Are You Trying to Impress, or Assess?
A Better Way for Men Over 50 to Date
If dating has felt frustrating or confusing lately, you’re not alone.
One of the biggest mistakes I see men over 50 make in dating isn’t a lack of effort, it’s a lack of discernment early on. This is especially true for the men I affectionately call the nice guys.
Nice guys are thoughtful. They’re kind. They’re emotionally aware.
But they often make one critical misstep.
They try to impress when they should be assessing.
The Nice Guy Trap
Here’s how it usually plays out:
You meet a woman you’re attracted to.
You like how she looks or how she carries herself.
And without realizing it, you shift into impress mode.
You over-accommodate.
You compliment too much.
You try to be agreeable, easy, and likable.
And then… you get rejected.
And rejection hurts.
The problem isn’t that you’re kind or thoughtful.
The problem is that when you’re focused on impressing, you give away your power, and skip the most important part of early dating.
Early Dating Isn’t About Proving Yourself
Early dating is not about showing someone how great you are.
It’s about discovering whether you’re aligned.
When you stop trying to be chosen and start paying attention, dating becomes clearer, calmer, and far less painful.
Here’s how to shift your approach.
3 Ways For Men Over 50 to Date With More Confidence and Discernment
1. Don’t over-invest too early
Be warm. Be genuine. Be yourself.
But don’t rush to impress someone you don’t really know yet.
Interest should build mutually over time.
2. Focus on connection, not outcome
Instead of wondering, “Does she like me?”
Ask yourself, “How does this interaction feel?”
Be present.
Notice her energy, curiosity, and openness.
You’re not trying to win her over… you’re learning who she is.
3. Assess alignment through conversation
Good dating conversations have balance.
There’s sharing and listening on both sides.
This isn’t an interview… it’s awareness.
Pay attention to cues:
How does she talk about her life?
Does she seem open and positive?
Do your values and lifestyles feel compatible?
The goal is clarity, not performance.
Simple Questions You Can Use To Keep Things Light
You don’t need deep or heavy questions early on. A few easy, natural prompts can tell you a lot:
What are you most enjoying about this chapter of your life?
What made you curious about dating again?
What are some things you like to do for fun?
Do you have any trips planned this year?
(Follow up: Are you more spontaneous or more of a planner?)What are some things you and your kids enjoy doing together?
Ask what feels natural for you, and listen for alignment.
The Shift That Changes Everything
Your dating life improves dramatically when you stop trying to be chosen…
and start choosing well.
Dating doesn’t require perfection.
It requires presence, self-respect, and discernment.
You’ve got this.
❤️ Megan
Megan Wessels
I’m a Wing Woman for single guys over 50 who are trying to navigate this modern dating world. Through my company Throwback Dating I create fun opportunities for singles over 45 to connect organically. No more games, no more dating pressure.
