I was involved with someone for five years (in my early to mid-40's). There were many break-ups, multiple counselling sessions, many issues, blending families, personality conflict, parenting differences, household issues, income level disparities, etc.

The final breakup left me broken emotionally; I’ve finally emerged sane and stable.

But four years later, I’ve been unable to move forward with anyone else.

He was the love of my life despite it all. I’ve learned that he met someone else within five months and married her last year.

I’ve since heard that the marriage ended two and a half  months later, and that he recently broke up with another women after only six weeks.
Whenever he has problems, he reaches out to me wanting some insight and perspective on things we experienced together which relate to his current issues. Very cautiously, I’ve provided some feedback.
Recently, the communication’s intensified. He expresses interest that he wants to be friends as he recognizes that I was a kind and caring person and he needs to rebuild his life in order to surround himself with people who were kind and caring to him.

I’m trying to understand why he continues to reach out to me and wants to be friends now, with a lot of loving words exchanged, lots of bantering and flirting.

It gives me one impression but he insists that he wants to remain friends.
I realize that our past intense relationship was very frustrating to both of us. He now wants to travel the world and would like to share that with someone.

I’ve built a home and great career here, and have family and friends. I’m confused with his mixed messaging.
I’m trying to keep things in the friends’ zone. Please share your insights on this.
Troubled and confused.

This man is a carrier of “trouble” and “confusion.” His outreach to you seems entirely selfish, not a gesture of real and lasting friendship, nor a relationship.

He wants two things: Assurance that he’s not such a bad guy even though he can’t sustain a romantic relationship. And he wants some companionship in his terms only, i.e. for travel since this is what he wants to do now.

There’s no consideration for how he affected your life in the past, or how he’d disrupt it if you joined him now.

The longer you dwell on the past relationship, the longer it’ll take you to move on. And joining forces with him now, even as friends, could be disastrous for you, emotionally.

He’s a taker, not a giver. Wish him Bon Voyage.

When is an ultimatum appropriate in a relationship?

Wondering About Timing

Once you start wondering, an “ultimatum” has to be directed to yourself.

You’re the one who’s accepted something that’s been bothering you for some time. You’re the one who thinks the current situation  isn’t right, that it’s causing you unhappiness, and  preventing you from moving forward with what you really want.

It doesn’t matter if it’s been six months, one year, or five. You need to clarify your own needs and wants in the moment.

   Once you face yourself honestly, there’s no need for an attack approach, anger, or accusations. Just state what you feel, and what you’ve now recognized is how you want and need to feel.

That open, straightforward revelation gives the other person the opportunity to respond.

If you’re ready for that confrontation within yourself,  you must also be prepared for the other person to feel differently.

My son’s been in a nine-year relationship, on and off. His partner’s always been controlling, demanding, spoilt, disrespectful, and outright rude to me, my daughters, and other family members.
He announced his engagement several week ago. I told him it was a mistake.
He’s now angry with me.
I don’t understand how he allows her behaviour and the way she treats everyone. He’s pulled away from me the last few years because of her demands.

I believe he’s blinded by her. I’m also concerned that she smokes weed.

Mom Needs Advice

Face reality: He’s chosen to be with her. After nine years, he’s accepted whatever she does that you don’t like, and your opinions are driving him away.

I’m sure that in your heart you want to have an ongoing relationship with your son. It can’t happen unless you stop your criticism. That’s the only way you can give him support, if he ever needs it.