I'm relatively new to D&D and I'm rolling my second character. While I enjoyed my first one, he didn't have much of a personality.

This next time around, I'm aiming to play a Swashbuckler named Montoya Daefaren. By peculiar luck (and the DM's blessing), he was made immortal due to the Tomb of Annihilation death curse. He'll tag along to quietly sabotage the party's effort to break the curse, at least until the DM decides to reveal his lady love has a wasting disease and will die forever unless he breaks the curse. He'll also be comic relief, as he's an alcoholic (with penalties if he doesn't drink or over drinks) and is capped at 1 hit die regardless of level. I imagine his mouth and party antics will get him killed several times per day.

The challenge is, I don't fancy myself much of a role-player. I'm struggling with how to play this spicy spaniard / Captain Jack hybrid.

I'm looking for tips from veterans to help get into the role, as it sounds like a lot of fun.


1 Answer 1


One thing I try to do is ask myself what my character wants. That way whatever situation he finds himself in, I have an easier time putting myself in the character's shoes. I'm talking here not about short-term goals, but much larger motivations.

For example, ex-Stormtrooper Gunnar Sykes didn't believe in grand abstract political visions of the Empire or the Rebellion. He just wanted to belong, to know he was with people who had his back. And he wanted adventure. He wanted to test himself and to never live a boring life. So he was extremely reliable in helping his friends, he was always eager to jump into danger, and he worked hard to improve his skills as a Hired Gun. He cared far less about proving anything to anyone but his friends, so he wasn't flashy, he didn't crack wise, and he didn't tend to talk all that much.

Montoya Daefaren has a lady love, so perhaps finding a soul mate is important to him. Or perhaps being in love, which is not quite the same thing, is important to him. Where does his alcoholism come from? Perhaps because he just can't handle being killed over and over again, and drinks to avoid thinking about the trauma. Maybe that's also why he is such a jokester – it's a way of avoiding this pain of constant death and resurrection (I assume that's how it works). Maybe he also drinks because he knows he'll outlive his lady love, and that knowledge wounds his soul.

So how do you apply this in actual play? Montoya wants to love and be loved. He wants to avoid the pain of the cycle of death and resurrection that is both blessing and curse. When he jokes with the rest of the party and they wind up getting pissed off at him, they don't realize that he just wants to be one of them, to be loved in a way, but he is so tortured by his situation that it comes out in this perverse way that winds up getting him skewered more often than he'd like.

That's obviously a tragicomic way of interpreting the character, but there are plenty of other ways you could play him, depending on what you determine his core motivations might be. You don't have to come up with all the picayune details of his personality, as you want to leave some room for that to manifest in actual play. But once you have a lock on his motivations, the rest gets easier.

  • \$\begingroup\$ This is great advice Erik! Especially the point about "why is he an alcoholic". I had to patch up his backstory to cover that. Montoya is driven to "win" his lady love. He and his family were indentured servants to her father, but she was married off to an elvish prince before sparks could ignite. He escaped his servitude to become a corsair, get rich, and wisk her away after a glorious duel. (As he imagines it playing out) So he's all about the money. He amassed a small fortune at sea, but lost it all after being a betrayal by the crew. Now he's broke and nursing his defeat. \$\endgroup\$
    – Anthony
    Commented Dec 4, 2017 at 2:50

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