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 this blog will be your guide. 

If you’re experiencing dating anxiety or noticing patterns of self-sabotage anxiety, you’re not alone. As an anxiety therapist in Chicago, IL, I often work with clients who feel stuck between wanting connection and fearing rejection. These small, intentional steps are designed to help you move through anxiety without letting it control your actions.

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?

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 (add link to 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)?

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. 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?

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?
  

Final thoughts

When it comes to dating, 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 if you need a refresher, and feel free to share it with someone who might find it helpful.

If you’re noticing patterns of self-sabotage anxiety in your dating life—especially after a breakup or divorce—you don’t have to navigate this on your own. 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.

If you’re curious about working together, you can schedule a free 15-minute Zoom consultation below. It’s a space to ask questions, get a feel for the process, and see if it feels like a good fit.

This can be a new way of showing up in relationships.

Not by forcing confidence—but by learning how to stay with yourself when anxiety shows up.

Feeling stuck in dating patterns that don’t feel good?

If you’re noticing dating anxiety or patterns of self-sabotage anxiety, you don’t have to figure this out on your own. Therapy can be a space to slow things down, understand what’s coming up for you, and practice showing up differently in your relationships.

As an anxiety therapist in Chicago, IL, I work with individuals who want to feel more grounded, confident, and intentional in dating and relationships.

Curious if this could be helpful for you?

Schedule a free 15-minute Zoom consultation to ask questions, get a feel for the process, and see if we’d be a good fit.

No pressure—just a chance to explore what support could look like for you.