Are You Ready To Propose?

Ready to propose

We’ve been dating awhile now, so I guess it’s time.
She told me if I didn’t propose, she’s going to break up.
Even though I have doubts, she meets everything on my list.
All my friends are engaged, so it’s time to take the plunge.
I’m getting older and people think it’s weird I’m not married yet.

“Putting a ring on it” might be the biggest decision you will ever make. Popping the question should be free from worries, expectations, handouts, or feeling sorry for her. Entitlement shouldn’t co-exist with engagement.

How long should you wait until you propose? For everyone it’s different. It took years until I was ready.


Are you ready to propose? You are ready to ask her to marry you when you are confident you want to spend the rest of your life with her as she is right now, good and bad.

Need some more things to consider? Here are 9 ways to know you are ready:

1. You’ve found the FOMO cure

I remember it all too well. I was almost engaged to this girl. But when it came down to it, I wanted to hang out with my buddies more than her. On top of that, she couldn’t stand my friends. Either way, no FOMO (Fear of Missing Out) should exist when you’re on a date with her. Nowhere or no group should come before your desire of her.

She’s the apple of your eye, not a dust fleck in it.

If you don’t enjoy every moment with her now, what makes you think you will enjoy the rest of your life with her?

2. You have respect for her family 

Should you ask her father for her hand in marriage? Though some exceptions might be on the table, and traditions are going away, having her family blessing is a matter of respect. Even if relations are strained, family is constant, so don’t alienate yourself by not discussing marriage beforehand with her parents. You’re still marrying into a family regardless if she’s on great speaking terms with them.

3. You know that you know that you know that you know…

It’s healthy to question, to be concerned, and to be nervous. Overall, though, you should be confident in the relationship. Something inside give you a resounding YES vs. “I don’t want to do this, but I guess I should.”

4. Your life is in order

You don’t have to be incredibly wealthy, but you should be in a spot where you can provide for yourself and possibly her. Unless you’ve discussed it and you’re both comfortable living a simple lifestyle, financial disaster is one of the biggest causes of divorce. No ideal time exists, but discuss your finances beforehand. No one wants to be surprised with a huge load of debt on both sides of the equation.

5. You’re ready to be a committed man

You’re tired of the club scene, you’ve reached personal goals, and your mindset is on marriage life, not single life. If you’re not there yet, there is no judgment. Every guy has a need to reach his accomplishments and goals. He has to prove himself as a man first. Some guys need to live life before he’s ready, and it’s ok.

6. You’ve found a cheerleader

I luckily found a wife who is aligned to my goals and we are accomplishing greater things together than I would’ve ever accomplished on my own. That being said, your goals don’t have to be aligned. One of you does have to be supportive of the other, though. You want a life partner. If you want to be a missionary, and she wants to be a Real Housewife of Beverly Hills, then, “Houston, we have a problem.”

7. You’re ready to let go of your ego

If you’re bull-headed, highly opinionated, unyielding, and quit when things get tough or don’t go your way, your design might not be fit for marriage quite yet. Consult a personality engineer first. A redesign may be in order. However, if you’ve mastered the art of compromise, become a good listener, and you’re in it for the long haul, then you’re on the right path for marriage.

8. You’ve given up the false belief that a wife will solve your problems

I have a buddy who tells me he wishes he had a wife because then he wouldn’t be tempted to sleep around. But, a wife is not going to solve your life-long issues. A wife is not going to cure your addictions. A wife isn’t going to complete you and make you whole. A wife isn’t your golf caddy. Pick your own balls up.

9. She’s going to say, “yes”

Maybe you’ve discussed what kind of ring she wants (don’t buy her a sapphire if she wants a diamond). Maybe she’s dropped hints (a little too much and you don’t have anxiety attacks). Maybe her friends are peppering you with questions about when you’re going to drop on one knee. These are all great signs she’s going to say “yes.”

Another option to consider might be pre-engagement counseling. Just make sure you find a good and reputable counselor. I say this because I went through a bad experience years ago. Despite the fact I was in a train wreck relationship, the counselor thought we were “good to go.” However, one of my good buddies just finished seven months of pre-engagement counseling, and really feels confident in his decision now.

No matter what anyone recommends, it has to vibe right in your soul. It should only serve as confirmation to what you already know.

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37 Responses to Are You Ready To Propose?

  1. Eric August 6, 2014 at 1:20 am #

    What a line at the end of number 8!


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