How to Decide If You Should Keep Dating Someone
Estimated reading time: 8 minutes
Dating involves a series of decisions. Some are minor and straightforward, others are complicated and emotion-laden.
Should I go on another date?
Do I like this person, or do I just like being liked?
Should I keep trying? Or cut my losses?
While there isn’t a decision tree for dating, there is a pattern to the types of decisions we face and the ways we get stuck.
Let’s walk through the arc of dating and three key decision points.
The Early Days: Should You See Them Again?
A low-pressure first date — a good chance to gather information and see how you feel.
You matched, you flirted, you made it to the first date.
At this stage, you don’t need to consult a detailed pros and cons list. Nor do you necessarily need to predict long-term compatibility or assess shared values.
For the first few dates, one of the best questions to ask yourself is a simple one:
“Do I want to see them again?”
Many people get stuck here because they either focus on:
How the other person looks on paper, or
Whether they felt a spark
Both are problematic.
The first ignores how you feel. When you focus more on the idea of someone than to how your actual experience with them — and those don’t match — you may feel cognitive dissonance, a mental discomfort from holding contradictory beliefs, feelings, or thoughts.
You might like things about the person: they’re attractive, nice, have similar interests, and gainfully employed.
But do you actually like being with them? Do you enjoy their company? Do you want to see them again?
The second mistake conflates feeling a spark with compatibility. A spark feels exciting, but it’s not a reliable indicator of how someone treats you or whether your values align.
Neither of these tendencies account for more meaningful signals, like respect, ease, curiosity, or emotional presence.
So whichever one is your tendency: take it one date at a time.
Your goal during this phase is to gather information iteratively, not to make a lifelong commitment.
Want help identifying red flags, green flags, and early gut checks? Read Noticing the Signs, a guide to what actually matters when you're getting to know someone new.
The Middle Phase: Is This Going Anywhere?
When things are going well, it’s still fair to ask,“Where is this going"?”
After a number of good dates (let’s say five or more), another question comes up:
“Where is this going?”
This can be a tricky question to answer because you likely have a few different goals:
Having fun
Feeling emotionally connected
Determining long-term potential
Some people focus on the fun goal too long and avoid more serious conversations.
Some conflate limerence, “new relationship energy”, or honeymoon period with a genuine emotional connection.
Some start dreaming about getting engaged and married before they’ve spent enough time getting to know the person well..
Anyone can make a great first impression. But how do they handle:
Making plans?
Following through?
Communicating clearly?
Navigating disagreements?
In this phase, paying attention to patterns is important. Basically, past and existing behaviors will tell you a lot more about compatibility than words and future potential.
Make sure that while you're enjoying yourself, you're also observing whether the qualities and values that matter most to you (such as kindness or ambition) are appearing consistently.
Many people speed through the middle phase of dating — excited by momentum, eager for certainty. But rushing can lead to mistakes, missed signals, or a shaky foundation.
Read more: In Go Slow to Go Fast, I explore how acting with intention — instead of urgency — leads to better outcomes in dating, work, and life.
Defining the Relationship: Is It Time to Be Exclusive?
Exclusivity can be exciting or unclear. The key is mutual clarity, not assumptions.
So it’s been ten dates, a few months, or possibly a year.
Exclusivity can be exciting or scary (or both).
Maybe things are going well. Maybe you’re sleeping together. Maybe you’ve talked about future vacations and meeting each other’s family.
Maybe you or they have dropped hints about commitment.
But nothing’s been defined.
Unfortunately, exclusivity should not be an assumption. It requires a mutual decision.
One person might be thinking, “We’re basically together-together.”
The other might be thinking, “I like them… but I’m not ready for an explicit commitment or label.”
Before bringing up the conversation, answer for yourself:
Are we emotionally available for each other? (See Emotional Alignment)
Are our values and goals aligned?
What conversations haven’t we had yet?
Read more: The Gottmans’ Eight Dates provides a deeper dive into these conversations.
Why People Get Stuck
A lot of people ignore their needs, delay decisions, or rush to define something for understandable reasons:
Scarcity: “This might be the best I’ll get.”
Status: “At least I can say I’m dating someone.”
Comfort: “Some of my needs are met, and that feels better than starting over.”
Hope: “Maybe they’ll change.”
Avoidance: “It’s not that bad.”
The problem is that each of these feels reasonable in the moment, but may not actually be helpful long term.
If you stay in something unclear or misaligned for too long, it can lead to deeper attachment, wasted time, and resentment.
Read more: How overthinking impacts your dating decisions and leaves you more stuck.
What Helps You Decide
Some decisions aren’t obvious. Which path you choose depends on what you’re willing to live with.
When the answer isn’t obvious, try asking:
“Is this something I can accept and live without?”
Rather than deciding whether someone is good or bad, you’re evaluating whether the dynamic works for you.
If they’re fun, but flaky, can you accept that?
If they’re kind and stable, but emotionally reserved, can you live with that?
A Quick Reality Check
I wish I could give you a magic formula.
If you’re looking for a guaranteed outcome, a script to follow, or a checklist that tells you exactly what to do, this article probably won’t feel satisfying.
Dating decisions are rarely that clean. They’re influenced by timing, patterns, emotions, fears, hopes, and personal values — often all at once.
And if you’re feeling burnt out, even the clearest advice can feel overwhelming or irrelevant.
You won’t always know whether you made the right decision. But you can try to make the best decision you can — one that’s thoughtful, informed, and informed by your boundaries and needs.
Final Thoughts
Dating is a process of learning about yourself, about others, and about what makes connection worth continuing.
You don’t need to know the end from the start. But you do need to ask better questions along the way. Those questions won’t give you guarantees, but they will help you stop outsourcing clarity and decision-making to the other person.
Let your early dates be light and curious.
Let your mid-stage relationships be honest and observant.
Let your biggest decisions reflect your needs, not your fears.
