Great event! Since if you can get it to go off, you will fuel more riddles to come! I’m sure that was the intention, and you got it right on the money.

I’d make the drawback: "No other riddles may be played until the regroup phase." It would be more of a boon than a bane to have the current drawback, especally with enduring Shelobs.

Three Guessesses
Event • Response
If a riddle is about to be resolved, spot Gollum to add or subtract 1 from a named number. This can change the effects of that riddle.
’Not fair! not fair!’ he hissed. ’It isn’t fair, my precious, is it, to ask us what its got in its nasty little pocketses.’
H1 C 143
cool should be worded from the number you named in that riddle.

Two Guesses At Once
Event • Response
If you must name a number, exert Gollum to name 2. If either is correct, the appropriate results trigger as usual.
He hissed and spluttered... and wriggled and squirmed; but still he did not dare to waste his last guess.
H1 U 144
sure

Black Shadow
Event • Shadow
Play Gollum from your draw deck or discard pile to take a into hand a maneuver event from your discard pile.
No one would see him, no one would notice him, till he had his fingers on their throat.
H1 R 127
cool

Not A Riddle (2)
Event • Response
If a riddle is played, spot Gollum to choose one: shuffle your draw deck; count the number of cards in your hand, place your hand beneath your draw deck and draw the same number of cards; or play a maneuver event from hand (suspending the current riddle until the event is resolved). This can change the effects of that riddle.
’It must give us three guessesses, my precious, three guessesses.’
H1 C 135
l

Three Guessesses
Event • Response
If a riddle is about to be resolved, spot Gollum to add or subtract 1 from a named number. This can change the effects of that riddle.
’Not fair! not fair!’ he hissed. ’It isn’t fair, my precious, is it, to ask us what its got in its nasty little pocketses.’
H1 C 143

Two Guesses At Once
Event • Response
If you must name a number, exert Gollum to name 2. If either is correct, the appropriate results trigger as usual.
He hissed and spluttered... and wriggled and squirmed; but still he did not dare to waste his last guess.
H1 U 144

Black Shadow
Event • Shadow
Play Gollum from your draw deck or discard pile to take a into hand a maneuver event from your discard pile.
No one would see him, no one would notice him, till he had his fingers on their throat.
H1 R 127

Not A Riddle (1)
Event • Response
If a riddle is played, spot Gollum to make a minion fierce until the regroup phase.
’It must give us three guessesses, my precious, three guessesses.’
H1 C 135

Not A Riddle (2)
Event • Response
If a riddle is played, spot Gollum to choose one: shuffle your draw deck; count the number of cards in your hand, place your hand beneath your draw deck and draw the same number of cards; or play a maneuver event from hand (suspending the current riddle until the event is resolved). This can change the effects of that riddle.
’It must give us three guessesses, my precious, three guessesses.’
H1 C 135

The problem with your wording SoP and Dain for Three Guessesses is then it doesn’t work as defence against your opponent’s riddles, and I wanted it to do both. Any suggestions that make that work as well?

Empty Holes Filled
Event • Maneuver
Riddle.
To play, spot Gollum.
Choose an opponent and name a number. Then reveal the top 5 cards of their draw deck. If the named number matches the number of Free Peoples cards revealed, you may exert a companion. If it does not, heal a companion.
’It comes first and follows after, / Ends life, kills laughter.’
H1 C 129

Silent Mail
Event • Maneuver
Riddle.
To play, spot Gollum.
Choose an opponent and name a number. Then reveal the top 5 cards of their draw deck. If the named number matches the number of possessions revealed, you may draw 3 cards. If it does not, discard one of your possessions or conditions.
’Never thirsty, ever drinking, / All in mail never clinking.’
H1 U 140

Watching Silently
Event • Maneuver
Spot Gollum to look at the top 6 cards of a player’s draw deck. Replace them in the same order.
Bilbo could not see him, be he was wondering a lot about Bilbo, for he could see that he was no goblin at all.
H1 C 145

Thanks Dain, changed it.

Now for the next riddling theme:

Empty Holes Filled
Event • Maneuver
Riddle.
To play, spot Gollum.
Choose an opponent and name a number. Then reveal the top 5 cards of their draw deck. If the named number matches the number of Free Peoples cards revealed, you may exert a companion. If it does not, the Free Peoples player may heal a companion.
’It comes first and follows after, / Ends life, kills laughter.’
H1 C 129
cool

Silent Mail
Event • Maneuver
Riddle.
To play, spot Gollum.
Choose an opponent and name a number. Then reveal the top 5 cards of their draw deck. If the named number matches the number of possessions revealed, you may draw 3 cards. If it does not, discard one of your possessions or conditions.
’Never thirsty, ever drinking, / All in mail never clinking.’
H1 U 140
I guess

Watching Silently
Event • Maneuver
Spot Gollum to look at the top 6 cards of a player’s draw deck. Replace them in the same order.
Bilbo could not see him, be he was wondering a lot about Bilbo, for he could see that he was no goblin at all.
H1 C 145

Deadly Cold
Condition • Support Area
When you play this condition, you may spot Gollum to add a token here for each underground site you can spot.
Maneuver: Remove X tokens from here to reveal the top X cards of a player’s draw deck.
Suddenly without any warning he trotted splash into water! Ugh! it was icy cold.
H1 C 128

• Subterranean Lake
Condition • Support Area
While at an underground site, each event’s twilight cost is -1.
While at a lake or river site, Gollym is fierce.
Maneuver: Discard this condition to reveal a player’s hand.
... for lake it was, wide and deep and deadly cold.
H1 R 141

And before you point it out, lake is a new terrain keyword found on various sites in the set, including (unsurprisingly) Gollum’s Pool and The Long Lake.

• Rotting Boat
Condition • Support Area
Each a riddle is played and you can spot fewer than 3 cards stacked on this condition, you may spot Gollum to stack that riddle here.
Maneuver: Exert Gollum and remove to take your card stacked here into hand.
He had a little boat, and he rowed about quietly on the lake...
H1 R 139