(maybe everyone should roll initiative)

Well if you insist:

Bow initiative: 11

Petcan initiative 15 

14Initiative

There goes our carefully planned surprise attack. 

Initiative 6

Zenodor and Irraxan will stick together at the back, keeping the magical darkness spell. (which gives disadvantage to anyone trying to him Z with an attack - assuming they even know where he is in the first place) 

Brother Randall’s Initiative:  20

Tentacle Monster 1: 6

Tentacle Monster 2: 16

Initiative Order:

Randall
Tentacle Monster 2
Petcan
Tempe
Bow
Zenodor
Tentacle Monster 1

(ooc: you should roll initiative for Irraxan and I'll add him into the init. order)

(Randall is up.)

Randall:

Not sure exactly what is going on, Randall nonetheless reacts quickly to the cessation of footsteps ahead.  As he follows along just behind the back border of the darkness, he casts Bless on the three closest members of the party—Petcan, Tempe, and Bow.

Quote from Brian_Avery >>

(ooc: you should roll initiative for Irraxan and I'll add him into the init. order)

(Randall is up.)

 Good point. I forgot he gets his own roll.

Irraxan's initiative is 15

Tentacle Monster 2 moves up and attacks Pinky.

Attack: 13 Damage: 10

Attack: 13 Damage: 7

Initiative Order:

Randall
Tentacle Monster 2
Petcan
Irraxan
Tempe
Bow
Zenodor
Tentacle Monster 1

The tentacle monster misses Pinky with both pincer attacks.

(Petcan is up.)

Petcan casts fire bolt across the two tentacle creatures 

Attack: 12 Damage: 11 

Attack: 9 Damage: 13 

Quote from nschrock >>

Petcan casts fire bolt across the two tentacle creatures 

Attack: 12 Damage: 11 

Attack: 9 Damage: 13 

 OOC:  Remember to add d4 to your attacks, as you are Blessed!

Pinky teleports away DC15 save or take 7 for 15ft back then retreats into the darkness

ooc: Btw what is the situation? With the darkness can we even see these things?

(fire damage)

Irraxan stays by Z and doesn't take any action, other than Dodge - just in case.

Regarding the darkness: the Darkness 15ft around Irraxan is magical, so impenetrable to normal Darkvision or most other means. This means you would be subject to condition 'Blinded' inside it. However, the enemy also is unlikely to be able to see you unless they are close enough and have Tremor Sense or Blindsight or similar.

Zenodor and Irraxan both have Devil's Sight which allows them to see normally through magical darkness, so are unaffected.

OOC:  Also, if you are within 15 feet of Randall, you can see normally as if in normal torchlight, as the light from his glowing weapon is both magical and not a spell of 2nd level or lower, so it should penetrate the darkness (but not dispel it, so only lights the portion of the darkness within 15' of his weapon).