D&D 5E Help me figure out when to take a 2-level warlock dip on my lore bard

Hey, thanks for reading. I'm fleshing out a halfling lore bard for what I hope will be a long-running campaign. The world itself is entirely homebrew, with some significant changes to things like languages, pantheons, racial origins, etc. from the PHB. Mechanically, though, we're going straight RAW except possibly adding crit success/crit fails (within reason - none of those goofy charts or 6 INT barbarians somehow acing an arcana check).

Anyway, party composition is as follows:
- Human sword/hand crossbow ranger (not sure which conclave he'll go for)
- Human vengeance paladin
- Human eldritch knight
- Tiefling hexblade warlock/rogue
- My lightfoot halfling lore bard
- One unknown PC to be introduced later (we're working on the world as a group and plan to rotate who sits in the DM chair with every story arc, with the other players controlling the current DM's PC while he/she runs the game. The first DM up is planning on holding off on introducing his PC until after he's finished his turn in the DM chair)

The paladin player might not be around until a few months from now, and potentially might not play at all depending on life circumstance. So this leaves my bard as the only full caster, probably main healer, skill monkey (the tiefling is starting warlock and taking a rogue dip later, so lots of skills will be on me), friendly party face, etc. We've got lots of damage output potential already, so I'm focusing mainly on support/control and healing spells.

Stats: 8 STR, 15 DEX, 15 CON, 12 INT, 12 WIS, 17 CHA (yep, we roll for stats, and all generally have pretty high stats - let's not get into that debate!)

Here's my expected spell progression, if I just keep with bard:
1: Minor Illusion, Vicious Mockery, Comprehend Languages (I think this will be vital since we'll have a lot of homebrew languages. Good to cast as a ritual before entering new towns), Dissonant Whispers, Faerie Fire, Healing Word
2: Cure Wounds (might replace this with something like Dispel Magic, Greater Restoration, or Major Image later on)
3: Suggestion
4: Shatter, Light (only one of us has darkvision, and I get the feeling we'll be in the dark a lot in this campaign...), ASI = CHA, DEX
5: Hypnotic Pattern
6: Leomund's Tiny Hut, Additional Magical Secrets = Counterspell, and depending on what that mystery PC is, probably either Revivify or Fireball, or possibly Aura of Vitality (though I feel like my concentration is probably best used on other things...)
7: Polymorph
8: Dimension Door, ASI = 2 CHA
9: Not sure...Raise Dead? Modify Memory?
10: Magical Secrets: Banishment, Fireball (if I don't already have it, Wall of Force if I do), Replace Shatter with Mass Cure Wounds, Prestidigitation
11: Mass Suggestion
12: ASI = Resilient (con saves)
13: Forcecage
14: Magical Secrets: Plane Shift, Chain Lightning or Disintegrate
15: Power Word Stun
16: Feeblemind (ASI = Warcaster)
17: True Polymorph
18: Magical Secrets: Wish, Gate

I don't really need another ASI/feat at 19, and the bard capstone is rather...unimpressive, so I'm leaning toward two levels of Warlock. I think having the extra low-level slots with short rest recharges will be super nice for extra healing words, plus I'd probably grab Eldritch Blast and Friends for cantrips. Friends has limited uses but seems strong in those few cases, and I think having Eldritch Blast will be a boon once we're dealing with lots of enemies with multiattack and Vicious Mockery loses its potency. For invocations, I'm thinking The Devil's Sight, since I'll likely be the party scout (the ranger isn't going for stealthiness) along with the rogue in a dark campaign setting with no darkvision. I'd probably also pick up Mask of Many Faces (tempted by Agonizing Blast of course...). Probably GOO for patron, possibly The Raven Queen. I could grab some spells off the warlock list that I already know, and replace my Bard choices with other useful things.

So the question is...when do I take this dip? It'd be nice to work through the above progression without delay and switch to warlock at 19, but that's ages from now and the basic utility stuff that the warlock dip could bring would make that a long, long wait. I'd go earlier, but I really want short rest bard dice and the level 6 magical secrets seem clutch for the party. Level 7 seems alright, but I'd be putting off that final CHA ASI. Level 9 seems like a pretty good place, but again that seems a long way off.

