Dating Dos and Don’ts: What to Do When You’re Ready for a Lasting Relationship

Over the years, I’ve had the honor of counseling individuals and couples through every stage of a relationship. From dating and deepening connection, to marriage, partnership, and building a family.

And one thing I see again and again when people are ready for “the one?”

They start asking bigger questions:

• What are my non-negotiables in a partner

• What are my deal breakers?

• What patterns do I need to change?

  
  

This guide is a set of practical reflection questions and a list of Dating Dos and Don’ts that have helped my clients navigate dating with more intention, self-awareness, empowerment, and clarity.

Know Thyself

Self-understanding creates natural standards. You don’t have to force them; they rise up from within you. And that kind of clarity? It helps you sort the false starts from the love that lasts - quickly.

Dating becomes less about impressing someone and more about asking:

Does this connection reflect who I am and align with my relationship goals?

Questions to Deepen Your Self-Knowledge Before Dating

Want to save yourself a lot of time and unnecessary pain? Know what you are actually looking for. Not just tall, dark, and texts back quickly. Think deeper.

What values matter most to you? Kindness? Growth? Emotional availability?

Also ask: How do I want to feel in a relationship?

Cherished. Supported. Energized. Like yourself? 

The questions below are there to help you get your emotional priorities and non-negotiables in order. Keep them handy. Not to be rigid, but to help you stay grounded.

1. What do I value most in relationships, romantic or otherwise?

(Honesty, curiosity, compassion, ambition, loyalty, humor, emotional maturity, dependability, shared purpose, intellectual depth, mutual support, kindness, creativity...)

Think about what makes you feel safe, respected, and alive in close relationships. These are often your core values.

2. What kind of support do I long for in a partner?

(Someone who celebrates my strengths, affirms my identity, listens without judgment, challenges me to grow, supports my goals, respects my space, makes me feel safe and seen...)

You deserve a relationship where your needs don’t feel like burdens.

3. What patterns have shown up in past relationships that I don’t want to repeat?

(Fear of abandonment, people-pleasing, miscommunication, dating without alignment, avoiding hard conversations, staying for potential instead of reality, or choosing what’s familiar instead of what’s healthy...)

This isn’t about shame. It’s about learning. Patterns don’t mean you’re broken. They mean you’re human. And you’re allowed to choose differently.

4. What kind of moments make me feel safe, seen, and cared for?

(A long hug, deep eye contact, words of encouragement, shared laughter, someone remembering the small things, a supportive check-in, sitting in silence without pressure...)

These are clues to your love language, which is helpful information to know when dating. Read more about love languages here.

5. What’s my relationship to boundaries, and how do I want that to grow?

(I avoid conflict to keep the peace… I set boundaries but struggle with follow-through… I’m good at protecting my time, but want to grow in emotional boundaries…)

Boundaries are not walls. They’re invitations to deeper connection with the people who are willing to honor them and support your needs.

6. What Makes You Feel Most Alive?

(Laughing with a close friend, hiking through the woods, hosting a game night, reading for hours, building something with your hands, planning your next trip, or getting lost in a creative project)

Think about when you feel calm, energized, connected, or simply free to be who you are.

These aren’t just hobbies or preferences. They’re windows into how you thrive emotionally, spiritually, and creatively, and should have space in your next relationship. 

These aren’t questions you need to answer all at once. 

If you’re having a tough time with these questions, talk through them with a therapist, trusted friend, or family member. Sometimes the people who know us best can reflect back what we can’t always see clearly.

Getting to know yourself isn’t a prerequisite for dating. It’s part of the process.

But the more rooted you are in who you are, the more clearly you’ll recognize when something, or someone, aligns.

Dealbreakers Matter Too

As important as it is to know what you want, it’s just as important to be clear about what you won’t accept.

Sometimes we meet someone who has so much going for them. They are charming, smart, attractive, fun, but there’s one thing that crosses a line for us.

Maybe they drink heavily, and you’re sober. Maybe they smoke and you don’t want that in your life. Maybe they don’t want kids, and that’s non-negotiable for you. Maybe they’re unemployed and not actively working toward change.

These aren’t just preferences. They’re dealbreakers.

And when we like someone, it’s easy to bend the rules. We tell ourselves we’re being open-minded. We say, “Well, nothing’s perfect.” And while that’s true, compromising on your core needs almost always leads to resentment, confusion, or pain down the line.

So take a moment and ask yourself:

What are my true dealbreakers in a relationship?

These might be about lifestyle, values, long-term goals, or emotional availability.

Write them down. Keep them close. Not to be rigid, but to value the time and energy you are putting into your next relationship.

Top Dating Tips: What to Do When You’re Looking for a Real Relationship

✅ 1. Let Yourself Be Known…Gradually

You’re not interviewing for a job. You don’t have to frontload your whole story on date one. Real intimacy builds in layers.

