The Four Sons of Dating

The Haggadah introduces us to four sons—each with their own way of approaching the Pesach story. And let’s be honest, we’ve probably dated all four of them. But beyond the humor, these archetypes offer insight into the different ways people show up in relationships and how we can navigate dating with more wisdom and self-awareness. No one fits perfectly into a single category, and even the “difficult” types often have redeeming qualities. But recognizing these patterns can help us make better choices, not just about who we date, but about how we date.

The Wise One

He asks deep, intentional questions. He wants to understand you, your values, your goals. He reads dating books, listens to relationship podcasts, and genuinely wants to build something meaningful. Dating him feels steady, thoughtful, and secure. He’s the kind of person who takes relationships seriously—sometimes to a fault.

The challenge? His desire to “get it right” can lead to overthinking. He sends follow-up texts analyzing your last conversation or seems to be looking for commitment unnaturally early. His wisdom is valuable, but if taken too far, it can make dating feel like a structured checklist rather than a natural, evolving connection. And sometimes, he struggles with emotional spontaneity. He wants to approach dating with intelligence, but relationships aren’t just intellectual exercises—they require heart, risk, and a little bit of unpredictability.

That said, his depth and sincerity are rare qualities. If he can learn to trust the process and let go of the need for control, he has the potential to build something real.

💡 Dating lesson: Appreciate wisdom, but don’t let analysis replace emotional connection. Relationships are built in the real world, not just in theory. If you’re dating someone like this, help him feel safe being present rather than always looking ahead. And if you’re the one stuck in analysis paralysis, remind yourself that love isn’t a perfect formula—it’s a lived experience.

The Wicked One

She knows the rules but doesn’t care. She plays games, avoids commitment, and somehow always keeps you guessing. Maybe she’s emotionally unavailable, or maybe she enjoys the chase more than the relationship itself. Either way, you’re left feeling drained.

Not every “wicked” dater is intentionally hurtful. Some have been hurt themselves, leading them to build walls rather than bridges. Others are still figuring out what they want, experimenting with different relationship dynamics, or just caught up in their own self-exploration. They might not even realize the impact they’re having on others. They’re not necessarily cruel, but they are self-focused in a way that makes genuine connection difficult.

The real issue is that dating someone like this can lead you to internalize their ambivalence. If they’re inconsistent, you might find yourself constantly analyzing their actions, looking for hidden signs of interest, or making excuses for their behavior. The truth is, if someone really values you, you won’t have to guess.

💡 Dating lesson: Don’t try to change someone who isn’t showing up for you. If someone makes you feel uncertain or undervalued, that’s your sign to walk away—not because they’re inherently bad, but because a healthy relationship requires two people who are equally invested. If you find yourself stuck in a cycle of hoping someone will come around, ask yourself: Are you waiting for something that may never happen? And is that the kind of love you truly want?

The Simple One

He’s kind, easygoing, and means well—but he’s not exactly intentional. He goes with the flow, doesn’t think too far ahead, and isn’t sure what he wants. He likes you, but if you ask where things are going, he shrugs. He’s not playing games, but he’s not leading the way either.

The simple dater can be frustrating because he’s almost what you want—sweet, present, and not intentionally hurtful. But without clarity and direction, you might find yourself stuck in a cycle of “seeing where things go” instead of actively building something real. And that can be even more painful than outright rejection. It’s hard to walk away from something that kind of works, even when deep down, you know you need more.

That said, not everyone who lacks direction is a lost cause. Some people need time and encouragement to develop clarity. If he’s open to growth and willing to engage in real conversations about the future, he may surprise you. But if he consistently avoids these conversations or leaves you feeling uncertain, it’s worth asking yourself whether waiting around is in your best interest.

💡 Dating lesson: If you’re looking for a serious relationship, clarity matters. A relationship without direction won’t magically find one. If someone isn’t willing to take the next step, you don’t have to wait around hoping they’ll figure it out. But before writing someone off, consider whether they’re truly indifferent or just need help articulating what they want.

The One Who Doesn’t Know How to Ask

Se wants to connect but doesn’t know how. Maybe she struggles with communication, has never been in a serious relationship, or isn’t sure how to express her feelings. She’s a good person, but understanding her can feel like solving a puzzle.

There are different types of daters who “don’t know how to ask.” Some are simply inexperienced and need time to learn. Others may have deeper struggles—whether social anxiety, past trauma, or emotional barriers that make vulnerability difficult. They might want love but feel too afraid to step into it fully.

Dating someone like this requires patience, but it also requires boundaries. If you’re constantly guessing what they’re thinking, trying to coax emotions out of them, or making excuses for their lack of effort, that is not a sustainable dynamic. Relationships work best when both people are willing to show up, even when it’s uncomfortable.

On the flip side, if you’re someone who struggles to express yourself, know that relationships require some level of openness. No one can read your mind, and if you want to build something real, you have to take risks.

💡 Dating lesson: Communication is key. If you feel like you’re always guessing what the other person is thinking, that’s not sustainable. Relationships require mutual effort. If you’re dating someone who struggles with communication, be patient but also honest about your needs. And if you’re the one who finds communication hard, ask yourself: What small steps can you take to bridge that gap?

At its core, the Haggadah teaches us that every person has a different way of engaging with the world. Some are proactive, some are distant, some are uncertain. And sometimes, we even embody different aspects of these four sons at different points in our own dating journeys.

The real question is: What patterns have you fallen into? Are you constantly giving the benefit of the doubt to someone who isn’t showing up for you? Are you getting stuck in analysis paralysis? Are you waiting for clarity from someone who isn’t offering it? Can you approach dating with intention, honesty, and self-respect?

Pesach reminds us that we don’t have to be stuck in the same patterns year after year. The same way Bnei Yisrael broke free from slavery and stepped into something new, you have the power to rewrite your dating story. The right person won’t leave you questioning your worth or your future. So this Pesach, take a moment to ask yourself: What kind of person do I truly want to build a future with? And am I making space for that person in my life?