The Dating Advice No One Talks About
Dating can become frustrating when you keep meeting people, giving relationships a chance, and hoping that this time things will work out, only to discover that you and the other person want different things. You may have chemistry, enjoy each other’s company, and genuinely look forward to spending time together. But somewhere along the way, you realize that the relationship you’re building may not be the relationship you want.
So you start over. You meet someone new, try again, and hope for a different experience.
Meanwhile, you’re consuming dating advice from social media, listening to relationship experts, and reading articles about what to do and what to avoid when looking for love. With so much information available, you might expect finding a lasting relationship to feel a little easier.
Yet here you are, still trying to figure it out.
Maybe you’ve wondered why meeting someone you like seems to be the easy part, but finding someone with whom you can build a future feels so much more difficult. Maybe you’re tired of getting excited about someone, allowing yourself to imagine what the relationship could become, and then discovering that things aren’t going to work out the way you hoped.
You want dating to lead somewhere.
You want to look at the person beside you and feel grateful that the two of you found each other.
That’s what you’re hoping for when you put yourself out there and give dating another chance. You want to find love that lasts.
This is the dating advice you won’t discover scrolling through social media. It’s a different perspective that no one talks about.
Part One: Why Does Dating Feel So Hard?
The Excitement of Meeting Someone New
It starts with attraction. Two people notice each other, like what they see, and decide to go on a date. The date goes well, so they go out again. They enjoy each other’s company, the texts keep coming, and before long, they’re spending a lot of time together. It feels good. And sometimes, that’s where the trouble begins.
How Dating Can Become Difficult Even When Things Start Well
Not every relationship falls apart because somebody cheats, lies, or treats the other person badly. Sometimes, two people can love each other, enjoy being together, and treat each other well, yet still want completely different things out of life.
Imagine spending three years with someone, believing you’re building toward the same future, only to discover that you have very different ideas about what that future should look like. What happens then? Does one person give up something they’ve always wanted? Does the other agree to a life they never wanted for themselves? These aren’t small differences that can always be worked out with a little compromise.
And the longer two people spend building a relationship under the assumption that they want the same things, the harder it can be to face the fact that they don’t.
That’s why conversations about what matters most need to happen early in dating, ideally within the first 30 days. Not because two people need to have their entire future figured out in a month, but because they need to start learning whether they’re heading in the same direction before becoming deeply attached.
Talking Often Doesn’t Necessarily Mean Discovering What Matters
Some couples talk every single day. They text from morning until night, call each other after work, spend weekends together, and always have something to talk about.
They know each other’s favorite foods, the shows they watch, what makes them laugh, and how they like to spend their free time.
But knowing someone’s routine isn’t the same as knowing what they want out of life.
Two people can spend a year dating and still have very different ideas about marriage, family, money, and the future. They can have a great time together without ever realizing that they’re heading in different directions.
And because things feel good, there may be no obvious reason to question where the relationship is going until something happens that makes those differences impossible to ignore.
Chemistry, Attachment, Connection, and Compatibility
Chemistry can be powerful. Physical attraction, flirting, and playful banter can make two people eager to spend time together. The excitement builds, feelings develop, and before long, they may find themselves deeply attached.
But chemistry doesn’t tell two people whether they’re compatible. And when attachment is mistaken for genuine connection, that misunderstanding can lead to heartache.
Compatibility is what allows two people to build a connection. It’s about discovering who someone really is, what matters to them, what they want out of life, and whether those things align with what’s important to the other person.
The challenge is that chemistry can be so captivating that the questions that reveal compatibility get pushed aside. When the dates are fun, the attraction is strong, and the relationship feels good, it’s easy to assume that everything else will fall into place.
That’s why asking the right questions early matters. It gives two people the opportunity to discover things about one another that lead to connection, not simply attachment.
Consider ambition.
An ambitious man or woman may work long hours, devote significant energy to a career, or spend years building a business. Their partner might wonder why work seems to take up so much of their time or why they aren’t more available.
But there’s often a deeper reason behind that ambition. Perhaps they grew up without much money and are determined to create financial security. Maybe they watched their family struggle and want to build a different life for themselves and their future children. Or perhaps they have a dream they’re committed to pursuing and understand that reaching their goals will require time, discipline, and sacrifice.
