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I plan to play a bard who is very seductive, somewhat of a Casanova. Do I roll persuasion, performance or some other skill check to determinate the outcome?

Our game is less dungeon-delving and more social situations, so I expect this to come up often enough. Usually our group just roleplays seduction attempts but this PC is very promiscuous and I don't feel like roleplaying it out every time my character tries to seduce an NPC. It would become awkward for me, the DM, and the rest of the group. So I'm looking for a rule I can fall back on.

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    \$\begingroup\$ What do you roll for seduction? The eyes of every other player at the table. -- "not again, do they have to sleep with every character we meet?" :-P \$\endgroup\$ – Lyndon White Jul 3 '17 at 6:25
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There is no set skill for seduction. It's going to fall back to a discussion between you and your DM on which ones you feel appropriate, with the DM having the final say.

Personally, I don't think it's actually tied to any one skill, it's going to be the overall nature of what you're trying to do.

  • Trying to seduce someone you have zero actual interest in, as a strategy point, a way to achieve a completely separate goal? Sounds like you don't actually have a (direct) interest in bedding him/her, so Deception.

  • Trying to seduce someone because they're beautiful and you just want in his/her pants on general principles? Persuasion

  • Oh, wait, you're using music, song, poetry, and other Performance type things as the core of your seductive effort?

  • And while I certainly hope you're never this gauche, this cruel, trying to convince someone that his/her only hope of survival is to partner with you sounds very much like an Intimidation effort to me.

It's also worth noting that a clever player or DM could come up with even more interesting, less obvious combinations. An NPC whose attracted to muscle men may take an athletics check; you may peel a lime in a single, long strip with sleight of hand to suggest your abilities in the bedroom; a creative player or DM could probalby find a way to be suggestive with a LOT of skill checks -- or even a flat out ability check.

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In the games I've played, when someone attempts to seduce an NPC, I've seen the DM call for either a Deception or a Persuasion check, depending on whether the seducer has ulterior motives which they're trying to conceal from the NPC. I've never seen anyone call for a Perform check, although you might be able to persuade your DM to use that skill if you narrate how you're specifically seducing someone using a song or dance.

In a comment you noted that you wanted to be the character that tries to seduce a dragon. You might like “D&D: The Thing With The Dragons”, which is a story about a D&D game where someone tried this...

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What you roll exactly is going to be usually a social skill check.

Which one will be a DM call, depending on what you are trying to do. But there are some non-magical "hard" mechanics you can use.

Ask the DM if you can use a skill feat from Unearthed Arcana called "Diplomat".

It grants +1 charisma, proficiency or double proficiency in persuasion, and the ability to charm someone who isn't in combat with you (or your allies) by talking to them for 1 minute and beating them in a skill contest (until they are more than a certain distance from you, and 1 minute longer).

Charming in 5e means they cannot attack you (yawn in a social context, but has some fun to it; a guard who you Charm cannot use violence to prevent you from doing something), and you gain advantage in further social skill checks.

Another good one is Empathic, where you can burn an action, make a check, then gain advantage on your next attack or check on the target. It gives you insight proficiency (or double proficiency if you already have it) and +1 charisma as well.

As written, these stack; the round before you make your Charm check, you can Empathic (Insight vs Deception), and if successful get advantage on the (Persuasion vs Insight) check. It even fits thematically.

Note that the Charmed condition is not the Charm spell. The person Charmed does not know they are under the condition; the spell, in comparison, informs the target.

This is a lot of work to apply the Charmed condition, especially because you must succeed at a skill check to apply it. But if the DM is likely to ask for more checks, or different social skills against different targets, it can help. And, as written, it cannot hurt.

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