How to Date Without Constantly Questioning Your Feelings

You meet someone you like.

The first few dates go well. There’s attraction, conversation flows, you’re enjoying yourself. And then it starts. The questioning. The analyzing. The constant internal interrogation about whether what you’re feeling is real or enough or right.

Do I actually like them or am I just lonely? Is this excitement or anxiety? Should I feel more by now? Why don’t I want to text them constantly like I did with my ex? Is the fact that I’m not obsessing about them a red flag? Or is the fact that I’m questioning everything the actual red flag?

You can’t just be in the experience. 

You’re constantly pulling yourself out of it to evaluate it, to make sure you’re feeling the right things, to check if this is heading in the right direction. You’re dating someone but also dating your own overthinking brain that won’t let you just experience connection without dissecting it.

This is relationship anxiety, and it’s exhausting. 

It turns what should be an exploration into an interrogation. It makes you second-guess genuine connections because they don’t match some imaginary template of what falling for someone should feel like.

At Abri Psychotherapy, we work with people struggling with relationship anxiety all the time. 

The constant self-doubt, the need for certainty, the inability to trust your own feelings. It’s a particular kind of suffering that keeps you from actually being present in your dating life.

Today, let’s talk about why dating triggers so much relationship anxiety, how to tell the difference between anxiety and intuition, and how to stay present with your actual experience instead of constantly questioning it.

Why does dating trigger so much relationship anxiety?

Dating is uniquely designed to activate relationship anxiety because it combines uncertainty, vulnerability, and the possibility of rejection all at once.

When you’re dating someone new, you don’t have certainty about how they feel, where things are going, or whether this will work out. 

For people prone to relationship anxiety, that uncertainty is intolerable. Your brain tries to resolve the uncertainty by constantly analyzing, questioning, and seeking reassurance. But dating by its nature can’t provide the certainty you’re seeking, at least not immediately.

There’s also the vulnerability factor. 

Dating requires you to show yourself to someone and risk them not liking what they see. For people with relationship anxiety, this vulnerability feels dangerous. So your brain creates doubt as a protection mechanism. If you’re constantly questioning whether you even like them, you don’t have to fully risk being rejected by them. 

The questioning creates emotional distance that feels safer than genuine openness.

Relationship anxiety during dating often stems from past experiences. Maybe you’ve been hurt before and your nervous system is trying to protect you from hurt again. 

Maybe you had inconsistent caregiving growing up and you never learned to trust that connection is safe. Maybe you’ve internalized messages that you’re not worthy of love and now you can’t believe someone would genuinely want you. 

All of that creates relationship anxiety that makes dating feel threatening instead of exciting.

Cultural narratives about dating also feed relationship anxiety. You’re supposed to “know” when it’s right. You’re supposed to feel certain things at certain times. There are supposed to be signs and butterflies and clarity. 

When your actual experience doesn’t match those narratives, relationship anxiety tells you something must be wrong either with them or with you.

And modern dating culture, with its emphasis on having options and optimizing choices, makes relationship anxiety worse. 

You’re not just dating this person. You’re also wondering if there’s someone better out there. You’re comparing them to other matches. You’re trying to make the “right” choice like you’re selecting from a menu instead of getting to know a human being.

How can I stop constantly questioning my feelings while dating?

The constant questioning comes from a fundamental misunderstanding about how feelings work. 

You’re treating feelings like facts that should be immediately clear and consistent. But feelings, especially in early dating, are naturally fluctuating and ambiguous.

First, accept that uncertainty is normal in dating. 

You’re not supposed to know on date three whether you want to marry this person. You’re not supposed to have complete clarity about your feelings after a few weeks. The questioning itself isn’t a problem. 

The problem is believing that the uncertainty means something is wrong.

When you notice yourself questioning your feelings, pause and ask what you’re actually anxious about underneath the questioning. 

Are you afraid of making a mistake? Afraid of getting hurt? Afraid of hurting them? Afraid of missing out on someone better? The relationship anxiety usually isn’t really about whether you like them enough. It’s about deeper fears that the questioning is trying to manage.

Practice staying with your actual experience instead of analyzing it. 

When you’re with them, what do you notice? Do you enjoy their company? Do you feel comfortable? Are you curious about them? These present-moment observations are more reliable than your anxious thoughts about whether you feel the “right” way.

Stop comparing your feelings to some ideal template. 

Relationship anxiety loves to compare. You compare this connection to past relationships or to how you think you should feel based on movies or friends’ experiences. But your feelings don’t have to match anyone else’s pattern to be valid. You don’t have to feel butterflies or constant excitement or immediate certainty for the connection to be real and worth exploring.

Notice the difference between reflection and rumination. 

Reflection is productive. It’s checking in with yourself, noticing patterns, considering whether someone’s values align with yours. Rumination is relationship anxiety in action. It’s asking the same questions over and over without reaching conclusions. It’s circular thinking that increases anxiety rather than providing clarity. 

When you catch yourself ruminating, redirect to reflection or to being present.

And give yourself permission to not know yet. “I don’t know if this is going anywhere long-term” is a completely acceptable place to be in early dating. You can like someone and enjoy spending time with them without having figured out the entire trajectory of the relationship. 

The relationship anxiety wants certainty now. Reality is that certainty develops over time through experience, not through overthinking.

What’s the difference between relationship anxiety and intuition?

This is the question that torments people with relationship anxiety. When you have a negative feeling or doubt, how do you know if it’s relationship anxiety lying to you or genuine intuition telling you something important?

Intuition is quiet, clear, and grounded in your body. 

