What I'd like to start off saying is that Gemini and Pisces are both incredibly, incredibly, incredibly empathetic people. However! They are zodiac signs who practice empathy using very different methods.
Gemini operates from curiosity. For a Gemini, asking you questions is how they relate to you. They'll ask you all kinds of questions, tame and totally inappropriate. "Did you have sex last night with your new boo?", "How much money do you make and how much did you expect to make when you got your job?", and "Did you hear what so and so said about you last week?"
If Gemini's questions put you on edge, then you should keep in mind that Gemini doesn't always need you to answer their every line of questioning. They're not trying to shake you down for information or mess with you head. They are trying to make you feel like someone is paying attention to you, like you're not so alone out here because someone wants to know stuff about you. That's all.
Pisces operates from a place of tolerance. Pisces doesn't always ask a whole lot of questions. They don't need to because they actually see what you're not saying with their eyes. If you pause between words and change your sentence, Pisces hears that. If you avoid an explanation, then Pisces hears your discomfort. They don't need to ask you a bunch of stuff because they can already make you guess.
And if a Pisces's eerie ability to read you in real time creeps you out, then keep in mind that Pisces is only giving you so much attention because they also don't want you to feel alone when you're with them. They want to you to remember that someone is here with you, that you haven't been forgotten about or unaccounted for.
You might notice—the way that a Gemini gives empathy is drastically different from how a Pisces does it. A Gemini likes to say, "What the hell's been going on with you? Tell me everything." A Pisces likes to say, "I understand you already. Don't worry."
Gemini, an air sign, is squared with Pisces, a water sign. There's a pretty basic clash between the two signs that looks something like this:
Gemini wants to know more about Pisces and asks a lot of active, teasing, direct and indirect questions. Pisces keeps giving vagueness or says that they don't know. They deliver vulnerability when Gemini doesn't notice and they evade when Gemini pays too much attention. Gemini thinks that Pisces is distant while Pisces feels put on the spot by Gemini's multiple and, frankly, weird lines of questioning. Why the hell does Gemini need to know so much about me? Do they truly just not get it?
Pisces tries to tell Gemini that they are understood without having to explain. Gemini feels smothered because explaining themselves is actually just part of how they operate emotionally. They want that kind of Socratic thing that air signs do where they mirror emotions dialectically by dialogue and will simply make up an imaginary friend if they don't have someone to talk to. When Gemini tries to explain themselves to Pisces, Pisces sees their nervousness first and tries to assure them that they don't need to—Pisces already accepts them as is.
Honestly, these two signs can really make it work. You have to remember that squares, in astrology, give you a lot of energy. Yes, conflict, open and otherwise. Yes, direct confrontation and interest. Gemini and Pisces are different and they can interest each other.
You'll probably already notice that Pisces can run into a trap of their own making. Because they can often accurately guess at what someone else is feeling, they often end up trying to manage other people's feelings. What Gemini can do is offer them a reprieve. A Gemini doesn't expect anyone to guess at their feelings. They have this almost naïvely innocent quality about them when it comes to emotional investigation, as though they're only just finding out that they have a psychic underlayer each time they run into it.
That can make Pisces laugh. Pisces, who sees that psychic underlayer, will find Gemini really funny because the way that Gemini approaches stuff—light, curious, and innocent—is really relaxing.
You'll also notice that Gemini can run into a trap of their own making. Sometimes, when a Gemini faces deep shit that they need to confront, they actually use their loose charm to pay much more attention to what's going on with other people and how they might be of help than to their own stuff. That's why a Gemini can usually recognize a character trait that it shares with Pisces—the tendency to forget the self for someone else's sake. Because this tendency is shared, Pisces doesn't let Gemini get away with self abandonment. It, again, has clocked everything a Gemini has going on deep down inside and Pisces finds a way to give that hidden self attention.
Pisces can make a Gemini very intensely interested—more self curious, less distracted, and more open to challenges that they didn't know they were putting off.
There's something that draws Gemini and Pisces to each other. If you always treat squares, because squares are hard aspects as negative, then you might lose out on some of the great things that squares can offer two signs. Sure, Gemini and Pisces's style of empathy can conflict with each other's but that's often why they work—why they communicate well.
There's also the dynamic that any Mercurial will have with any Jupiterian. You see, Jupiter really likes Mercury. Mercury has very different powers from Jupiter but it has gall, it has gait, and it has gab. Usually, Jupiterians will feel very charmed by Mercurials even when said Mercurial makes very different decisions than the Jupiterian would.
What I'm trying to say is that Gemini, as a Mercurial, can sometimes get away with a lot of mischief with Pisces that other signs might not. Why? Because Gemini is funny and Pisces happens to love funny people. Pisces is not a rigid personality. It likes people who make them laugh, tease them, and give them pleasure. In terms of pleasure, Gemini can deliver.
When it comes to friendship, sex, or family—you'll find that Gemini and Pisces can have a lot of fun together. Sure, there will be the constant friction. Pisces will do some wild shit and Gemini will wonder, "Does this person even live in reality?" Gemini will say something shocking and Pisces will think, "Okay, this person lives in a totally different reality than me."
But—vibe wise—Gemini and Pisces are here to have a good time together. They're making each other giggle and, both being quite transparent, sharing gossip that neither of them should share. Even though they can inhabit different realities, they somehow make each other feel like they're truly in on something together. That's because, even when someone's style of empathy is different from your own, you can feel that they are trying to get you when they do.