Wondering how to be sure if he’s “the one”?
You're lying in bed at 2 AM, staring at the ceiling, replaying every conversation, every text, every moment with that person you've been seeing. Your mind is spinning with questions: “Is he the one? How am I supposed to know for sure? What if there's someone better out there?” Sound familiar? We get it.
As eldest daughters, we've been trained to analyze every angle, consider every possibility, and make the “perfect” choice. But here's the thing about modern dating - the abundance of choice that was supposed to make everything easier has actually made decision-making infinitely more complicated. Which is why today we're diving into the art of making confident decisions even when you can't be 100% certain about your relationship.
Overcoming Decision Paralysis in Modern Dating and Relationships
Let's set the scene here. We're living in an era of unprecedented romantic freedom. Our grandmothers met someone in their hometown, dated for a respectable amount of time, and got married. Done. Simple. But we? We have dating apps with endless swipes, the ability to move cities for love or career, and the societal permission to wait until our late twenties or thirties to settle down. We have more options, more time, and more freedom than any generation before us.
The Hidden Cost of Having Too Many Options
Here's what nobody talks about when they celebrate our romantic freedom: the more choices we have, the harder it becomes to feel certain about any single choice. This isn't just our imagination running wild - it's a psychological phenomenon called the “paradox of choice.”
Researchers conducted a fascinating experiment at a local food market. They set up a jam-tasting booth and alternated between offering 24 different flavors and just 6 flavors. What happened? The larger selection drew more curious customers, but here's the kicker - people were ten times more likely to actually buy jam when there were only 6 options. TEN TIMES. When faced with too many choices, we either get overwhelmed and walk away, or we keep sampling forever without ever committing.
Sound familiar? In dating, this translates to endless swiping, perpetual "what if" thoughts, and the nagging feeling that maybe, just maybe, your perfect person is one more swipe away. We become so focused on finding the objectively "best" option that we forget something crucial: there is no objectively best person for you.
The truth is, when it comes to romantic partners, there's no equivalent to finding the perfect shoe size - that moment when something just fits and you know it's right. Relationships aren't about finding your missing puzzle piece; they're about choosing someone and then building something beautiful together.
Why you’re thinking about being “sure” the wrong way
Let's talk about two types of decision-makers, because understanding which one you are will change everything about how you approach relationships. Logan Ury, in her book "How to Not Die Alone," describes these as The Maximizer and The Satisficer.
The Maximizer is that friend who spends three weeks researching the perfect coffee maker, reading every review on Wirecutter, comparing specs, and agonizing over the decision. In dating, Maximizers are always looking for the objectively "best" partner - the most attractive, most successful, most compatible person they could possibly find. They struggle with commitment because they're never quite sure they've found the absolute best option.
The Satisficer, on the other hand, has a clear set of standards (the coffee maker needs to make five cups, can't be too loud, and should come in a fun color), but once those standards are met, they're willing to commit. They don't need the perfect option; they need a good enough option that meets their core requirements.
Here's the plot twist: research shows that Satisficers are actually happier with their decisions than Maximizers, even when they objectively choose a "worse" option. Why? Because once they make a decision, they stop second-guessing themselves and start enjoying what they have.
In dating terms, this doesn't mean settling for someone who makes you miserable. It means getting clear on your non-negotiables (he's kind, he makes you laugh, he shares your values) and then, when you find someone who meets those standards, choosing to be happy with that choice instead of constantly wondering if someone better is out there.
Learning to Trust Your "Good Enough" Instincts
We need to have an honest conversation about the word "sure." When our community asks us, "How am I supposed to be sure he's right for me?" they're usually looking for some external validation, some sign from the universe, some guarantee that they're making the right choice. But here's what we've learned: "sure" isn't something that comes from the world around us. It's something that comes from within us.
We think that when we find the right person there will be zero doubts in our mind that they are our person, ad infinitum, forever. Now, this is something that if you speak to couples who have been happily married for 50 years, they normally have something to say about. Most happy couples, at least the ones I’ve spoken to, that there have been plenty of difficult moments throughout their marriage no matter how happy and stable. The most important type of these difficult moments is when it puts you and your partner at odds - you want different things or someone hurt the other one. When I have spoken with couples we’d typically consider “successful,” long term, happy relationships, the story I usually hear is some version of: “Yes, it was tough but when I thought about my options, life with her, even if it meant compromising on X, was always going to be worth it.”