Understanding what drives someone can change how their partner sees their ambition. Instead of interpreting long hours as a sign that the relationship doesn’t matter, they may recognize what their partner is working toward and become more supportive, especially during demanding seasons.
But understanding why someone is ambitious doesn’t automatically mean being compatible with them.
Compatibility means understanding what that person’s lifestyle looks like and being comfortable with the time they can realistically offer. It means not entering the relationship expecting them to work less, change their priorities, or become more available simply because the relationship progresses.
Of course, two people can discuss their needs and find arrangements that work for both of them. The important thing is that those arrangements are acceptable to both, rather than one person entering the relationship counting on the other to become someone different.
The same is true when it comes to family.
One person may feel that family should always be an essential part of life. They enjoy spending time with relatives, want to remain close to their parents and siblings, and imagine raising children in a family where everyone stays connected. The person they’re dating may value family, too, but prefer more independence and less involvement in one another’s everyday lives.
Understanding what family means to each person can help them appreciate why they see things differently. But compatibility requires more than understanding. They also need to determine whether their expectations for family closeness, boundaries, and involvement can work together.
If one person wants family to play a major role in everyday life and the other prefers considerably more distance, they need to be honest about whether they’re comfortable with the life that would create. Compatibility means being able to agree on an arrangement that works for both of them, not assuming one person will eventually adopt the other’s preferences.
Travel is another example.
Two people might both love traveling. They plan vacations, explore new places, and make wonderful memories together. But one dreams of spending months abroad and experiencing different cultures, while the other wants to settle close to family and take occasional vacations. They share an interest, but their visions for the life they want may be very different.
Understanding those differences helps them see what each person wants from life. Compatibility means determining whether they can build a lifestyle that satisfies both of them.
Two people might also agree that they want children but have very different ideas about raising them.
One imagines raising children who grow up to become independent adults, move wherever life takes them, and build lives of their own. The other envisions a close-knit family that stays connected across generations, perhaps even living near one another as the children grow older. They may also have different expectations about parenting responsibilities, discipline, education, and the kind of home they want to create.
Wanting children is one thing. Understanding what having a family means to each person is another. These conversations help reveal whether two people share a vision for the family they want to build and whether they’re comfortable with the expectations that come with it.
In each of these situations, understanding helps two people see beyond what they observe on the surface. It gives them a clear picture of the experiences, values, priorities, and motivations that shape the person they’re dating. But compatibility requires them to go a step further and determine whether they can accept those differences and build a life that works for both of them.
This is how compatibility builds the bridge to genuine connection, creating the foundation for a love that lasts.
Part Two: What Are You Really Looking For?
Let’s talk about what you’re looking for in a partner.
You probably have a good idea of the kind of person you’re attracted to and the qualities you’d like them to have. But when you’re thinking about spending your life with someone, there are a few things worth looking at a little closer.
Let’s start with physical attraction, because yes, it matters. You should be attracted to the person you’re dating. But there’s more to choosing a partner than finding someone you think is good-looking. Character matters, too, and so do the things that affect your everyday life together.
Be Honest About What Attracts You
Maybe you have a type, or maybe the people you’re attracted to look very different from one another. Whatever your preferences are, acknowledge them. If physical attraction is important to you, own that. You’re allowed to have preferences when it comes to the person you want to date.
As you get to know someone, give yourself time to discover who that person is beyond what first caught your attention.
Look Beyond the Pretty or Handsome Face
A pretty or handsome face can get someone’s attention, but character is what deserves a closer look when considering a long-term partner.
Think about the qualities that matter in a relationship. Honesty, integrity, loyalty, kindness, and accountability are good places to start.
These qualities are easy to name, but recognizing them in someone’s behavior takes time.
An honest person tells the truth, even when it’s uncomfortable. Someone with integrity follows through on their word and takes responsibility for their actions. A loyal partner respects the commitments they’ve made. And someone who is accountable can acknowledge a mistake without making everyone else responsible for it.
These qualities become clearer through everyday interactions. Notice how someone treats people when there’s nothing to gain. Pay attention to how they respond when you disagree, when plans change, or when something doesn’t go their way. Can they communicate respectfully? Can they admit when they’re wrong? Do their actions line up with what they’ve told you?
A few good dates may reveal that two people enjoy each other’s company, but learning someone’s character requires seeing how they handle different situations over time.
