Simon, Seeker of Secrets — Bloodborne

Quest overview

Obtain Simon's Bowblade and the key that gives access to the real Brador.

• Own the expansion.
• Open the shortcut in the Nightmare chapel.

• The alternative Holy Moonlight Sword route can be missed: collect the weapon before advancing Simon's quest.
• Do not try to heal wounded Simon with the Choir Bell.

Accept his conversation about the nightmare

Hunter's Nightmare · corridor behind the chapel shortcut door

Before Ludwig to see his full progression

• Return through the corridor behind the chapel door that was initially locked.
• Speak to Simon and choose the answer expressing interest in the nightmare.

His quest has begun.

Optional step: receive the sword from Simon

Underground Corpse Pile · near Ludwig's head

After Ludwig, before advancing Simon's quest

• This variation requires speaking to Simon before the boss.
• Speak to Ludwig's head while wearing Church chest attire, answer no, then reload.
• Speak to Simon near the head to receive the Holy Moonlight Sword.

Holy Moonlight Sword obtained.

Answering yes makes Ludwig hand over the sword directly and skips this meeting. It does not fail the rest of Simon's quest.

Check the optional Research Hall meeting

Research Hall · near the entrance lamp

After receiving the sword from Simon

• If Simon gave you the sword, speak to him at the Research Hall lamp.
• If you obtained the sword another way, go directly to the Lighthouse Hut: no reward is lost at this step.

No additional item; the next destination is the Fishing Hamlet.

Finish his route in the hut

Fishing Hamlet · Lighthouse Hut

After Maria

• Enter the hut and look for Simon on the floor, immediately to the right of the entrance.
• Speak to him until you receive the Bowblade and the Underground Cell Inner Chamber Key.

Simon's Bowblade and Underground Cell Inner Chamber Key.

If he is dead or his quest was never started, the key appears on a body near the lamp.

Catch up if you never met Simon

Nightmare chapel, then Lighthouse Hut

Even after completing the expansion

• The wiki states that you can still speak to Simon at his initial location and choose the answer showing interest in nightmares.
• Then find him at his final destination to receive the Bowblade.

Missing the intermediate meetings does not necessarily lock out the Bowblade.