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How You Will Know When It's the Right Time To Propose

6 min read

How You Will Know When It's the Right Time To Propose

Knowing when to propose - the most important moment in every guy’s life, isn’t always easy to figure out. No matter how long you’ve been together, the question of whether or not to propose will come up at some point. And no question causes more doubt or anxiety than this one.

There’s no hard and fast rule as to when should a man propose. There are, however, sure signs that tell you you’re ready. If you’re asking yourself, “when is the right time to propose?”, we’ve put together a list of the top 15 signs that tell you the time has come to pop the question.


1. You Talk About “We” and Not “I”

Do you catch yourself saying “we’re great” when someone asks how you, and just you, are doing? Or do you sprinkle in references to “us” and “we” in general conversation, even if not strictly necessary?

If you haven’t noticed yourself doing this, look out for it. Your general desire to talk about “us” shows that your thinking has expanded beyond just you, which is a great clue that you might be ready for marriage.

2. You’ve Reached a Milestone

Many couples agree that they won’t get married until they get a promotion, until they finish their masters, or until they have enough money saved for a down payment on a house. In general, reaching some form of financial stability is a milestone that might mean you’re ready to put a ring on it, even if you’ve never verbalized this to your partner.

On the flip side, we’re not saying you have to have your entire life figured out and the job of your dreams to propose, but you should have everything more or less together. And sometimes reaching a milestone is precisely how to know when to propose.



3. You’ve Lived Together for a While

Sharing space and dealing with the realities of everyday life is a non-negotiable prerequisite to marriage. Seriously, if you’re thinking of marrying someone you haven’t lived with, consider this a warning that that’s a bad idea. Don’t do it.

But if you have been living together for a while, and it’s going well, that’s another sign that the answer to the all-important question of “how do you know when to propose?” is that you’re probably ready. After all, now you know that your partner doesn’t leave their dirty dishes in the sink for weeks on end, and that’s pretty important in our book.


4. She’s Dropping Hints

Part of getting engaged is figuring out if you’re ready, but when you ask her to marry you, you’re going to want her to be prepared, too. When she’s dropping hints left and right, you’ll know when to propose. That’s right. If she mentions getting engaged regularly, it’s because she wants you to ask her to marry you.

Trust us. She’s not doing it to be cute. Consider this your number one sign that she’s ready to get married. You’re welcome.

5. You Can’t Imagine Being Single

Many guys know when to pop the question when they realize that they don’t miss their bachelor days. Not being able to imagine being single is a great way to know whether you’re ready for marriage. It means you think that what you have is way better than anything you could find.

6. You Know Each Other’s Financial Situation

“When should I propose to my girlfriend?” you ask, and the answer is that if you don’t know about their financial situation, you’re not ready. Yeah, we know, this isn’t romantic at all, but knowing when to propose means getting up close and personal … with your S.O.’s financials.

After all, when you get married, their debt becomes your debt. If your girlfriend’s got some skeletons in the closet, it’s best to find out before you sign that marriage license. Because there are some things that love can’t conquer, and credit card addiction is one of them.


7. Your Family Supports Your Relationship

When a guy is asking, “Should I propose to her?” he should also be asking what his family thinks of his relationship. We get it, your family’s opinion shouldn’t be the end all be all, but if your family has reservations about you walking down the aisle, they may be worth paying attention to.

The support of your friends is also worth looking at. If all your friends can’t stand your significant other, holy matrimony might not be the best path for you to go down.

8. You’ve Talked About the Future … Together

Okay, this might seem obvious, but one way to know if you’re ready to pop the question is if you talk about the things you’re going to do together, we’re talking years down the road, not just next weekend. Discussing shared goals, plans, and dreams is a pretty good indicator that she’s ready to make a long-term commitment.

9. You’re on the Same Page About Kids

If you’re asking, “When should I ask her to marry me?” the answer is definitely … when you’ve discussed kids. And when you know you’re on the same page about kids.

It doesn’t matter whether you want to have them or not. It’s critical that you two want the same things. Being a parent is a life-defining decision, and if you don’t agree on whether or not to embark on this great journey, you’re setting yourself up for a life of frustration, anger, and resentment.

Don’t say we didn’t warn you.


10. You Know What Her Career/Life Goals Are

Another thing to ask yourself when you’re wondering “should I propose” is whether or not you know what her career and life goals are. You should have a pretty good idea of what she wants to accomplish in life, and not only that, your goals should be more or less aligned.

We’re not saying that you need to be on the same career path, but a shared trajectory is essential.

11. You’ve Gone on Vacation Together

Going on vacation together may seem banal but trust us, taking a trip is almost as crucial a prerequisite to marriage as living together.

Why, you ask? Believe it or not, it’s actually pretty easy to get along with someone when you both spend the majority of the day working and possibly doing other things in the evening. The real compatibility test comes when you have all day to spend with them on vacation.

Vacation reveals important things. Do you gravitate toward the same activities when you’re away? Do you fight? Does this person make any place feel amazing, even if it isn’t? If you get along on vacation, your relationship chances look good.

12. There’s Nothing About Her You Want to Change

You love her just the way she is. You couldn’t imagine anything about her being even better than it already is. You know what you’re getting, and you are one satisfied customer. Because there’s no greater recipe for disaster than marrying someone you hope to change.


13. You Know Her Family

It’s not always easy to know when the right time is to propose to your girlfriend, but one thing is clear: you should have some relationship with her family.

Not only does her family have a profound influence on who she is, if you marry her, you’re also marrying them, too. If you can’t stand her family, or if they don’t accept you, these are serious red flags when it comes to marriage. 

14. You’ve Found Someone Who Supports You

When should you propose? When you’ve found someone who’s your greatest cheerleader. Someone who you call first when something important happens to you, good or bad. Someone who’s a shoulder to cry on. Someone who will drop anything to be there for you. That’s when you should propose.


15. You Can’t Picture Your Life Without Her

When asking yourself, “When should I propose?” the most important question might be this one. Can you picture your life without her? Do you want to live your life without her? The answer to both of these questions should be a resounding no. If you’re on the fence, it’s probably not meant to be.

Now That You Know the Best Time to Propose

It’s time to start thinking ahead! What comes after your engagement? You’ll soon find out that figuring out when to propose was the easy part.

Start thinking about your groomsmen ASAP, and by that we mean start thinking about what to get them. That’s right, a cool gift for your groomsmen is non-negotiable, which is why getting a jump on your groomsmen gifts should be a top priority. Lucky for you we’ve got a ton of best man gift ideas to help you out.

We recommend checking out Swanky Badger’s collection of unique, personalized gifts for all your groomsmen and best man gift needs. From watches that stand out to hip flasks for your bachelor party, Swanky Badger makes gifts that make a real statement.   


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