These qualities also need to exist on both sides. A relationship built on honesty, loyalty, and integrity requires both people to bring those qualities into the partnership.
Choosing a long-term partner means choosing someone to trust, communicate with, and work through life’s challenges alongside. Character deserves just as much attention as the qualities that initially create attraction.
Money Is About More Than Who Pays
Money can reveal a great deal about what two people expect from a relationship. One person may believe a man should provide for his family. Another may expect couples to split expenses equally. There are so many ways couples can handle their finances.
There isn’t one financial arrangement that works for every couple. What matters is whether both people understand the arrangement, agree to it, and are prepared for the responsibilities that come with it.
Beyond deciding who pays, there’s another important consideration: whether both people are capable of carrying the household if circumstances change.
Can You Hold Things Together if Life Challenges You To?
Imagine a couple where one partner earns significantly more than the other. They build their lifestyle around that income, and everything is going well. One partner pays most or all of the bills, while the other works part-time, stays home with the children, or earns a smaller income.
Then something changes.
The higher earner loses their job. Their business struggles. An illness or injury prevents them from working for a while. Suddenly, the income they’ve depended on is no longer there.
What happens next?
They may need to cut back on spending, find another source of income, or move into a smaller home. Their life may look different for a while, but they can figure out the next steps together.
This is where each person’s capability and willingness become important.
Can the other partner step in and earn an income if that’s what the household needs? Can they manage the bills, make financial decisions, and adjust to a tighter budget? Are they willing and prepared to take over responsibilities they didn’t previously have?
This is something to think about before building a life together. If one person loses their income or becomes too sick to manage the household, the other person needs to be ready to take over. There may not be time to go back to school, earn a new degree, or spend years developing the skills needed to support the family. The preparation needs to begin before it’s needed.
That doesn’t mean both people must have the same earning potential. One person may be capable of earning a substantial income, while the other may be able to earn considerably less. What matters is understanding what each person could realistically manage alone and what that would mean for their shared lifestyle.
If one partner can carry the household on a $100,000 income and the other could manage only on $30,000, the couple needs to understand what life would look like on that lower income. Could they afford their home? What expenses would have to go? What changes would they need to make to keep the household running?
These aren’t questions to wait until a crisis to answer. They’re part of understanding the life two people are choosing to build together.
When choosing a partner, consider not only the life you can build with that person, but also the life each of you could sustain if the other were suddenly unable to carry their share of the responsibilities.
Financial strain can affect far more than a person’s bank account. It can affect their sense of security, emotional well-being, physical health, and relationships.
A 2022 study examining suicide deaths in the United States from 2017 through 2019 found that job loss, financial strain, or housing problems were identified as contributing circumstances in 22% of male suicide deaths among adults ages 45 to 64. For women in the same age group, those circumstances were identified in 15.1% of suicide deaths.
You can find this study by searching “Job Loss, Financial Strain, and Housing Problems as Suicide Precipitants: Associations With Other Life Stressors,” published in 2022 in SSM – Population Health.
These figures describe circumstances identified among people who died by suicide, not the percentage of all men or women who experience financial difficulties. The study also does not establish that financial strain alone causes suicide. However, it highlights how financial and housing problems can be part of the broader challenges people face.
When a household depends heavily on one person’s income, that person may feel enormous pressure to keep everything going. Having a partner who is both willing and capable of carrying the household when necessary gives the couple more options when something unexpected happens.
Are You an Asset or a Liability?
It’s easy to focus on what a potential partner can bring into a relationship, but the same consideration applies to the person doing the choosing.
Am I an asset or a liability to the relationship I’m entering?
A person who expects ongoing support but has neither the willingness nor the readiness to take responsibility if needed may leave their partner carrying more than they can comfortably manage.
This is what makes someone a liability.
Capability Has No Gender
The ability to carry a household isn’t just about earning money. It’s also about being able to manage the responsibilities that keep everyday life moving.
Cooking, cleaning, caring for children, managing appointments, handling bills, making decisions, and keeping a home running are all part of building a life together. These responsibilities don’t automatically belong to one person because of their gender.
If the person who usually cooks becomes ill, can their partner prepare meals? If the person who manages the bills is suddenly unavailable, can the other person find the information they need and keep payments on track? If the parent who usually handles school pickups can’t do it, can the other parent step in?
