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You’ll first meet Judy during the Main Job The Information, after which she’ll have her own Main Job questline which you can start after completing Playing for Time. Judy’s Main Job questline consists of the following quests:

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Complete all those Main Jobs, then start [M’ap Tann Pelen] and progress it at least until you get a call back from Mr. Hands. Sometime after that (skip time if you must) Judy should call you and ask you to come over, starting the first of her Side Job questline, which consists of the following quests:

You’ll need to complete this Side Job questline to romance Judy. Only female V (feminine voice and body) can romance Judy.

Judy’s romance seems more difficult than it actually is, possibly because of how hot-headed she can be. To calm your fears, however, know that it’s very, very difficult to botch Judy’s romance… if you don’t want to. That said, there are multiple opportunities to do so, but most of them are painfully obvious. During many of her Side Jobs, you’ll get the option to outright refuse to participate, which will kill the questline and end any possibility of romancing Judy, but so long as you participate and finish her Side Jobs, very little else matters, even when it seems like it should.

Being rude, confrontational or accusatory with Judy, being insensitive about Evelyn, not taking her side when talking to Fingers, not helping her with her revenge against Woodman… none of these matter. In fact, there’s only one rare exception where you choice really does matter during the Side Job Pisces. Near the end of this quest you’ll get the choice to fight the Tyger Claw bosses or help Maiko seize control of Clouds. If you do the latter, you must not take the reward she offers afterwards, otherwise Judy’s questline will end. Aside from outright non-participation, this is the one choice that seems to matter leading up to Pyramid Song.

During Pyramid Song, it’s mostly more of the same during the start of the quest - do what Judy wants, go diving with her, and after the dive is over go outside and turn on a generator. After this, head back into the bungalow and knock on the bathroom door to check up on Judy, then head inside, sit down, and talk to her. When a timed dialogue check pops up you’ll get a chance to determine where your relationship with Judy goes.

During this timed dialogue decision pick the option [Touch] “It is ours.” to sleep with Judy. If for some reason that’s too obvious and easy for you, you can also pick [Comfort] “Why didn’t you wanna tell me?” followed immediately by [Kiss] Stop thinking about it.“. If you do not follow up [Comfort] “Why didn’t you wanna tell me?” with [Kiss] Stop thinking about it.“ you’ll botch the chance to romance Judy.

After sleeping with Judy, you’ll wake up in the bedroom the next morning. Grab your clothes and go talk to her outside where you’ll get another two dialogue options. Respond to her query with “The beginning of something amazing.” and you’ll seal the deal and end up in a romantic relationship with Judy. If you pick “A pleasant distraction”, you’ll anger Judy and ruin your chance to romance her at the very last moment.

That’s all there really is to it; complete all her Side Jobs, say and do pretty much whatever you want throughout them. The biggest way to fail to romance Judy is by simply refusing to participate and ending her questline early. Don’t put Maiko in charge of Clouds, and if you do, don’t take the reward she offers, and during Pyramid Song just pick the dialogue options [Touch] “It is ours.” and “The beginning of something amazing.”.

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