Make a strategic plan for dating with intention

Dating without a strategy is like road-tripping with no map you might end up somewhere interesting, but it probably won’t be where you actually wanted to go. If you know me outside of my coaching work, you might know that I’ve also done a lot of strategic planning with nonprofits, businesses, leadership teams - you name it.

➡️ You can apply the same strategic approach to your dating life… and see big results.

If you’re tired of:

  • “Seeing where it goes” with the wrong guys

  • Getting stuck in situationships that never evolve

  • Feeling like dating apps are a full-time job with no ROI…

…then it’s time to shift into strategy mode.

Here’s my 4-Step Strategic Dating Plan:

It’s simple. It’s powerful. And it will help you stop dating by accident and start dating with intention.

Step 1: Get Clear on Your Vision

Don’t just say you want “a good guy” or “a partner.” That’s vague. That’s like saying your goal is “to get a job.”

What does your ideal life and relationship actually look like?

  • What do your days feel like?

  • How do you handle conflict together?

  • Are you surrounded by friends, kids, pets?

  • Do you want adventure or quiet stability?

Be specific.

🚫 “Wants kids” isn’t a vision.
✅ ”Open to having 4+ kids, a loud house, and hosting big Thanksgiving dinners. Wants to be an involved parent, not just a co-pilot.” is.

Let your mind wander. Be creative. Stand in the future and look around… What do you see? What do you feel? How does your partner treat you? How do you interact with your families? Neighbors? Travel? Etc. What is your life like?

Step 2: Identify What’s Blocking You

You can’t fix what you won’t face.

Think about what’s actually making it hard to move toward that vision. These can be practical or emotional:

  • “I hate dating apps.”

  • “I live in a small town.”

  • “I just moved back in with my parents.”

  • “I feel discouraged.”

  • “I don’t trust myself to choose the right person.”

Tip: Avoid vague scarcity blocks that include the idea of ‘lack’ such as “there aren’t any good men” or “I don’t have enough time.” It’s hard to fix something that doesn’t exist. Define your blocks as something you can actually identify such as “I don’t know where to find the good men” or “I already have a busy schedule”

Step 3: Choose Actions That Move You Toward Your Vision

🪄 Here’s where the magic happens.

Once you’ve identified the blocks, brainstorm at least 10 things you could do to work around the blocks and move you closer to your vision. Push yourself to come up with 10 ways to move toward your vision. Yes, 10. Even the messy, stretchy ones. Be creative. Think outside of the box.

  • Hate apps? 💡You could look for in-person events or speed dating.

  • Live in a small town? 💡You could look for virtual dating mixers or events in nearby cities.

  • Feeling shy? 💡You could join a women’s group to meet new people and ask some of them to introduce you to people they trust.

  • Not meeting aligned people? 💡You could rework your dating profile to reflect your actual values and vision and be more clear on who you are an what you’re looking for.

You don’t have to do them all. But brainstorming will help you see you have options even if they are outside of your comfort zone. Especially if they are.

Step 4: Commit to a 90-Day Implementation Experiment

Now comes the important part: actually doing the thing.

Once you’ve got your list, it’s time to stop dabbling and start testing.

Pick one, two, or three actions from your list that feel promising (even if they stretch you a little). Then commit to those approaches for the next 90 days.

  • That might mean showing up to one in-person event each week.

  • Or asking a few friends to set you up with people who might be a good connection.

  • Or spending 30 minutes every Sunday writing thoughtful messages on a dating app.

  • Or putting yourself out there on social media to let people know what you’re looking for.

Give yourself time to implement and observe.

Go all in on reaching your vision.

See what happens.

Take notes.

Notice how you felt and what you might want to expand on and try again.

See where you can refine your approach.

Keep your vision in focus, and don’t get distracted by relationships that aren’t aligned with it. If something feels off, ask yourself, “Is this moving me closer to reaching my vision?” If not, you know that person is not someone you want to move forward with.

👉 This is your experiment. You are the strategist. Let your data (not your doubts) guide the next move.

Want help creating your personal Strategic Dating Plan?

You don’t need more dating hacks. You need a plan that reflects who you are and what you want without apology or explanation.

📅 Book a free call with me and we’ll talk about how you can claim your vision and create a path to reach it.

You deserve more than guesswork. Let’s make your dating plan today!

 You've got this. 💕

Paige Dempsey

I am a feminist life and relationship coach for women.

https://www.paigedempseycoaching.com
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