Dating Over 50: Are Your Girlfriends Helping or Hurting?
(A version of this article previously appeared on Sixty & Me.)
Dating over 50 is brave.
Tender.
Hopeful.
And yet—sometimes the hardest part isn’t the men.
It’s the people sitting across from you at lunch, clutching their wine glasses, nodding sympathetically while inadvertently dragging your love life into the gutter.
One of the biggest influences on your success in the dating world isn’t your dating profile, the dating apps, or even the size of the dating pool.
It’s your girlfriends.
If you’re dating over 50, or even considering it, your friends—and your kids—are absolutely influencing how you feel, how you choose, and how long you stay stuck.
When Women Undermine Other Women (Without Meaning To)
I call it misery poker.
You know the game.
You share something hopeful:
“He seems kind, consistent, like a good guy.”
Another raises the ante:
“Well, my last bad relationship started that way.”
“Men our age don’t really want commitment.”
“Be careful, especially with older partners, they don't learn new tricks.”
Soon, the table is full of warnings, projections, and recycled disappointment from previous marriages and old heartbreaks.
No one is being malicious. But a consistent pattern emerges: Optimism gets punished.
This is how women unintentionally teach each other that wanting true love after a long time alone is naïve, or worse, unsafe.
And it’s devastating.
Because the most important thing in dating over 50 is your attitude, and it needs to be hopeful!
They’re not trying to sabotage you. They’re just letting off their own steam, trying to process their own pain, and recruiting you into emotional solidarity.
If you succeed, what does it say about them? Misery loves company is a cliche for a reason.
But when women repeatedly undermine other women’s hope, it creates a quiet agreement:
“Let’s not want too much.”
And that agreement will cost you at just the time of life that ALL your focus should be on what YOU want (finally.)
The Danger of Outsourcing Your Dating Intuition
Many older women tell me, “I just want a second opinion.”
When you’re dating over 50, it can feel comforting to run everything by your girlfriends. It’s even fun to send pics of a text thread and go through the play-by-play with your nearest and dearest in an attempt to understand what your potential suitors might be thinking. Every fledgling relationship becomes a group project.
But here’s the coaching truth:
Your friends can’t (and shouldn’t) make YOUR decisions. Your friends are not in your body.
They don’t feel your nervous system. They don’t experience your emotional needs. They don’t know which compromises feel workable to you.
They’re responding from their past experiences, not your present reality.
This is the time in your life when you should be honing your intuition about your 3H needs, rather than outsourcing it to anyone who might be more comfortable if you stay single.
Take a moment to consider where your friends might be coming from when they fill your head with horror stories, warnings and general negativity about men or dating and then decide if you want to “go down” with them.
If you decide to stay on “Team Hope,” you have two choices: get your friends on board with a clear request or hang out with different people. (This is why I have group coaching with Master the Art of Love.)
In group coaching, women learn how to:
Support each other without projecting
Speak honestly without undermining hope
Normalize fears without amplifying them
Celebrate wins without jealousy
Call each other forward—to honor our ideals
And Then There Are Your Kids…
Ah yes. The adult children. Hopefully, yours are loving and well-meaning, but it doesn’t make things less complex when new love comes on the scene.
When you start dating as an older woman, your kids may react in surprising ways, especially if it's been a long time.
Some feel competitive:
“I’ve been your main emotional support. Where do I fit now?”
Some feel possessive:
“I don’t want to share you.”
Some feel wary about your mental health:
“I don’t want you hurt again.”
Some are worried about their own life:
“What if HE spends my inheritance?”
And some feel uncomfortable with the idea that you’re still a sexual, desiring woman.
(That one doesn’t get said out loud, but it’s there.)
So they ask pointed questions. They raise eyebrows. They offer “concern.” And suddenly, you’re managing their feelings instead of honoring your own.
I think the thing children need most, even adult children, is to see you happy. Subconsciously, it teaches them that happiness, into old age, is possible for them too. So they may try to convince you (and themselves) they’d be happier for you to avoid risk, the truth is, everyone would be happier if you found the right person to share love with for the rest of your life.
Your kids don’t need to approve of your dating experience, but it sure would be nice to have their support. And since you can’t choose new kids, this challenge requires a frank conversation about your vision for your future and how love and your relationship with them fit into it.
Modeling self-determination and joy as you age is not selfish; it’s probably the greatest gift you can give them.
The Good News: Women Can Be Powerful Allies in Love
Here’s the good news: women can also be extraordinary allies in dating.
Good girlfriends:
Celebrate your courage
Ask thoughtful questions instead of planting doubt
Help you slow down so you can assess your 3H criteria soberly.
Care about your safety and your happiness
They ask:
"How do you feel with him?”
“Does this relationship support your emotional stability?”
“Is there mutual respect and real emotional intimacy?”
They don’t dismiss red flags, but they also don’t panic over the little things.
They understand that dating over 50 isn’t about perfection. It’s about lifestyle compatibility, emotional maturity, and shared values.
This is the difference between women who keep each other stuck—and women who help each other grow.
The difference may seem subtle, but it’s profound.
Dating over 50 already can feel a bit lonely as you search for the right places to find eligible people with your interests, or dare to go into the unchartered territory of online dating.
So if you want to feel less alone and more grounded and have more fun, you will pay attention to surrounding yourself with hopeful, positive voices. Veer towards those who make you feel more excited to date and away from those who build your fears. It’s simple to figure out…
Questions to Ask Yourself
Before you share your dating life, ask yourself:
“Is this person invested in my growth or in keeping me company in disappointment?”
And before you take advice, ask:
“Does this expand me or shrink me?” Do you admire how this person approaches love and/or dating?
You can control what you share with whom and who you let whisper in your ear.
Here’s me whispering: love has no expiration date. Now is the best possible time for you to muster up all your courage and hope and go for it.
Why Group Coaching Changes Everything
I include group coaching inside Master the Art of Love because there’s a massive difference between:
Unfiltered opinions
And guided reflection led by a dating coach
In group coaching, women learn how to:
Support without projecting
Share wisdom without undermining hope
Normalize fear without amplifying it
Spot unhealthy dynamics without becoming cynical
It becomes a safe space—not to complain about men—but to build emotional skill.
Ready for a Different Kind of Support?
If you’re dating over 50 and want:
Confidence instead of confusion
Discernment instead of fear
Real tools for building emotional intimacy
Then you don’t need louder opinions.
You need better guidance.
Check out my free webinar 3 Secrets to Finding and Maintaining Healthy Love:
Love,