These situations may sound ordinary, but they’re part of real life. People get sick. Work schedules change. Family members need care. Unexpected responsibilities show up without asking whether the timing is convenient.
A partner doesn’t have to perform every task equally well or prefer doing everything the other person does. But being willing to learn and capable of taking responsibility makes a difference when the usual arrangement no longer works.
This also applies to leadership and decision-making. If one person normally takes the lead, the other should still be able to make important decisions when necessary. A household shouldn’t come to a standstill because one person is temporarily unable to manage it.
Think about the roles you and a potential partner expect to take on. Are those roles based on genuine agreement, and could either of you adapt if life required a change?
The goal is to build a relationship in which both people are capable of handling life’s responsibilities, and prepared to take the lead when circumstances call for it.
Think About Health and the Years Ahead
When choosing a partner, it’s worth thinking about the kind of life you want to live together and how your everyday habits fit into that picture.
Health is part of that conversation. Consider how each of you approaches food, physical activity, sleep, preventive care, and the habits that support your well-being. You don’t have to make every choice the same way, but your approaches to health and daily living can affect the life you share.
For example, if being physically active is an important part of your life, it may be meaningful to have a partner who enjoys being active with you or supports your commitment to it. If you care about preparing meals at home, think about whether your partner’s habits and preferences fit comfortably with that lifestyle.
These conversations can also reveal what each person expects as they grow older. What does taking care of yourself mean to each of you? How do you feel about making changes to support your health? What kind of lifestyle do you hope to maintain in the years ahead?
It’s also important to recognize that health isn’t completely within anyone’s control. People can develop illnesses, experience injuries, or face health challenges despite their best efforts to care for themselves. A person’s health should never be treated as a guarantee of how long they’ll live or as a measure of their worth as a partner.
What matters is understanding how you each approach the things you can influence and how you would respond when life brings circumstances you can’t control.
A long-term relationship may include seasons when one person needs more care and support. Consider whether you can approach those seasons as partners, with compassion, flexibility, and a willingness to work through changes together.
You want someone whose values, habits, and approach to life’s challenges make sense alongside your own.
Choose Someone You Can Build With
By now, you can see that choosing a partner involves more than deciding whether you’re attracted to someone or enjoy spending time with them. It also means considering what life with that person might look like over the long term.
Think about the things that matter most to you. What kind of home do you want to build? What role will money play in your relationship? How do you want to divide responsibilities? What are your expectations around health, family, work, and the future?
You don’t need to agree on every detail from the beginning. Two people can have different preferences and still build a wonderful life together. What matters is whether you can talk honestly about those differences, reach agreements you can both live with, and adjust when circumstances change.
Pay attention to what you learn about a person over time. Listen to how they describe their goals, observe how they handle responsibilities, and notice whether their actions reflect what they say they want.
And remember to apply the same standards to yourself. Think about the kind of partner you want to be, the responsibilities you’re prepared to take on, and the areas where you may need to grow.
Part Three: Here’s What No One Is Telling You
Dating apps have made it easier to meet people. With a few swipes, you can discover people you might never have crossed paths with otherwise. You can learn a little about them, start a conversation, and decide whether you’d like to meet in person. For many people, this has become one of the primary ways to find a potential partner.
There’s plenty of advice about how to date online: how to choose the right pictures, write a good profile, send the right opening message, get more matches, and turn those matches into dates. People are learning how to get noticed, how to stand out, and how to make a good first impression.
There’s also plenty of advice about approaching someone in person. People learn how to make eye contact, start a conversation, show interest, and confidently ask for a phone number. Whether people meet online or in person, much of the advice focuses on making that initial connection.
But what should happen before you actually meet someone from an app or exchange phone numbers with someone you meet in person?
Here’s what no one is telling you.
The conversations that help you discover compatibility should happen before you become emotionally invested in someone.
Think about how dating usually unfolds online. Two people match, exchange messages, flirt, and begin learning little things about each other. They discuss their favorite foods. They talk about what shows they’re watching. They talk about what they like to do for fun. They talk every day, share funny videos, send good morning messages, and look forward to hearing from each other.
Before long, they’ve established a routine. They’re excited about the possibility of meeting. They may even begin imagining what a relationship could look like.
But how much do they really know about each other?
