Worksheet: Dating Securely

This worksheet is designed to support you in dating with a secure mindset. Secure dating means showing up authentically, respecting your needs and boundaries, and allowing trust and intimacy to develop gradually. Use these prompts to prepare for dates, stay grounded during them, and reflect afterward. Just a reminder, rejection is redirection and not a reflection of your worth. Some people just aren't a good fit.

1. Preparing with a Secure Mindset

Ask yourself before dating:

✔ What values do I want to guide me in dating (e.g., honesty, curiosity, respect)?

✔ What are my non-negotiables (behaviours I will not compromise on)?

✔ What are my personal boundaries around time, communication, and intimacy?

✔ What qualities do I bring into relationships that I am proud of?

✔ How will I remind myself that rejection is not a reflection of my worth? How will I be there for myself when I am rejected?

2. Secure Behaviours During Dating

Secure behaviours to practice on dates:

✔ Share honestly about yourself without oversharing too quickly.

✔ Allow connection to grow gradually rather than rushing emotional or physical intimacy.

✔ Stay curious about the other person instead of trying to prove your worth (focus on whether you like their qualities or not instead of trying to be chosen).

✔ Notice red flags without minimizing or excusing them.

✔ Express your needs clearly and calmly (e.g., “I’d like to take things at a steady pace”).

✔ Take breaks if you feel anxious or shut down, instead of forcing yourself to keep going.

✔ Balance independence with connection—check in with yourself as much as with the other person.

3. Secure Communication Practice

Try using these secure communication sentence starters:

• "I feel ___ when ___. What I need is ___."

• "I want to get to know you at a pace that feels comfortable for me."

• "I value honesty, so I’d like to share ___."

• "I enjoy ___. Would you like to do this together sometime?"

4. Reflection After Dates

Use these prompts after a date to reflect and stay aligned with secure patterns:

• Did I feel safe and respected during the date?

• Did I stay connected to my values and boundaries?

• Did I notice any "red or yellow" flags? If so, how did I respond?

• Did I share honestly without abandoning myself?

• How did my body feel during the date (calm, tense, excited, uneasy)?

• Do I feel curious to see this person again, or do I feel pressured or drained?

• Did I practice secure behaviours such as pacing, self-regulation, or expressing needs?

• What am I proud of in how I showed up?

5. Building Secure Capacity Over Time

✔ Practice grounding or self-regulation before and after dates (breathing, journaling, movement).

✔ Notice if old patterns of pursuing, avoiding, or people-pleasing show up, and gently redirect to secure behaviours.

✔ Share your dating reflections with a trusted friend, therapist, or journal to stay accountable.

✔ Celebrate small steps—secure dating is built through consistency, not perfection.

✔ Remind yourself: it is safe to take your time, trust your needs, and allow genuine connection to grow.

Dating securely is about balance: staying true to yourself while being open to another. By preparing intentionally, practicing secure behaviours, and reflecting after each date, you strengthen your capacity for healthy, fulfilling relationships.