Should You Marry Her? Ask These Questions First

There are a lot of questions before “Will you marry me?” And most of them, you need to be asking to YOURSELF.

James Michael Sama
14 min readNov 3, 2023


You’re going to make an infinite amount of important decisions in your life, but as far as the most important go, proposing to a woman is at the top of the list. Top 5 definitely. Maybe the top 3. Maybe even…the most important.

Virtually every other area of your life is going to be affected by this decision. Not just whether or not you get married, but who you choose to marry.

This woman is going to be your teammate in life. Your support system. Your cheerleader. Your confidant. Your forever-date. Your parenting partner (maybe). Your travel partner.

She’s going to be the person who stays by your side for the rest of your life, while you stay by hers.

That, to me at least, is the essence of marriage. It’s not a trial run. It’s not something to be taken lightly. You don’t just “give it a shot.”

The decision to propose, to quite literally propose that you and this one person spend the rest of your lives together is one that a man must be one thousand percent certain about before he gets down on one knee.

You can go to everyone you respect in your life for advice, feedback, and insight — but the only person who really knows what’s best for you is you.

The following questions, among many others, are just the starting point for conversations that I have with private clients (both men and women) to help make sure they’re choosing the right partner.

Ask yourself these 12 questions before you swipe your card for that diamond ring:

1: “Am I really, truly, genuinely READY for this?”

That’s right, the first question here isn’t even about the woman you’re (possibly) marrying!

It’s about you, because she could be the best, kindest, most genuine, most selfless, loving, caring, and dedicated woman on the planet, but if you, my friend — are not fully ready to make a lifelong commitment to her, then there is always going to be something lingering in the back of your mind…



James Michael Sama

I help you evolve into the ultimate version of yourself. Life & Executive Coach. Multi #1 writer. Trusted by: CNN, CNBC, NY Post, CBS, more. Say hi! @JamesMSama