Dating Smart.

I don’t think that anyone would argue that a healthy relationship trumps being alone. However, being alone trumps being in a bad relationship.

Some people are quick to throw in the towel, thinking it’s better “out there,” others hang on way too long. Spoiler alert: people don’t change. A CEO said to me once, “My wife and I spent the first 5 years trying to change the other, and the next 5 years learning to accept each other.”

Today’s post is are some thoughts to consider if you’re dating or considering dipping your toe in the dating pool.

Self-Compassion and Non-Attachment

Before you seek love, give love—to yourself. Self-compassion means accepting your imperfections and celebrating your growth.

Non-attachment doesn’t mean not caring; it’s about releasing the need for outcomes.  For example, enjoy the process of getting to know someone. Even if they seem super cute and nice, remind yourself, “I don’t know one dang thing about him.” His ex could be buried in a field in Wisconsin. He could owe four years of back taxes. He could have a gambling addiction. You just don’t know.

Stay curious about the process rather than hyper-focused on whether a person is “the one.”

Power in Your Femininity

Embrace the strength in your feminine energy. Authenticity, warmth, and confidence draw the right people closer. Your softness doesn’t diminish your power; it enhances it. I 100% recommend the book, Getting to ‘I Do’ by Dr. Patricia Allen. Read it, highlight, make a fake cover for it. Stick by its precepts like it’s your dating bible. Trust me on this one.

Money Matters Some, Wisdom Matters More

A good income is important, but wisdom and emotional intelligence matter more in growing long term wealth and financial stability.

Be clear about your money mindset. Are you a saver, a spender, or somewhere in between? Observing their money habits can be equally revealing. Are they generous, responsible, or avoidant when it comes to finances?

Do they have a good work ethic and enjoy their chosen career path? Are they consistent in their ability to earn? Do they take pride in picking up the check? Are you good at showing appreciation when they do?

If you’re 35 or 45, remember that you’re no longer dating potential. What you see is what you’ll get.

Observe Them, Don’t Tell Them What You Want

Instead of handing someone a blueprint of your ideal relationship, let their actions show you who they are.

For example:

• You want someone who prioritizes family? Observe how they treat theirs.
• You value honesty? See how they handle uncomfortable truths.

People can tell you what you want to hear. It’s what they do that matters.

Todd Bennett, a licensed psychologist, said, “Don’t tell a guy what you want. Observe him for the first two months. What you get in those first two months is the best it will ever be.”

Yikes. Put stock in actions, not words. Words are easy, and cheap.

Play Your Cards Close

Don’t reveal everything right away. Part of building connection is allowing someone to earn deeper layers of your trust. Share at a pace that feels right for you.

And for heaven’s sake, don’t talk about your ex, your divorce, your relationship woes and how every past boyfriend cheated on you. He doesn’t care. If he asks, side step the question and say, “Let’s focus on us, not our pasts,” and save deeper discussions until you’ve had at least 3-5 dates.

Think of this: when you get a new girlfriend, you don’t share your whole life story in one setting. Usually your history is shared here and there over time. You can’t force intimacy by trauma dumping. And talking bad about your ex makes doesn’t make your light shine. Focus on shining, lay down the sack of disappointments and walk toward your future.

Open the sack and root around in it during your therapy sessions. Eventually your ex won’t even be in your vocabulary but it is important to get it resolved with a trusted professional, so it doesn’t unconsciously sabotage your future.

Create Two Lists

1. Things You Like
   Write down what you genuinely enjoy about the person. Is it their sense of humor, their calm demeanor, or how they light up when talking about their passions? This helps you stay grounded in reality rather than getting swept up in excitement.
2. Things That May Become Concerns
   Make a list of things you’re uncertain about or that might be red flags. For example:

• They text less frequently than you’d like—are they genuinely busy or not prioritizing you?
• They talk negatively about an ex—do they have unresolved issues?
  Keep these notes for reflection, but don’t jump to conclusions too soon.

Final Thoughts
Dating smart isn’t about being perfect or having all the answers. It’s about showing up with intention, staying open to learning, and knowing when to stay or walk away. It’s about taking the hits and disappointments in stride, and moving slow enough that you didn’t give too much too soon that now you feel exposed, used or foolish.

Keep your wits about you, He has a lot to prove over a long period of time before he gets a top tier spot in your heart. You love you first.