He needs to ask his adult children before proposal!

It’s two months since the OP went on holiday and she never let us know if he did propose so there’s really no point in continuing to give advice.

It can be a serious issue involving second relationships including mine.

OH is a widower with 3 daughters, a large extended family, and considerable property, within a few weeks of us dating he made it clear that marriage was not an option. Everyone knows what the relationship is and have accepted me without reservation, not as his wife’s replacement but as dads companion. With no worries about me stealing their inheritance.

The main attraction is that I am valued as a partner and we have many joint interests and similar values. Every relationship different and in many cases it is the woman who has the wealth, whatever it is make sure you are getting a good deal out of living together.

Disregard above it’s been so long I forgot I responded.

In the event I were likely to remarry in the future, my choice would be for my 'intended' to quietly make one of my children aware he was going to propose. I see nothing strange in it.

You have the property which you want to protect for your grown children. Your partner has debts and no property to speak of by the sounds of it. He is going to basically ask his daughters opinion of you uniting in marriage. Have you asked your GC their opinion of marriage to your partner just curious.
I would have had my will sorted out and personally I would leave the marriage idea for now. I would see how your relationship progresses as there appears to be trust issues which would make me wary.

I assumed the same as Yoga:
I would not have taken that to him going to ask permission but rather to let his daughter know in person, particularly if her mother is deceased.
I thought that he was just trying to keep the daughter in the loop.