It’s a knowing that doesn’t need constant reinforcement. If your gut tells you someone isn’t right for you, that knowing is usually consistent and calm, even if it makes you sad. Intuition doesn’t waver. It doesn’t change based on whether they just texted you or how the last date went.

Relationship anxiety is loud, chaotic, and lives in your head. 

It asks the same questions repeatedly. It changes based on external factors. Yesterday you were sure you liked them, today you’re convinced you don’t, tomorrow you’ll probably swing back. That inconsistency is relationship anxiety, not intuition.

Intuition often has specific content. 

It might tell you “This person doesn’t respect my boundaries” or “We want fundamentally different things” or “I don’t feel safe being vulnerable with them.” These are concrete observations about the relationship dynamic. Relationship anxiety is usually vague. “Something feels off” or “I don’t feel how I’m supposed to feel” or “What if I’m making a mistake?” without being able to identify what specifically is wrong.

Check where the doubt is coming from. 

Does it arise in response to something specific they said or did? That might be intuition. Does it arise when things are going well, when you’re getting closer, when vulnerability increases? That’s more likely relationship anxiety activating because intimacy feels threatening.

Intuition doesn’t require you to constantly analyze it. It just is. 

You know it, you trust it, you act on it. Relationship anxiety requires constant checking. You ask friends what they think. You make pro and con lists. You search online for signs you’re with the right person. You’re desperately seeking external validation for what you’re feeling because relationship anxiety doesn’t trust itself.

And importantly, intuition is usually okay with whatever the truth is. 

If your intuition says this isn’t right, you might be sad but there’s acceptance underneath. Relationship anxiety is terrified of both outcomes. It’s scared of staying because what if it’s wrong, and scared of leaving because what if you’re making a mistake. 

That fear of both directions is relationship anxiety, not intuition.

How can I use RO DBT to stay present in dating without seeking constant reassurance?

Radically Open Dialectical Behavior Therapy (RO DBT) is particularly helpful for relationship anxiety because it addresses overcontrol, the tendency to be rigid, overly cautious, and disconnected from emotions and social connection.

RO DBT teaches radical openness, the ability to be vulnerable and receptive to new experiences and feedback even when uncertain. In dating, this means practicing being open to the experience without needing to control or predict the outcome. 

When relationship anxiety shows up telling you to question everything or protect yourself, radical openness means acknowledging the fear and choosing to stay present anyway.

One key RO DBT skill is “flexible mind.” 

This is the opposite of the rigid, all-or-nothing thinking that fuels relationship anxiety. Flexible mind recognizes that you can like someone and also have doubts. You can enjoy dating them and also feel scared sometimes. 

You can be uncertain about the future and still show up authentically in the present. 

Practice noticing when you’re in rigid thinking (“If I don’t feel completely certain, this must be wrong”) and consciously shifting to flexible thinking (“I can explore this connection even without certainty”).

RO DBT also emphasizes social signaling and learning from social feedback. 

When relationship anxiety has you constantly in your head questioning your feelings, you’re disconnected from actually attuning to the other person and the dynamic between you. Practice shifting attention outward. 

What are they communicating to you through their words and actions? What is the actual interaction like, not what your anxious thoughts say it should be like?

Self-enquiry is another RO DBT skill that helps with relationship anxiety. 

When you catch yourself seeking reassurance, pause and ask “What am I really needing right now? What am I afraid of?” Often the reassurance-seeking is trying to manage an underlying fear. Address the fear directly rather than trying to eliminate it through constant checking.

RO DBT teaches that emotions are important information, but they’re not facts. 

Your relationship anxiety might generate feelings of doubt, panic, or confusion. Those feelings are real, but they’re not necessarily accurate information about the relationship. Practice observing the feelings without immediately acting on them or taking them as truth. “I’m feeling anxious about whether I like them enough. That’s interesting. I don’t need to resolve that right now.”

And practice self-compassion, which is central to RO DBT. 

Relationship anxiety is suffering. It’s painful to constantly doubt yourself and your feelings. Instead of judging yourself for the anxiety or trying to force it away, can you acknowledge that this is hard? Can you treat yourself with kindness while you work on staying more present?

The goal isn’t to eliminate relationship anxiety entirely. 

It’s to develop the capacity to experience it without letting it run your dating life. You can feel anxious and still show up for dates. You can question your feelings and still choose to stay present with your experience. You can be uncertain and still be authentic.

Moving Forward with Less Anxiety

Dating with relationship anxiety is hard. 

You’re trying to connect with someone while your brain is constantly interrupting with doubts and questions and fears. You want to be present but you’re trapped in analysis.

At Abri Psychotherapy, we want you to know that relationship anxiety doesn’t mean you’re broken or incapable of connection. It means your nervous system learned somewhere along the way that connection is dangerous and uncertainty is intolerable. You can learn different patterns.

You can date without constant questioning. 

Not by forcing certainty or eliminating all doubt, but by developing tolerance for ambiguity. By trusting that you don’t need all the answers right now. By being willing to see where things go without needing to predict or control the outcome.

Your feelings don’t have to be perfectly clear to be valid. You don’t have to feel a certain way by a certain point. You’re allowed to be uncertain, to have mixed feelings, to not know yet.

The relationship anxiety will probably show up. But it doesn’t have to be in charge. You can notice it, acknowledge it, and choose to stay present anyway.

That’s how you date without constantly questioning your feelings. Not by eliminating the questions, but by recognizing that you can move forward even without all the answers.

Trust the process. Trust your capacity to learn about someone over time. Trust that if something isn’t right, you’ll know eventually without having to force the knowing now.

And most importantly, trust that you deserve to experience connection, even imperfect, uncertain, anxious connection, without having to have it all figured out first.

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