Are You Overthinking or Anxiously Waiting?
🕒 Estimated reading time: 6 minutes
Disclaimer: This post is for informational and reflective purposes only. It is not intended to diagnose, treat, or replace advice from a licensed mental health professional. If you’re struggling with attachment issues or relationship challenges, consider reaching out to a therapist or counselor for personalized support.
Stuck in your head, overthinking a text, or wondering what that look meant?
Does dating ever leave you spiraling — stuck in your head, overthinking a text, or wondering what that look meant?
Whether you're dating online or meeting people in real life, it’s easy to get caught in a mental loop: replaying moments, filling in blanks with assumptions, and waiting for signs that someone likes you back.
Sometimes that anxiety gets called “anxious attachment,” but you don’t need to identify with that label for it to feel familiar. At some point, most people experience fear, doubt, or confusion that quietly (or not so quietly) shapes their choices. Left unchecked, it can lead to behaviors that work against the very connection you're hoping to build.
This article breaks down common signs of overthinking in five everyday dating scenarios — and offers ways to pause, reflect, and respond more intentionally.
1. Initiating Interest
Examples: Approaching, expressing attraction, or asking someone out
This is where many people hesitate, worry, or back out entirely.
You might be:
Nervous about approaching someone in public — “What if they’re taken? What if I’m reading this all wrong?”
Debating for days about whether to text someone after meeting at a party
Overanalyzing if it’s too much to ask them out, or too soon to seem interested
What to try instead:
Before deciding what to do, notice what’s happening inside of you.
Is the hesitation based on fear? Assumptions? A desire to control the outcome?
You don’t need certainty to act, just enough self-trust to try something challenging.
Ask yourself: “Would I regret not doing this?” If the answer is yes, consider making the move, gently and respectfully. Curiosity is often more effective than strategy.
Lastly, it’s common to freeze up, especially if you’re worried about rejection or awkwardness. You might find How to Break the Ice (Offline) helpful for practical tips on getting started in person.
2. Early Interactions
Examples: First dates, early-stage connection, pacing
After the initial match, meetup, or exchange, the mind loves to jump ahead. You might be:
Over-preparing for a first date to avoid being “too much” or “not enough”
Putting pressure on yourself to prove you're worth seeing again
Rushing to lock in plans to calm the discomfort of not knowing where things stand
What to try instead:
Treat each interaction as information gathering, rather than a test or an audition. Remember: you’re exploring compatibility.
Are you trying to control the pacing because you're afraid whatever you’re excited about might disappear?
If you are, then let curiosity set the tone, not urgency.
When you catch yourself over-preparing or trying too hard to “win” the date, it can help to tune into green and red flags instead. I break that down in Noticing the Signs: Green Flags, Red Flags, and Gut Checks.
3. Communication
When every “...” feels like a cliffhanger.
Examples: Texting before or after dates, or between seeing each other
This one gets everyone. You might find yourself:
Re-reading texts, trying to decode tone or intent
Wondering if a slow reply means they’ve lost interest
Crafting the “perfect” message, then deleting and rewriting it five times
Asking friends to weigh in (“Should I wait to respond? Was that too forward?”)
What to try instead:
Zoom out. Then ask yourself: “What story am I telling myself right now?”
Is it: “They don’t like me” or “I messed it up”?
Is that based on evidence, or is it a fear talking?
What would you normally say if it were a friend or family member you felt comfortable with? Try responding with that version of you.
Lastly, not everything requires a strategy — sometimes a light, thoughtful reply is enough.
4. Uncertainty & Labels
Feeling lost in a sea of “what are we?”
Examples: Waiting for clarity, exclusivity talks, “what are we?” moments
Here’s where anxious overthinking can lead to paralysis or premature DTR talks.
You might be:
Interpreting every interaction as a sign of where things are going
Hoping they’ll bring up exclusivity so you don’t have to
Avoiding the conversation entirely, even if you’re feeling anxious or unsettled
What to try instead:
Get clear on your timeline and needs before involving someone else. Do you want clarity, or do you just want reassurance?
It’s okay to ask for clarity — but consider your intention. Is it to connect, or to calm your own panic? If it’s both, name that honestly. Try: “I’ve been enjoying getting to know you, and I’m wondering how you're feeling about this so far.”
5. Online Dating Habits
When swiping turns into spiraling.
Examples: Profiles, photos, matching, messaging
Dating apps can be their own anxiety vortex. You might notice yourself:
Writing overly detailed bios to “prove” you’re interesting
Choosing performative photos to seem more impressive
Swiping on almost everyone to maximize chances of being “chosen”
Overthinking every message or spiraling when replies slow down
Rushing to meet in person to validate the connection
What to try instead:
Go for simplicity. Use photos and bios that reflect your current life — not the curated highlight reel.
Swipe intentionally, and remember: someone else’s delayed reply doesn’t define your worth.
Focus less on being “liked” and more on being seen — for who you actually are.
Check out this primer on Online Dating — in it, you’ll whether you should try it, and how to make it a productive experience.
The Bottom Line
Overthinking is a natural response to uncertainty. But it’s often the stories we tell ourselves — not the reality of what’s happening — that create the most distress.
The next time you feel anxious or stuck, try asking yourself:
“Is my action driven by fear, or by a desire to connect?”
That one question can help shift you out of panic and into perspective.
You don’t have to eliminate fear or uncertainty to date well. You just need enough self-awareness to spot your patterns — and enough courage to interrupt them.
My article on emotional awareness digs into how noticing your stories and patterns is the foundation of dating with clarity. If you want a guided self-check you can bring into each interaction, start there.
And be sure to check out these articles on how to address burnt out and disillusionment.
Book Recommendations
Want to understand your dating patterns more deeply? Here are two books worth checking out:
Attached by Amir Levine and Rachel Heller — Learn about the role of attachment styles in adult relationships.
How to Avoid Falling in Love with a Jerk by John Van Epp — A practical guide about pacing, compatibility, and long-term decision-making.