Reveal yourself slowly. Show up honestly. And notice: Are they curious about who you really are?

“Love is a vessel that contains both security and adventure, and commitment offers one of the great luxuries of life: time.”

— Esther Perel 

✅ 2. Use Communication as a Filter, Not Just a Skill 

The way someone responds to honesty is more important than how charming they are at dinner.

Try this: set a gentle boundary. Speak up about something small that matters to you. Watch what happens.

“These conflicts that we are trying to avoid are really relationship tests. A lot of times we live in fear of the person’s reaction. But sometimes the person’s reaction is the reason why the relationship needs to fundamentally change or end.”

 — Kwame Christian, Esq.

The right people won’t be scared off by your clarity; they’ll be drawn in by it.

✅ 3. Ask Real Questions 

Go beyond small talk. Ask something that invites meaning:

• What’s something you’re looking forward to right now?

• What helps you feel grounded when life gets stressful?

You don’t need a script. Just sincere curiosity.

✅ 4. Lead With Confidence, Not Ego

If you’re reading this right now, chances are you deeply value meaningful connection. That tells me you’re not here to play games, you’re here for something real.

Take a moment to acknowledge what makes you special:

• Are you amazing with people?

• Do you bring warmth and humor into every room?

• Are you thoughtful, resilient, creative, or deeply loyal?

• Can you cook like a pro, craft with care, or light up a conversation?

Know what you bring to the table. That’s not arrogance. That’s clarity.

You don’t have to puff yourself up or pretend to be perfect. You just have to stay rooted in your worth.

Confidence says, “I know who I am, and I’m open to love.” Ego says, “You’re lucky to be here.” Confidence says, “I’m glad we both showed up.” People can feel the difference.

Your confidence creates safety. It helps you show up fully, listen openly, and stay grounded no matter how the date goes.

✅ 5. Reflect After the Date—Not Just About Them, But About You

 Instead of just wondering “Did they like me?” ask:

• Did I like how I felt around them?

• Was I able to be myself?

• Did something feel off, even if I can’t explain it yet?

  
  

Dating is about choosing, not just being chosen.

Common Dating Mistakes That Get in the Way of Real Connection

🚫 1. Don’t Confuse Familiarity with Compatibility

Sometimes what feels like a “spark” is really your nervous system recognizing an old pattern, one that you’re working to outgrow.

Familiar doesn’t always mean healthy.

Notice how your body feels around them. Anxious? Dismissed? Like you’re shrinking? That’s not chemistry. That’s survival mode.

🚫 2. Don’t Abandon Your Standards Just to “See Where It Goes”

Saying yes to everyone just to stay open can lead to emotional burnout.

Curiosity is beautiful. So is discernment.

You’re not being too picky for wanting shared values, emotional maturity, and respect.

You’re not just looking for a date, you’re looking for a partner.

🚫 3. Don’t Ignore the Little Things That Matter to You

If emotional safety is important to you, don’t explain away disrespect.

If you want consistent communication, name it.

If kindness is a non-negotiable, don’t justify cruelty as humor.

You don’t have to downplay your needs to be lovable.

The right person will want your full, unfiltered self: hopes, quirks, and all.

Offer grace, but honor your standards.

“The most successful couples are those who are good friends, who show respect and empathy, and who can repair after conflict.”

— Dr. John Gottman

🚫 4. Don’t Ghost, But Don’t Overexplain Either if it's not the Right Fit

You don’t need a five-paragraph essay to justify your intuition.

A simple, kind message is enough:

“Thanks again for meeting up, I really enjoyed getting to know you a bit. I don’t feel a romantic connection, but I’m wishing you all the best.”

Clarity is kindness. Exit with respect for both people involved.

You Deserve to Feel Chosen and Empowered

Let’s be honest: dating can be disorienting.

It asks you to show up with hope, discernment, patience, and just enough vulnerability to risk being seen.

But here’s the truth:

Dating with self-awareness doesn’t make you harder to love. It makes you clearer.

And clarity? That’s magnetic.

When you know what you value, how you want to feel, and what you’re no longer willing to compromise, you stop wasting time on “interesting characters” for the plot and start holding out for a higher caliber of partnership. And you learn to gently and confidently walk away from anything less.

Want support while navigating love, dating, or relationships?

I’ve been fortunate to help many of my clients find and keep lasting love, and it’s one of the greatest sources of fulfillment in my work. If you’re feeling stuck, overwhelmed, or ready to grow in a new direction, therapy can be a powerful place to start.

If you're ready to take the next step, I’d be honored to support you.

➡️ Schedule a session with me.

With Warmth,

Dr. Kristen Aycock