When To Propose And How To Pop The Question

Men's Dating

3 Signs You’re Ready to Propose (and How to Pop the Question)

Hunt Ethridge

Written by: Hunt Ethridge

Hunt Ethridge

Hunt Ethridge is the co-founder and CMO of the MatchmakingAcademy.com as well as senior advisor and board of directors at other firms.

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Edited by: Jon McCallister

Jon McCallister

Jon came to DatingAdvice in 2016 with more than 15 years of editorial experience behind him. He has experience editing, writing, and designing at numerous publications, including the Gainesville Sun. Jon enjoys researching emerging trends and seeking out the companies, organizations, and individuals making an impact in the modern world of dating. He excels at working closely with writers and editors to improve the quality of online content.

Reviewed by: Amber Brooks

Amber Brooks

Amber Brooks is a dating and relationship expert who has penned over 1,800 lifestyle articles in the last decade, and she still never tires of interviewing dating professionals and featuring actionable advice for singles. She has been quoted by the Washington Times, Cosmopolitan, The New York Post, and AskMen.

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Discuss This! Discuss This!

When I proposed to my wife, she laughed at me. Definitely NOT the reaction I was hoping for!

Once she realized that I was serious and that it wasn’t, in fact, a joke, she accepted and hugged and kissed me. But man, for a few seconds there, every guy’s worst nightmare was happening! I botched the proposal. Well, not botched, but it definitely wasn’t the proposal I had in mind, either.

Proposing is something that we (hopefully) only do once, so we want to make sure it is the right time and that we do it the right way.

But knowing when to propose can be a hard decision for a guy! No hard and fast rules exist, and for everything I cover in this article, you can find an exception. But you need to understand and experience some things before popping the question. We could discuss how you know for hours, but here are a few practical tips to help you start thinking.

1. You’ve Put In the Time

While we have all heard of whirlwind romances and marriages (my parents met and were married within a year!), most experts agree that you should spend a good deal of time together before proposing. The puppy-dog infatuation stage of love can last anywhere from two months to 2 years. After that, the crazy love hormones subside, and we move into a more mature love. 

So, we want to ensure that any lifelong decisions are made in the right frame of mind. Wait until the rose-colored glasses have come off. What started off as a cute quirk can easily move into something that annoys you to no end. You need to see how you deal as a unit.

Hunt advice on when to propose
Don’t propose until you’ve experienced real-world challenges with your partner.

Another thing about time is that you must experience real-life challenges together as a couple. Part of working as a unit is overcoming obstacles. How well a couple navigates challenges can help determine the strength of that relationship. It’s easy to envision marriage and “happily ever after” when things are going well, but what about when they’re not? 

 Also, I think being together for a full calendar year is important because you want to see how you approach all types of weather, holidays, vacations, and other occasions. If one person wants to be outdoors every day all winter, that might not be the other person’s cup of hot chocolate. Figuring out where to spend holidays and when to introduce each other to family is another great microcosm of communication.

2. You Think in Terms of “We” Instead of “Me”

Somewhere along the line, your thinking moves from “She and I” to “Us.”  Three entities exist in a relationship: you, me, and us. All three need nourishment to succeed. When friends ask about future plans, do you automatically consider you and your partner a unit? “Oh, that sounds fun, we’d love to come!” They may not have asked, specifically, for your girlfriend to come, but as a “We,” you just consider yourselves happily joined at the hip.

Hunt quote about nourishing relationships
Before proposing, make sure you see you and your partner as members of the same team.

When you think about future plans yourself, you envision her in them. It can be as small as a weekend plan. When someone asks, “Want to come camping with us?” You may respond: “Ooh, that might be fun, let me check with Bree to see what she thinks.” 

Or it can be something much larger. Maybe you once envisioned yourself in a swanky downtown apartment with a wooden bar. Now, you’re wondering how much land and bedrooms you might want if you get a house in the suburbs.