Now think about meeting someone in person. You notice someone you’re attracted to. They seem approachable, so you start a conversation—or they approach you. You exchange a few words, feel some chemistry, and consider exchanging phone numbers. But what if, before taking that next step, you took a moment to learn something about each other?
A spontaneous encounter doesn’t need to turn into an interview. Sometimes, a simple question is enough to get a conversation started. If you meet someone at the grocery store, you might ask, “What do you enjoy doing when you’re not out shopping for food?” If you meet someone at the gym, you might ask, “What do you like to do outside of working out?”
Their answer may spark your curiosity. You might discover that you share an interest, that they have an intriguing hobby, or that they enjoy something you’ve always wanted to try. Ask a follow-up question. Let the conversation develop naturally. You’re learning a little about the person beyond the setting where you met them.
The same questions about compatibility matter whether you meet online or in person. The difference is that an app gives you more room to explore those questions before deciding to meet. You can text, talk on the phone, and discuss the things that matter to you while you’re still deciding whether an in-person date makes sense.
When you meet someone in person, the conversation may need to unfold a little differently. You can start with something simple, follow your curiosity, and see where the conversation goes. But some things matter enough that you may want to know the answer before exchanging phone numbers.
Children are a good example. If you know you don’t want to date someone with young children, why wait until you’ve exchanged numbers and started communicating to find that out? Ask whether they have children. If their answer is yes, and the ages of their children matter to your decision, ask about that, too.
The same applies to other things you already know are important to you. If you have a clear preference or a dealbreaker that would determine whether you pursue a relationship, it makes sense to address it before investing more time.
Some people may not appreciate those questions. That’s their choice. But their reaction can also tell you something about how they approach communication and intentional dating. Someone may prefer not to share personal details with a stranger right away, but there’s a difference between wanting privacy and treating the very idea of having preferences or dealbreakers as a problem. You’re trying to learn whether there’s a reason to move forward, and they’re deciding the same thing about you.
Intentional dating means being honest with yourself about what you want, being willing to ask questions that matter, and allowing the answers to help you decide what comes next.
Imagine spending two months talking to someone every day. You’re attracted to each other, and you’re excited about where things might go. You become used to the daily communication and the possibility of a relationship.
This is how two people develop an unhealthy attachment instead of a genuine connection. Too much time is spent having conversations that don’t help them discover the things that truly matter.
Someone shows interest. They start sending good morning messages every day. They make the other person feel wanted, and that attention starts to mean something. Before long, feelings begin to develop, even though they know very little about the person’s character and values.
Instead of spending weeks learning someone’s favorite restaurant before learning what they want in a relationship, start with the conversations that help you understand who they are and how they live. Talk about the things that will matter if the two of you decide to build a life together.
You can learn about favorite foods, music, hobbies, and all the little things that make getting to know someone enjoyable along the way. Those conversations have their place, but they shouldn’t come before the ones that help you determine whether there’s a meaningful reason to keep moving forward.
Connect on the important things first, then enjoy discovering all the other things that make getting to know each other fun.
What Gives You a Reason to Fall in Love?
Imagine asking someone, “Tell me about a time when you had to make the choice to do the right thing, even when no one was watching.” Their answer can reveal something about their character. You may learn what guides their decisions, what they believe is right, and whether doing the right thing matters to them even when there’s no recognition or reward.
Imagine asking someone, “What values did your parents teach you that you still carry with you today?” Their answer can reveal what they believe matters in life and which lessons have stayed with them. You may discover that they value honesty, responsibility, respect, or keeping their word. You may also learn which values they want to carry into their own relationships and family.
Imagine asking someone, “What’s something you’ve done that scared you, but you knew you needed to do anyway?” Their answer can reveal courage. Courage isn’t always about doing something extraordinary. Sometimes, it’s having a difficult conversation, standing up for someone, admitting a mistake, or making a necessary change when staying where you are would be easier.
Imagine asking someone, “What’s one of the hardest experiences you’ve been through, and what did you learn about yourself from it?” Their answer can give you a glimpse into their resilience. You may learn how they’ve navigated difficult circumstances, what they’ve discovered about themselves along the way, and how those experiences have shaped the person they’ve become.
And imagine asking someone, “Tell me about a time when you went out of your way to help someone who couldn’t do anything for you in return.” Their answer can reveal kindness and compassion. You may learn about a time they showed up for someone who needed help, gave their time without expecting anything back, or recognized that someone needed support and chose to be there for them.
