Dating Again This Spring? 4 Steps to Overcome Self-Sabotage Anxiety (Chicago, IL)
The weather is warming up, and you’ve told yourself that now is the time to get back out there to start dating.
You feel anxious about dating again after a breakup or divorce, especially if it’s been a while since you’ve gone on a first date with someone new. Or this might be your first time dating. Either way, you might feel a bit rusty when it comes to what to say, what to wear, and how to come across as cool and confident. Sometimes, that anxiety can show up as self-sabotage—overthinking, pulling back, or assuming it won’t work before it even begins.
It takes practice—and instead of trying to get it “right,” this blog will walk you through a few simple ways to ease back into dating. Think of this as building comfort step by step.
If you’re experiencing dating anxiety or noticing patterns of self-sabotage anxiety, you’re not alone. If you’re getting back into dating after a breakup or divorce, you might also notice familiar relationship patterns showing up again. I talk more about this in my blog on how working with an anxiety therapist in Chicago, IL can help you stop repeating the same relationship patterns.
Level 1: Start small with a simple compliment
If you tend to overthink when meeting someone new you find attractive, let’s start small. Take the pressure off of thinking, “OMG, this person is SO attractive. They’ll never talk to me,” or jumping into future-oriented relationships, “What if we start dating?”
Slow down. Take a breath.
I like to tell my clients who are going back into the dating pool to imagine it’s similar to applying for a job. You’re going to get rejected a lot, but the few interviews you do get are a chance to practice what you’ll say, what to wear so you feel comfortable and confident, and whether your values are compatible.
Exercise: Start with a low-stakes conversation with at least one person you meet in your daily life.
Example script: “Hi, I wanted to tell you that I really liked your shirt! Hope you have a great day!” and then keep on walking. No need to stop and have a conversation unless the person would like to continue.
Reflection questions:
What thoughts stop you from saying something simple?
What do you assume will happen if you do?
What would it look like to expect nothing in return?
Once you get more comfortable starting small interactions, the next step is learning how to stay in them a little longer.
Level 2: Being curious and asking questions
This is one way for my anxious overthinkers to start building connections with others. Have at least one open-ended question you’d be genuinely interested in asking someone new in your back pocket. Use the question during your daily interactions.
Exercise: Choose one question from this list of open-ended questions and ask the person.
Example question:“What’s one thing that made you laugh today?”
Reflection questions:
Do you focus more on how you’re being perceived or on learning about the other person?
What does genuine curiosity feel like in your body vs. anxiety?
What kind of questions feel natural to you (not forced)?
As you practice being more present and curious, you might start to notice when a connection feels worth continuing.
Level 3: Wanting to continue the connection
Okay, this is exciting. You and the person that you’re talking to seem to have a lot in common. This step can feel especially vulnerable if you’ve been hurt before or are trying not to fall back into old relationship patterns. If that resonates, you might find it helpful to read more about how these patterns show up after a breakup and how therapy can support you in changing them.
Remember, we are spreading kindness, curiosity, and respect for their boundaries (including our own!) when meeting new people.
Exercise: Practice taking the next step to continuing the conversation outside of this one interaction. If the person says no, that’s okay! We tried and can move on.
Example script:“Hey, I really enjoyed our conversation. Would you want to meet up again on [time and date] to do [low-key type of activity that doesn’t need to be expensive]?”
If they say no: “Okay, no problem. Hope you have a great day.”
Additional tip: if you’re sensitive to rejection from others, practice with someone you trust (i.e., family member, friend, co-worker, therapist, etc.) If you’re looking for a therapist, click the link below for a free 15-minute Zoom consultation! I’d love to support you!
Reflection questions:
What makes it hard to take the next step?
Do you wait for the other person to lead? Why?
What would it look like to tolerate uncertainty instead of avoiding it?
And just as important as continuing a connection is knowing when something isn’t the right fit for you.
Level 4: Leaving/Saying “not interested” politely
No one wants to be that person. You don’t want to be rude or mean, but you’re not feeling a connection with the person you’re talking to - and that’s okay.
Again, remember that you are practicing being kind, curious, and respectful to others and yourself.
Exercise: Practice how to get out of a conversation with someone you aren’t feeling a connection with.
Example script: “Thanks for the chat! I’m not interested. I wish you all the best!”
Reflection questions:
What are you afraid will happen if you’re direct?
Where did you learn that saying no is “mean”?
How can you be kind and honest at the same time?
All of this takes time, and it’s okay if it feels unfamiliar at first.
You might still have some questions as you think about dating again. Here are a few that often come up:
Frequently Asked Questions About Dating Anxiety and Self-Sabotage
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Dating anxiety is a type of social anxiety that involves fear, worry, or overthinking when meeting or connecting with new people, especially potential romantic partners.
It often shows up as second-guessing yourself, worrying about how you’re perceived, or feeling pressure to say or do the “right” thing. -
Self-sabotage anxiety in dating occurs when fear or insecurity leads you to act in ways that disrupt or avoid connection.
This can look like pulling away when things feel good, overanalyzing interactions, or assuming a relationship won’t work before it has time to develop. -
You may be ready to date again when you feel open to making a connection with someone new, even if some anxiety is still present.
Signs you may be ready include:You can reflect on your past relationships without feeling overwhelmed
You’re willing to take small, intentional steps forward
You feel curious about making connections with others rather than focusing on the pressure to get it right
If you’re noticing patterns of anxiety or self-sabotage in dating, it might not just be about dating—it could be part of a larger relationship pattern. You can start by reading more about this here. As an anxiety therapist in Chicago, IL, I support individuals who want to feel more grounded, confident, and intentional in how they show up in relationships.
Final thoughts
Dating again isn’t about getting it perfect. It takes patience and practice. Experiment with taking yourself out of your comfort zone. Talk to your local barista or one person a day you meet in your daily life.
The more practice you get, the more comfortable you’ll feel when you do meet someone you might have once believed is “out of your league”. You’ll have built enough confidence to know that, whether they decide to stay or leave, you will not fall apart.
Keep this blog in your back pocket as a refresher, and feel free to share it with someone who might find it helpful.
You don’t have to figure this out alone.
Dating can feel overwhelming,
especially when anxiety or self-sabotage shows up.
If you’re noticing anxiety or self-sabotage in your dating life, you don’t have to navigate it on your own.
A space to ask questions, get a feel for the process, and see if it’s a good fit.
No pressure—just a conversation.
Further reading
