Dead Age
77 Achievements
GOG
Romance Jennifer
Complete the game in love with Jennifer.
7.2%
How to unlock the Romance Jennifer achievement in Dead Age - Definitive Guide
Make sure that on Day 32 you choose to spend your time with her Jennifer (providing she is in your group), then when you finish the game this achievement should pop
During the course of a playthrough of Dead Age, you'll be able to get everyone in game to join your camp minus three people (so you can get max nine of twelve characters in one run). Of the missing three, two will be from the "random pool" (listed below) and one will either be James or Mary (when you do the mission to save one, the mission to save the other disappears.
The list of random characters is as follows: Bill, Hank, Lydia, Jamal, Jennifer, Larissa, Liz
Jennifer is one of these random characters, so is not guaranteed to be available as a camp follower. Should he show up, you have three chances for that to happen the first week of the game (Day 1 - 7), and another early in week two (Day 7-14). After that, only one more "random" character will show up late in the game (around Day 28 - Day 32). Therein, if you're going for this achievement specifically, if you don't see the Jennifer quest by Day 10 or so, restart your game.
Jennifer
If Jennifer is one of your random ally assignments, Trish will ask you to meet Jennifer outside of camp. Once there, you, Trish, and Jennifer will be forced to fight three waves of Punks. If it's very early in game, this fight may be difficult, so make sure you have med packs ready and feel free to use ammo liberally. Upon defeating all three waves of punks, Jennifer will join your camp.
Later in game, Jennifer will ask you to help her attack the military base at the end of Highway Day. Make sure you do so, both for the Tools rewarded and to make sure her romance option is available on Day 33.
If you followed the above, once you reach Day 33, you'll be given the option to romance Jennifer (and possibly Larissa or Lydia) or have no romance option at all, with each choice having a corresponding achievement tied to it. Since Lydia appears in camp when RNG selects either Hank or Lydia to be one of your RNG camp followers, its best to romance Larissa or Jennifer first if available, as Lydia is available more often and "no romance" is always an option.
The achievement itself will unlock on Day 42 upon reaching one of the "Successful" endings of the game (it won't unlock on one of the "Bad" endings).
The list of random characters is as follows: Bill, Hank, Lydia, Jamal, Jennifer, Larissa, Liz
Jennifer is one of these random characters, so is not guaranteed to be available as a camp follower. Should he show up, you have three chances for that to happen the first week of the game (Day 1 - 7), and another early in week two (Day 7-14). After that, only one more "random" character will show up late in the game (around Day 28 - Day 32). Therein, if you're going for this achievement specifically, if you don't see the Jennifer quest by Day 10 or so, restart your game.
Jennifer
If Jennifer is one of your random ally assignments, Trish will ask you to meet Jennifer outside of camp. Once there, you, Trish, and Jennifer will be forced to fight three waves of Punks. If it's very early in game, this fight may be difficult, so make sure you have med packs ready and feel free to use ammo liberally. Upon defeating all three waves of punks, Jennifer will join your camp.
Later in game, Jennifer will ask you to help her attack the military base at the end of Highway Day. Make sure you do so, both for the Tools rewarded and to make sure her romance option is available on Day 33.
If you followed the above, once you reach Day 33, you'll be given the option to romance Jennifer (and possibly Larissa or Lydia) or have no romance option at all, with each choice having a corresponding achievement tied to it. Since Lydia appears in camp when RNG selects either Hank or Lydia to be one of your RNG camp followers, its best to romance Larissa or Jennifer first if available, as Lydia is available more often and "no romance" is always an option.
The achievement itself will unlock on Day 42 upon reaching one of the "Successful" endings of the game (it won't unlock on one of the "Bad" endings).