Is She With You… or Your Wallet? How Men Over 50 Can Spot the Red Flags
Fellas over 50… if you’re tired of giving and giving without receiving respect or appreciation in return, this one’s for you.
There are women out there who will value you, support you, and meet you halfway, but first, you need to recognize the early signs of someone who may be more interested in what you can provide than who you are.
Hi, I’m Megan Wessels, your wingwoman for singles over 50 who are trying to navigate this modern dating world.
Let’s dive into a few red flags to keep an eye on:
1. She Always Expects You to Come to Her
Women love to be courted, of course. But dating should feel balanced.
If after two dates she’s not offering to come your way or meet in the middle…
👉 Red flag.
Healthy relationships thrive on effort, not entitlement.
2. Her Life Is Chaotic or Disorganized
You’re not looking for someone to rescue.
You’re looking for a companion… someone who brings joy, stability, and peace.
If her life feels like a constant storm…
👉 Red flag.
A partnership should make your life easier, not more stressful.
3. She Suggests High-End Restaurants Right Away
Dating is about connection, not price tags.
You don’t need to impress her with expensive meals.
If she insists on the priciest places…
👉 Red flag.
Choose cozy wine bars, relaxed spots, or anywhere you can actually hear each other and be present.
4. She Wears or Owns Things Other Men Bought Her
In the Throwback Dating community, most women have successful careers, thriving lives, and financial independence.
Their handbags? Self-funded.
Trips to Italy? Self-funded.
If the woman you’re dating is proudly showcasing gifts from other men…
👉 Major red flag.
You’re looking for a partner, not a pattern.
5. She Avoids Talking About the Future
If you want a long-term companion, make sure she’s on the same page.
If she shuts down conversations about where things might be going…
👉 Red flag.
Mature connection requires mature communication.
Here’s the Truth
You deserve a woman who values you, not your wallet.
A woman who lifts you up just as much as you support her.
A woman who wants to take things slowly, hear your stories, build a friendship, and create something meaningful.
Not someone who needs to be rescued… and definitely not someone looking for a financial upgrade.
Trust me, there are so many women like this in the 50+ dating world.
So stop choosing the ones who need you… and start choosing the ones who truly value you.
❤️ 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.