Now you may be thinking, “Samantha, I’m not happily married dealing with whether or not to move for some job my husband was offered. I’m just dating guys and trying to figure out if this very imperfect man in front of me is worth investing in.”
But I’d like to focus you on what’s similar about these scenarios. You are at a moment where you have to decide to continue to commit yourself. Whether from the 1st date to the 2nd or from the 73rd time you and your husband have argued about responsibility to the 74th, our relationships are made up of over and over again deciding to recommit.
Life is unpredictable. We have no idea what tension will arise in the future. What betrayal or pain or disappointment we might face. We don’t know how we will grow and change and we definitely don’t know how a potential partner might grow and change.
The good news is, we don’t have to know the future to be able to make a decision right now.
We can make it easier on ourselves by just focusing on whether, given the information we have right now, this is somebody we want to continue to invest in. And give ourselves permission that the decision may not be the same tomorrow or in 10 years and that doesn’t make it the wrong decision right now.
Being "sure" is actually a decision you make, not a feeling you wait for. It's choosing to believe that the person you're with is worth investing in, worth building something with, worth the risk of vulnerability. It's deciding that this is what’s right for you right now and trusting future you to be able to make adjustments if that no longer continues to be the case.
This doesn't mean ignoring red flags or staying with someone who treats you poorly. If something genuinely concerning comes up - if he's dishonest, disrespectful, or fundamentally incompatible with your values - you have to distinguish that from just a general decision paralysis of relationships involving future uncertainty and not knowing what the future holds.
If you're constantly looking for signs that you might not have found the "best" option for you, you will always eventually find them. There will always be someone who doesn’t do that one annoying thing (but secret is, they’ll do something else annoying you might not know you don’t like yet. There are always taller, funnier, more successful, or more adventurous people. The question isn't whether someone "better" exists - it's whether you’re looking for someone without flaws that eliminates the need for you to be an active participant in evaluating your life. Even in the right relationship, there’s no way to know for sure what life will bring. This is why relationships are always a risk - we have to do a cost benefit analysis and decide what’s best for us.
How to actually decide
So how do you move from endless analysis to actual decision-making? You create structure around your choices. Instead of leaving the decision open-ended (which invites endless second-guessing), give yourself a specific decision point.
Try this: "I will continue seeing him for one more week, and on Sunday, I'm going to decide yes or no." Then, when Sunday comes, you make the decision based on what you know right now, not on what you might discover if you keep dating for another six months.
Once you make that decision, here's the crucial part: you decide you're sure. You choose to believe you made the right call. You stop looking for escape hatches and start investing in the relationship you've chosen to be in. You enjoy being with this person that you've decided to be with.
This approach works because it eliminates the mental energy drain of constantly re-evaluating your choice. Instead of spending your emotional resources on "should I stay or should I go," you can channel that energy into actually building something meaningful with your partner.
Frequently Asked Questions
What if I choose him and he hurts me later? I can’t handle another heartbreak.
It will suck. It will be really hard. But let me tell you the documented cases of dying from heartbreak are very rare. (To be scientifically accurate, Broken Heart Syndrome is a recognized condition where your heart responds to extreme stress, like loss of a partner, and mimics a heart attack because of the stress. And even in critically ill patients, like grandparents with heart disease, most recover.)
Now I know you weren’t actually thinking you’d die if you’d experience another heartbreak but I give that extreme example to ground us in what we’re talking about here.
Heartbreak is painful. But you can handle it. You might get sad, you might need support, but you’ll get through it. But in this moment, when you are scared of the potential heartbreak, searching for a way to “be sure” is probably coming from a place of you searching for certainty, for a 100% guarantee. And I have to remind you that an 100% guarantee of anything when it comes to love doesn’t exist.
Can you accept that there’s no way to 100% prevent yourself from experiencing pain in a relationship? From getting hurt? Of him deciding to leave after 20 years of happy marriage? Of him getting tragically hit by a bus in 5 years?
