Dating With Intention: Do’s and Don’ts for Building Healthy Connections

Written By Lochleen MacGregor

Do you ever feel like you keep attracting the same type of person over and over again? Maybe you’ve noticed a pattern of drawing in people who drain your energy, dismiss your needs, or don’t share your values.

If that sounds familiar, you’re not alone. There are many reasons this can happen. Sometimes it comes from old relationship patterns, family dynamics, or unresolved trauma. Other times, it’s simply about not knowing your own values or goals clearly enough to recognize whether someone is truly compatible.

The good news? You can change the pattern. It starts with paying attention to both your own behaviour and the signals others give you in those first few dates.

Here are some helpful Do’s and Don’ts to guide you as you step into new relationships:

Do: Have Fun

Dating isn’t an interview — it’s an opportunity to enjoy someone’s company. If you’re laughing, relaxed, and genuinely enjoying the moment, you’ll get a clearer sense of how you feel about the other person. Fun and ease are foundations of a strong connection.

Do: Be Honest (but Keep It Simple)

Honesty matters, but that doesn’t mean sharing every detail of your past right away. Keep answers short, kind, and to the point. For example:

“I just got out of a long-term relationship that wasn’t a positive fit. I learned a lot about myself during that time.”

This is honest without oversharing, and it keeps the conversation light.

Don’t: Trauma Dump

Sharing vulnerable details too soon can overwhelm a new connection — and worse, it might give the wrong kind of person information they could misuse. Keep it short, respectful, and move on to other topics.

Don’t: List Your “Perfect Partner” Traits

It may feel natural to say what you’re looking for, but giving someone your checklist can backfire. Instead of being authentic, they might mold themselves into what you want (at least temporarily).
A better option is to know your own values and goals, then ask the other person about theirs.

Do: Ask How They Handle Challenges

You can learn a lot about someone by how they deal with difficulties. Do they face things with courage? Do they get curious and reflect? Or do they avoid problems altogether? Avoidance can be a yellow flag in a long-term partner.

Do: Listen to Your Body

Your body often tells you the truth before your mind does. If you feel light, excited, and at ease after a date — that’s a great sign. If you feel tense, uneasy, or drained, pay attention. You don’t need a “logical reason” to step away from someone who makes you feel uncomfortable.

Do: Set Boundaries Early

It’s okay to express what feels respectful and fair to you. For example:

  • “I value equity in relationships, so I’d like to pay for myself tonight.”

  • “My schedule is really full right now. I’ll let you know when I’m free.”

Clear boundaries not only protect your time and energy, they also communicate what you expect from a healthy relationship.

Do: Reflect on Your Own Patterns

Healthy dating starts with self-awareness. If you’re not sure what your values and goals are, or you notice patterns in how you show up in relationships, it’s worth taking time to explore them. After all, how can someone else get to know you if you don’t know yourself?

✨ If any of this resonates with you and you’re not sure where to start, please reach out. We’d love to walk alongside you.

Journal Prompts 📝

  1. What patterns do I notice in the people I’ve dated in the past?

  2. How did I feel in my body after my last date or relationship?

  3. What are three values I hold that I would want a partner to share or respect?

  4. How do I usually set (or avoid setting) boundaries in relationships?

  5. What do I want to feel in a healthy partnership?

Tools & Resources

Lochleen MacGregor
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