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There's an old vault down there that they use as a base. I told Nick he was walking into a trap, but he just smiled and walked out the door like he always does.Ellie Perkins

Unlikely Valentine is a main story quest and achievement/trophy in Fallout 4.

Quick walkthrough

Main quest: Unlikely Valentine 
Travel to Park Street station
Enter Vault 114 and find your way to Nick Valentine
Release Nick and follow him to the entrance of the vault. 
Confront Skinny Malone
Leave the station and talk with Nick. 
Reward: 200+ XP
100 bottlecaps
Worn fedora
Faded trench coat 
Leads to: Getting a Clue 

Detailed walkthrough

After speaking to Ellie Perkins, it is revealed that Nick Valentine is being held captive in Park Street station. The station is filled with Triggermen, but inside the station is the entrance to Vault 114.

The vault is guarded by Triggermen armed with submachine guns, 10mm pistols, and at higher levels, .44 pistols. The Sole Survivor needs to fight their way through the vault until they come to a large open atrium. Guarding the overseer's office, where Nick is being held, is a Triggerman named Dino. Sneaking close allows the player character to listen to the conversation between the two of them where Valentine convinces Dino that a crime boss is upset at him about his cheating habit during gambling. Dino then runs out of the room to square things off with said crime boss, leaving the coast clear to free Valentine. Alternatively, Dino may be killed without waiting for him to leave. The control panel next to the office door can then be used to free Valentine.

Speaking with Nick reveals why he is there and that they should leave as soon as possible. On the desk behind him is the speech bobblehead. After talking with Nick, he will take the lead out of the vault where Skinny Malone and Darla will be waiting to stop the escape. With a few speech checks it is possible to turn them against each other or leave the vault without fighting at all. If a certain stage of the unmarked quest, The Sight has been completed before coming to the vault, there will be an additional speech option that allows escape without any violence and Darla will depart also, as Skinny Malone will advise they have 10 seconds to leave. Otherwise, the Sole Survivor and Valentine will need to kill Skinny Malone and his companions in order to leave.

After exiting the vault there is a short conversation with Valentine where he directs the Sole Survivor to meet him back at his office in Diamond City. Upon arrival, speaking with Ellie will end the quest.

Companion reactions

EventCaitCodsworthCurieDanseDeaconHancockMacCreadyPiperPrestonStrongValentineX6-88LongfellowGage
Respond sarcastically to Darla when she is instigating a fightLikeDislikesNo reactionDislikesLikeLikeLikeDislikesDislikesLikeNo reactionNo reactionNo reactionLike
Try to talk Darla down from a fightDislikesLikeLikeLikeLikeNo reactionDislikesLikeLikeDislikesNo reactionNo reactionLikeDislikes
Attempt to end the situation with Skinny Malone peacefullyDislikesLikeLikeLikeLikeDislikesDislikesLikeLikeDislikesNo reactionNo reactionLikeDislikes
Insult Skinny MaloneLikeHatesDislikesDislikesDislikesLikeDislikesDislikesDislikesLikeNo reactionNo reactionNo reactionLike
Attempt to turn Skinny against DarlaDislikesLikeDislikesDislikesLikeLikeDislikesLikeLikeDislikesNo reactionNo reactionNo reactionLike
Attempt to trick Darla into shooting SkinnyLikeHatesDislikesDislikesLikeLikeLikeDislikesDislikesLikeNo reactionNo reactionLikeLike
Remind Skinny of his past with Nick ValentineDislikesNo reactionNo reactionLikeLikeNo reactionDislikesLikeLikeDislikesNo reactionNo reactionLikeNo reaction

Quest stages

Quest stages
StageStatusDescriptionLog Entry
10 Find Nick ValentineNick Valentine apparently went missing while investigating a case. If I want his help in locating Shaun, I'll need to find him first. His last known location was Park Street Station.
20 Free Nick ValentineI've found Nick Valentine, but he's being held prisoner by some thugs in Park Street Station. I need to get him out of there.
30 Talk to Nick Valentine
50 Follow Nick ValentineI've freed Nick Valentine and filled him in on my situation. He'll help me find Shaun, but first we need to get out of this station.
100 Leave the station
110 Talk to Nick Valentine
210Quest finishedQuest completeI've rescued Nick Valentine and we've escaped from Park Street Station. Now he's free to help me find Shaun.

Notes

  • Even if one hides from or otherwise avoided Dino so he leaves the room alive, Nick will still say it won't be long till the others realize "muscle for brains" (Dino) isn't returning. Furthermore, he will simply wait in a side room off the hallway, where he will likely detect the player character and turn hostile.
  • Even if one is not detected at all and doesn't kill any of the Triggermen in the dining area where Nick asks how the player character wants to "play this" he will still comment on the "loud and hard" methods upon leaving the area.
  • In the same room as Nick, the player character can find the Speech bobblehead sitting on the overseer's table.
  • While escorting Nick, Astoundingly Awesome Tales #8 can be found on a pile of boxes blockading a hallway, before going through a bedroom.
  • If the player character ends the conflict with Skinny Malone peacefully, attacking him, Darla or the remaining Triggermen while they are not hostile does not count as murder in the Pip-Boy's crime statistics.
  • Frequently, after convincing Skinny Malone of letting the player character go peacefully, a companion will just walk instead of run to the exit. They end up still near the thugs when the countdown ends and get involved in a firefight. Unless one is playing in Survival and doesn't want to spoil their previous diplomatic success, it is best to simply leave, as the companion will teleport to their side.
  • If the Sole Survivor frees Nick without meeting Ellie Perkins first, the quest Jewel of the Commonwealth will be auto-completed (or skipped entirely if one didn't pick up the specific quest from Mama Murphy or meeting Piper) and they will gain a unique speech option.
  • This is the farthest point in the main quest that the player can skip around to after exiting Vault 111 without console commands or mods.

Bugs

  • PCPC Xbox OneXbox One When confronted by Skinny Malone and Darla, the accompanying Triggermen will become hostile if a targeting helmet is worn. Removing it will suffice. The highlight ability from Berry Mentats seems to make them hostile as well. [verified]
  • [Platforms needed] Nick will turn hostile and shoot Skinny Malone and Darla but will not shoot the Triggermen.[verified]
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