If you need 100% certainty that you won’t experience pain in a relationship, then I’m afraid your only option is not to get into a relationship.
What if I make the wrong choice and miss out on someone better?
Here's the thing - there's no such thing as "the one" perfect person for you. There are many people you could build a happy life with. The fear of missing out on someone "better" will keep you single forever if you let it. Focus on whether the person you're with makes you happy and meets your core needs, not on hypothetical alternatives.
What if I choose to commit and then realize I made a mistake?
Relationships aren't prison sentences. If you discover fundamental incompatibilities or your partner treats you poorly, you can always leave.
A wrong answer is better than no answer.
We are cultured to beat ourselves up when we make mistakes. Whether it was through the culture of school when we were young, rewarding us for A grades and perfect attendance or the wiring of our brains that makes us remember bad things with 10x stronger associations than good things, it’s really natural that we’ve demonized mistakes.
But mistakes are actually a huge part of our successes. Michael Jordan is commonly quoted as saying: “I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”
One of the all-time greats in sports made plenty of mistakes. The higher stakes get, the more likely is that you will have made mistakes along the way. And in relationship terms, these “mistakes” may not be a bunch of failed relationships or rejections. They may be situations where you judged a situation wrong, where you gave somebody bandwidth that they took advantage of or when you asked someone for something and let it slide when they didn’t give it to you.
But every step in every relationship is an opportunity for us to learn, so let’s reframe making the wrong decision.
Yes, you may end up having had spent more time with this person than would be ideal if you decide to commit and it doesn’t work out. But there is value in that time, first, and secondly, at whatever point you get clear that it’s a “no” for you, you’ll have a clear answer, rather than your confusion right now.
Now this isn’t to say that you should definitely move forward with this person, but release the pressure that you’re currently feeling to be right. Consider the situation, make a decision and then really earnestly give it a try. If it works, amazing! If it doesn’t, at least you’ll have a clear answer.
How do I know if I'm settling or just being realistic?
Settling means staying with someone who doesn't meet your fundamental needs or because you aren’t sure you can find anything better. When it comes to “being realistic,” this phrase is often low self-worth masquerading as a helpful insight. If “being realistic” makes you tell yourself that your expectations are too high or that what you want isn’t possible, then we’d challenge you that you’re not being “realistic” because there are tons of people out there who find partners that make them feel so lucky and that meet everything they wanted for.
Does that mean that the right relationship will be with someone who is perfect? No, there will be flaws or imperfections in every human, but the idea is that the imperfections in the person who you choose to be with, probably won’t be ones that matter that much to you. On the other hand, if you are talking yourself into being okay with things that you’re fundamentally not okay with, this is probably settling and it’s time to address what makes you feel like you can’t have what you want.
What if my friends and family don't think he's right for me?
Listen to their concerns, especially if multiple people are raising similar red flags. Especially if those flags have to do with you compromising on your own dreams or how they feel like you seem to be feeling from their perspective. But on the other hand, you're the one who lives with this decision. If they are seeing external mismatches but you feel really solid in how you feel in the relationship, then it might be their own fears or preferences being projected onto your relationship. Trust your own judgment while staying open to genuine concerns about your wellbeing.
How long should I date someone before making a commitment decision?
There's no magic timeline. At each stage of the relationship, you can move as fast or as slow as you feel comfortable. Some general guidance though: if you have been going on dates for a month, it’s likely that you have enough information to see if you might be willing to be in a relationship. For longer term commitments like moving in together or marriage, we like to say that it’s important to have gone through some hard times - either in one or both of y’alls lives before you make those sort of decisions.
The paradox of modern dating is that having more freedom has made us less certain about everything, especially something as significant as choosing a life partner. But certainty isn't something you find - it's something you create. It's a choice you make to stop sampling all the jams and commit to the apricot you actually like.
Being “sure” will not just happen to you, rather it comes from you having give yourself a frame of mind in how you’re thinking about the person and enough time to collect information and going from there.
The most successful relationships aren't built on finding the perfect person; they're built on two imperfect people choosing each other and then doing the work to build something beautiful together. So give yourself permission to choose. And then give yourself permission to enjoy the relationship you've decided to invest in.