Thoughts?

Wait until at least bard 5. For short rest cutting words. Viscious mockery can work well enough for then.

More likely bard 9, when 2 levels will land you at level 11, and the third eldrich blast.

Though keep in mind, the more spells you have, the less cantrip you cast.

Hi,

You might find, especially with the utter lack of real spellcasting in your party, that staying with Lore Bard all the way is a big win.

3rd level spells at level 5, magic secrets at level 6, then 4th level spells, mass suggestion at level 11... the goodness never stops all the way until level 18, when you grab Wish.

Your party already has damage covered; your character is their only hope of getting high level spells on time, when they are most valuable. But only if you stay the course.

So... take Warlock at level 21?

Anyway,

Ken

Taking warlock mid game is never easy. Our Bard wanted to dip for a few levels now but he didn't respond to offers from possible patrons until now.

Ovarwa said:

Hi,

You might find, especially with the utter lack of real spellcasting in your party, that staying with Lore Bard all the way is a big win.

3rd level spells at level 5, magic secrets at level 6, then 4th level spells, mass suggestion at level 11... the goodness never stops all the way until level 18, when you grab Wish.

Your party already has damage covered; your character is their only hope of getting high level spells on time, when they are most valuable. But only if you stay the course.

So... take Warlock at level 21?

Anyway,

Ken

Click to expand...

The above. Also, don't worry about damaging spells, with your group you could go the whole game without doing one point of damage and be fine. Just take spells to give them advantage as your group has massive crit potential and get them out of tough spots. You will do damage with spells like Dissonant Whispers, which should provoke 2-3 OPP ATT with all kinds of riders tacked on with your group.

As the only healer in your group you might consider a life cleric dip, you get armor and a host of other good benefits, the main one being bless and the healing bonus of 2+spell level; that mean Aura of Vitality now does 2d6+5 for ten rounds, or 70-170 Hp of healing. Its a good enough spell to use outside of combat also.

You should take that warlock dip when it seems to make sense within the story.

Well sure, I'd find some way for it to make sense RP-wise. I really don't like level dipping when it doesn't really make any narrative sense to do so.

As I said there is one more player of an undecided class - right now he's thinking some sort of cleric, possibly the Grave Domain UA cleric. Either way we've got so many martial people that he's leaning toward some sort of full caster, so it won't be only me. I still plan on at least off-healing. As for damage spells, I'm not really focusing on those at all, but I've found in previous play that having absolutely zero AoE damage can sometimes be problematic. Easier to wipe out a big group of grunts with a fireball than to throw Faerie Fire or something and, after your martial classes have mopped up, look at their lost hitpoints from the few hits they took and thought things could've gone better. Anyway, I'll be picking Magical Secrets spells depending on whatever class that last guy decides to roll (though I think Counterspell is a given considering how universally useful it is, plus getting to add Jack of All Trades to it is just sweet). I plan on mainly dropping a concentration spell like Faerie Fire or Hypnotic Pattern for most fights, using bonus actions to Healing Word and actions to Viciously Mock things (or Dissonant Whispers when appropriate), and mostly spending bard dice on Cutting Words, but having a little extra firepower from Eldritch Blast could be really useful when our martial guys can't get close. Plus, like I said, short rest recharging Healing Words and utility invocations seems really, really helpful.

Decisions, decisions. Thanks for your input so far!

Update: I'm now level six, and am leaning heavily toward a one level dip in Shadow Sorcerer instead of the GoO Warlock at level 7. It still fits well with the RP that has gone on in my character's dreams. Basically, instead of picking up EB, Friends, 2 pact magic slots, three first level warlock spells (that sadly overlap a lot with bard stuff anyway), Mask of Many Faces (which would be hard to work with as a halfling, I think) and Devil's Sight, I'd be getting: 120' darkvision, Strength of the Grave to hopefully stave off death, Firebolt, Friends, Control Flames (for sneaking about), Message, Shield and Absorb Elements, all while maintaining a full caster slot progression. Seems like the better deal to me. Plus I could get one more feat this way (probably Bountiful Luck).