These are the kinds of conversations that allow you to discover qualities worth appreciating in another person. You’re learning about more than their interests, their accomplishments, or the things they enjoy doing. You’re getting to know what matters to them, what guides their decisions, and how they approach the situations life puts in front of them.
And those discoveries can change the way you see someone. You may find yourself admiring their honesty, respecting their determination, appreciating their compassion, or being drawn to the way they handle difficult situations. You’re developing an understanding of who they are, and that understanding gives you something meaningful on which to build a relationship.
Those are worthy reasons to care about somebody. Those are worthy reasons to fall in love.
And here’s what no one is telling you. These questions aren’t flirty. They aren’t sexy. They aren’t the typical questions dating experts tell you to ask. But if you want something to change, you have to be willing to try something different.
Discover the Questions That Reveal Compatibility
Knowing what you want in a relationship makes a difference in how you date. When you’ve taken the time to think about your values, expectations, goals, needs, desires, priorities, and dealbreakers, you have a clearer picture of what you’re looking for.
That clarity helps when you meet someone new. Rather than relying on attraction and chemistry alone to determine whether a relationship has potential, you can have conversations that help you discover whether you’re compatible.
Here are five questions to get you started.
1. What does being in a committed relationship mean to you?
You want to understand what commitment looks like to this person. Are they thinking about building a life with someone, showing up consistently, and working together toward a shared future? Their answer gives you a better idea of what they’re looking for and whether it aligns with what you want.
2. Are you dating with the intention of finding a long-term partner, or are you looking for something more casual?
This question helps you understand why someone is dating in the first place. If you’re looking for a life partner and they’re just looking to have fun, it’s good to know that before either of you develops feelings. You can enjoy someone’s company and still want two completely different things.
3. What are your career goals, and what are you working toward professionally?
Someone’s career goals can tell you a lot about their ambition and what they’re working toward. They may be pursuing advancement, building a business, or continuing to learn and grow in a field they enjoy. Their answers can also give you a glimpse into their potential earning capacity and financial future.
4. What does a healthy relationship look like to you, and what do you believe each person contributes to it?
This question gives you an opportunity to hear what someone expects from a relationship and what they believe they’re responsible for bringing to it. You may discover that you both value communication, affection, support, and putting in the effort to make a relationship work. Or you may discover that you have very different ideas about what being a partner means.
5. What kind of life do you want to build over the next one to three years, and what role do you envision a partner playing in that life?
Where someone sees themselves in the next few years can tell you a lot about whether your lives are heading in a similar direction. Maybe they’re building a business, planning to relocate, or working toward a major personal goal. How they see a partner fitting into those plans matters, too. You’re getting a sense of whether the lives you each want to build have room for one another.
These five questions are a starting point. The questions that matter most to you will depend on what you’ve identified as important in your own life and the kind of relationship you want to build. When you understand your own answers, you have a clearer sense of what compatibility looks like to you.
If you’d like more questions to explore, Tonight’s Connection is a FREE useful resource. The app has 47 categories and more than 2,000 questions designed to help you get to know someone better through meaningful conversations. You can explore the categories and answer questions for yourself first. Then, when you’re getting to know the other person, ask those same questions to see how their answers compare with yours.
This is how you recognize compatibility. You may discover that you agree on the things that matter most, or you may find differences worth discussing. Either way, you’re learning more about each other and gaining a better understanding of whether you’re compatible.
Compatibility means understanding where you align, recognizing where you differ, and determining whether those differences work for the kind of relationship you both want. The right conversations can help you discover whether you have the foundation to build something meaningful.
This is the dating advice nobody talks about. If you want to find love that lasts, this is how you do it. The way we’re traditionally taught to date leads people to develop unhealthy attachments instead of real connections built on compatibility.
Think about it this way: you can attach an Android phone to an iPhone charger, but because the two aren’t compatible, they don’t connect. Because there’s no connection, the phone doesn’t function properly. That’s also what happens in relationships. When people are attached instead of connected, the relationship won’t function properly either.
Tonight’s Connection
To discover more FREE questions that help you determine compatibility, check out the Tonight’s Connection app. The Conversation Starters app, helping couples and singles grow closer through meaningful conversations.