3. You Have Talked About the Tough Questions

Time is nothing without substance. That’s why you should discuss some tough topics to find out if you’re truly compatible before getting hitched. I am constantly surprised by folks bringing these things up after they got married. You should know their value system regarding important subjects so you know if you complement each other. Some of these big questions might be:

Do you want children? This is one of the biggest and most important choices you will face as a couple.

Where do you want to live? City or country? East Coast or West Coast? Abroad or at home? Her country or your country?

What’s your relationship with money and finances? Some people are spenders, and some people are savers. Neither is wrong, but incompatible views on money can be one of the biggest conflict areas in a relationship.

How does faith play a role? What’s your belief system or religion and are you OK with hers? If you have kids, are you going to raise them in a particular faith? If so, which one?

hunt quote
Make sure you know your partner’s core values and desires before you propose.

How will work vs. home go? Do you see yourself both still working? Or maybe one person will become the primary caregiver while the other does the lion’s share of bringing home the bacon. How would childcare work?

What are your overall health and fitness goals? If one person is a gym rat and another likes to stay in and chill, that can cause resentment in a relationship. Do you like the same foods? Can you cook together? Does one person do more of the food prep or cleaning?

Do your libidos match? One of the biggest things I see that can affect relationships is mismatched sex drives. You may think it’s not a big deal in the beginning, but it’s something that can really affect the mood of a couple. If one person feels as if he or she is constantly badgering the other person for sex, it can start to build resentment and frustration. If you do have differing drives, how are you going to handle that in the future?

How Do I Propose?

Okay, you’ve realized that you want to spend the rest of your life with her. Now, how do you go about asking her to spend the rest of her life with you? First off, there is no right way of doing it, and proposals look different for everyone, so take everything and adapt it to what works best for you.

Make a Plan!

“The proposal is a ‘story’ that the two of you will share with others way into the future.” says Dr. Terri Orbuch author of “5 Simple Steps to Take Your Marriage From Good to Great,” exclusively to DatingAdvice. “Make sure you plan ahead so that she/the two of you have a ‘story’ to share that is meaningful and special. In addition, include a special place or something special to her in the proposal itself. For example, if she likes nature, you may want to ask her out on a nature trail. If you first met at a special restaurant, you may want to propose at the restaurant where you met or had your first date. The words (what you will specifically say), how, where, and what to include in the proposal takes planning.”

hunt quote-- make plans for your proposal
Don’t stumble your way through a proposal– make a plan in advance.

It Doesn’t Need to be a Surprise

While is nice for the actual proposal to be a surprise, the thought of getting married should not be surprising. This is something that most couples discuss beforehand. Do you know what her thoughts on marriage are? How about her thoughts about marriage with you? In my opinion, she should be aware that you want to marry her and that a proposal may be coming soon!

Know Her Expectations

“It is important to identify your partner’s expectations about the proposal and all that it entails,” continued Dr. Terri, who is also a therapist, dating and relationship coach, and professor at Oakland University in Michigan.

hunt quote about meeting proposal expectations
Women often have expectations about how their proposal should go down.

“That doesn’t mean the proposal will be less surprising or romantic, it just means that she is more likely to be happy and satisfied with the proposal (and all it entails). Women often have specific expectations (read: statements or ideas about how it should go and where) and if you want to ensure that she is happy and satisfied (and will say yes), you want to try and meet those expectations.”

Some women might want a public proposal with friends and family around. Others might want it in a quiet, personal moment.  

And Don’t Forget to Keep the Ring Safe! 

I know personally that once you have that ring, it burns a hole in your pocket! You touch it, you’re worried about it, you keep looking at it, you might show your friends, etc. This ring is not only (probably) very expensive but also has many emotions tied up around it. Don’t let anything happen to it.

If it’s going to be a bit, hide it somewhere super safe, and don’t mess around with it. Also, Be very careful with your proposal if there’s water around or anything else that can make the ring disappear.

Finally, congratulations on getting this far in a relationship! Let me tell you, when you find the right person, you can’t WAIT to spend the rest of your life with them.