As Dusk Falls

Jay and Vanessa will eventually reach a campground together in Chapter 5 if you have taken her along for the ride the whole way. In order to earn this achievement, dont risk telling her the truth, and then stay as friends. After some dialogue choices, you will have the choice to take Vanessa to Canada or go without her. Choose no it's too dangerous when she asks you to take her.

If you end up on a cliff with Vanessa after visiting Todd, the only thing you have to do to get this achievement is tell her that she's not allowed to come with you because it's too dangerous. It doesn't matter if you stay friends or kiss her. It doesn't matter if you come clean or keep lying to her. All that matters is that you refuse to let her come with you.

For what it's worth, I did not act like a hothead at the party, I let Vanessa handle Todd and respected her wishes when it came to how to move forward. I told her the truth, and I kissed her back. But when she told me she was coming with, I refused, for fear of her safety. That's how I personally got the achievement.

In Chapter 5 after the party tell Vanessa not to come to Canada.

For a Full and Fast Achievements Guide check the link below:


Timestamps:

00:00 Intro + Useful Information
02:02 Chapter 1: Story
03:49 Chapter 1: Code Breaker + Smooth Criminal Achievements
05:14 Chapter 1: Message Received + Tables Turned + And So It Begins… Achievements
06:32 Chapter 1: Bungled Achievement
07:16 Chapter 1: Cop Out + Point Blank Achievements
08:18 Chapter 2: What’s Your Emergency? Achievement
09:12 Chapter 2: Story
10:08 Chapter 2: Paging Dr. Walker Achievement
10:57 Chapter 2: Keeping The Faith + Second Chance + Lifesaver Achievements
11:56 Chapter 2: Dodged A Bullet + Caught in a Trap Achievements
12:21 Chapter 2: What’s Done is Done + Unforgiveable Achievements
13:32 Chapter 3: Long Arm of the Law
14:01 Chapter 3: Story
14:24 Chapter 3: Resurrection Achievement
14:48 Chapter 3: Take Me Instead + New Dawn + From Dusk ‘til Dawn Achievements
15:59 Chapter 3: Better the Devil You Know Achievement
16:23 Chapter 3: Buried Alive Achievement
16:44 Chapter 3: She’s Coming with Us Achievement
17:18 Chapter 4: Invincible Achievement
17:49 Chapter 4: Story
18:46 Chapter 4: Cabin? What Cabin? + Brothers in Arms + Into The Woods Achievements
19:46 Chapter 4: Trail of Breadcrumbs + Once a Holt + Hands in the Air + No Going Back Achievement
21:19 Chapter 5: Bullseye Achievement
22:04 Chapter 5: Plead the 5th Achievement
22:28 Chapter 5: Story
22:54 Chapter 5: Jailbird Achievement
23:23 Chapter 5: Heart to Heart + Bonnie and Clyde + Runaways Achievements
24:14 Chapter 5: Cuba Libre Achievement
24:58 Chapter 6: Story (Wait for the Cop)
25:43 Chapter 6: Into the Wild + Breaking Bread + Past, Tense + End of the Road? Achievements
26:56 Chapter 6: Almost Made It + Enough is Enough + Stay of Execution
27:47 Chapter 6: You’re On Your Own (Chapter5) + Free Bird + Most Wanted Achievements