Shterna has been on six dates with Naftali, and on paper, things are going well. He’s kind, thoughtful, and easy to talk to. She finds herself wanting it to work—but there’s a growing sense of unease she can’t quite name. The more serious the relationship becomes, the louder the quiet discomfort grows.
After a deep conversation with a coach, something clicked: Naftali is nothing like the men she grew up around. Her father, her brothers—they shaped her image of what a man should be. And even though Naftali treats her well and their dates go smoothly, part of her keeps holding back, unsure. It’s as if one part of her is moving forward while another part is quietly resisting.
This inner tug-of-war is more common than it seems. When two parts of us want different things, it can create confusion, hesitation, and self-doubt. Shterna’s story is one example of how shidduchim can stir up deeper questions—not just about the other person, but about who we are and what truly matters to us.
What it means to be conflicted
Internal conflict in shidduchim can show up in many ways. Sometimes, a match feels right to you, but you’re worried about disappointing your parents. Other times, you may genuinely want to move forward, but feel held back by guilt over what you were taught in yeshiva or seminary. Or maybe you’re drawn to a certain type of person—someone who wants to stay in learning long-term, for example—but you feel too nervous to take the leap, unsure if you’ll be able to handle it or afraid you’ll regret it later.
In situations like these, you might start off feeling confident that this is the kind of person or lifestyle you’re looking for. But as things get more serious, that small questioning voice inside grows louder, and you start wondering whether it’s something you can really ignore.
When push comes to shove, it’s easy to lose your nerve. You’re facing a lifelong decision, and the thought of closing the door on something deeply ingrained in your mind can be unsettling. You might find yourself torn between what calls to you personally and the ideals you were taught or raised to value, pulled between what you believe will bring you happiness and what feels “right.”
Shidduchim have a way of pushing us to confront deep questions about who we really are and what we truly value. Often, dating brings out unexpected and complicated feelings and thoughts, catching us off guard when we thought we had it all figured out.
The kind of conflict we’re talking about here is different from the usual uncertainty many people experience in shidduchim. It’s normal to wrestle with choices, weigh priorities, and consider pros and cons. Anyone, no matter their personality, can face tough, knotty decisions during dating.
What we’re addressing here is a deeper, more persistent conflict—a dichotomy that often leaves a person stuck. It happens because something fundamental is still unresolved. They’re caught between trying to please both themselves and society, or themselves and their family. Sometimes, these competing values have been internalized, and now they’re struggling to reconcile two parts of themselves pulling in different directions.
Dating can leave you caught between two voices: one insists, “You know what’s ‘right’—stick to it,” while the other quietly whispers, “This doesn’t feel fully true for me.” As a result, you feel deeply conflicted, and dating can become confusing and difficult.
Dating can leave you caught between two voices: one insists, “You know what’s ‘right’—stick to it,” while the other quietly whispers, “This doesn’t feel fully true for me.” As a result, you feel deeply conflicted, and dating can become confusing and difficult.
What it can be like dating while being conflicted
We all want to be happy while dating. We want to meet the one person who not only fits, but truly feels right. But if someone’s complicated, that can make things complicated.
When your internal world is split, even if many aspects of the dating are going well, it can feel rather uncomfortable. Here are some of the ways this can affect you:
Not knowing what to look for — Because your criteria come from two different maps, you question what to prioritize. You may take a position at first, only to find yourself questioning things at a later point.
Not knowing how to show up — Which version of yourself should you “be” with the person you’re dating? You may wonder whether you are showing your authentic self or being true to just a part of yourself.
Subconsciously sabotaging good dates — Pulling away, finding flaws, or disengaging when things start to get real to avoid what feels like an impossible choice.
Feeling drained or stuck — Feeling that the more you date, you only get more confused and overwhelmed, combined with the increasing pressure to decide.
Negative feelings — Struggle to feel satisfied because you feel bad that you are failing to live up to something you have some loyalty towards, generating emotions such as shame or guilt.
Inconsistent dating experience — You might be drawn to someone and feel good about it at first, only to grow increasingly restless as the shidduch progresses. You often want to make a decision but end up second-guessing yourself, with a pit in your stomach.
Easily influenced — Because you are conflicted on the inside, you are more susceptible to what people say to you. Depending on who you are speaking to on a given day, one part or another may be reinforced. As a result, you may flip-flop on what you’re looking for, depending on who you’re speaking to.
Wanting others to decide for you — Because choosing your direction in life feels too loaded or risky, you may lean unreasonably on others to lift your crippling doubt. You may even wish that someone else would just tell you what to do.
What do to if you’re conflicted
Don’t beat yourself up — This kind of identity-level confusion is not a flaw—it’s a fork in the road, one that deserves your attention. Once you’re at peace with who you are and what matters to you, you’ll be dating from a place of integrity and clarity. That’s a great gift you can give yourself and the person you eventually choose.
Figure yourself out — Dating isn’t the time or place to discover who you are; it’s the time to bring who you already are. Until your inner conflict softens—or at least becomes clearer—you’re not in the best position to make a lifelong decision. Talk with a mentor, coach, or therapist, but keep in mind it may take more than one conversation. Journaling your thoughts and feelings can also help you get closer to your truest self.
Make sure you’re ready — There’s no need to rush toward clarity, and you don’t have to pretend you’re clear when you’re not. Dating calls for a truly momentous decision, and it’s okay if you don’t feel ready yet. That’s not weakness—it’s wisdom.
Focus on what is most important to marriage — Many people have varying sides to their character, but not all aspects are equally central to the project of marriage. For example, respect, trust and communication are more crucial than fun, intellectual, or popular. In trying to make sense of your choices, identify which of the options is likely to have the biggest impact on the relationship.
Are those differences reconcilable? — Trying to figure out the two sides of an internal conflict is similar to dating someone who is different from you in certain ways and you have to work out if it’s a match. Check out what we say about handling differences in dating, and you can apply some of the same thinking here.
Don’t seek endless opinions — Shopping around for advice usually does more harm than good. It often leaves you feeling even more confused. Instead of collecting opinions, focus on finding someone who can support and guide you in discovering what you truly want, rather than just telling you what to do. Otherwise, you’ll end up just as stuck as before.
Don’t let it spill into your dating — Internal conflict is hard, but it’s still your responsibility to show up with consideration. Your discomfort is no excuse for sending mixed messages, acting erratically, or keeping the other person in limbo. That means communicating well and treating the other person with care.
Conclusion
Navigating the complexities of dating while feeling conflicted isn’t easy, but it’s also deeply human. Remember, it’s okay to take your time, ask for guidance, and honor the parts of yourself that are still sorting things out. The path to finding the right match often involves facing these inner tensions head-on—and in doing so, you learn more about who you truly are and what will bring you lasting happiness. Trust the process, and trust yourself.
