. While other classes are getting a feat at lvl 4, you will get some pretty useless lvl 1 stuff from warlock or fighter, at lvl 5 when everyone is getting an extra attack or more ki points, or very powerful lvl 3 spells You will be getting a nice fluff ability, you won't get a feat or stat increase till lvl 9, and only 4 total through your career. You won't get an extra attack till lvl 10. There are certain lvls were single class build get very nice things. By doing this lvl of multiclassing you will miss out on alot.

I would strongly recommend as your first character, playing a single class and enjoying what it has to give.