Should You Stay or Walk Away? The Brutal Truth About Dating Someone While You’re Both Separating
Gender
Male
Age
39 years old
Race
Hispanic
Question:
Hi, I met Lindsay in college. We are both non-traditional students and we’re both married. Both of us have separated from our spouses and we’re going through trials and tough times in both our previous and current situations.
I’m seeing a lot of red flags in her, and she says she sees some in me too. When she starts feeling this way, she shuts down and doesn’t communicate with me for days. She doesn’t ghost me or block me — she just stops responding.
I feel really, really good when things are going well between us, but really bad when they’re not. I want to know: is it better to cut my losses and walk away, or should I hold out for the good times that feel like they’re in the making?
There’s much more to the back story — her husband finding out, my wife, the trips, the kids, everything.
Answer:
All right, man. Let’s cut the sugarcoating because you don’t need comfort — you need clarity.
You messed up.
Big time.
You’re 39 years old, married, with kids, and you decided to jump into something with another married woman who’s also falling apart emotionally. You thought the grass was greener, and now you’re sitting in a mess that’s burning from both ends.
And here’s the part you need to hear clearly:
This woman is not your solution — she’s another problem.
You said it yourself: she shuts down for days, doesn’t communicate, plays emotional hide-and-seek, throws out red flags like confetti — and then calls you out for having some too. This isn’t chemistry. This isn’t destiny. This is two broken people trying to use each other as a bandage.
And brother, bandage relationships never work.
They just prolong the wound.
Let’s talk reality for a second.
When you’re 19 or 21 in college?
People are still figuring themselves out. They’re growing, evolving, shaping who they’re going to be.
But at 39?
People are who they are.
Her issues? They’re not temporary.
Her shutdowns? Not a phase.
Her emotional inconsistency? That’s her personality.
Same goes for you — the parts of you she calls “red flags”?
She’s not wrong.
You’re in a chaotic chapter of your life. You made decisions driven by emotion, escape, and timing. But that’s not love — that’s crisis bonding.
Now let’s talk consequences.
You already blew up the trust in your marriage. That’s hard enough to fix. When kids are in the picture, it becomes 10x harder. It takes years — and even then, the relationship never looks the same again. That’s the price you pay for taking the shortcut instead of leaving the right way.
And if you think this new woman is going to give you peace?
No chance.
She’s got her own demons, her own chaos, her own unresolved marriage, her own emotional instability. She can barely communicate during a tough moment — and you think she’s capable of building something stable with you?
Absolutely not.
Here’s the truth you’re avoiding:
You two are not in love.
You’re trauma bonding.
You’re both hurting, lost, confused, lonely, and using each other to escape your real problems.
And guess what?
That type of bond falls apart the second the chaos calms down.
Your future — your real future — depends on what you do next. And you don’t have the luxury of wasting time. You’re pushing 40. Every year from here on out matters, because dating in your 40s isn’t a playground. Most single people in that age range aren’t exactly walking around without baggage. You’re in a tougher market now.
So here’s the bottom line:
Take the L.
Walk away.
Use this as a wake-up call, not a new relationship.
Fix yourself first.
Handle your separation properly.
Heal.
Get stable.
Clean up your situation before you bring someone new into your life.
And when you start dating again?
Move smarter.
Move slower.
Identify red flags early.
Cut things off sooner.
Stop getting emotionally tangled with the first person who gives you attention while you’re vulnerable.
You already lost once.
Don’t lose years of your life repeating the same pattern.
Good luck — you’re gonna need clarity and discipline more than romance right now.
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