Family

Getting Engaged: Tips for Making the Most of Your Special Moment

Stephanie Booth

|

May 2, 2023

Trustworthy is an intelligent digital vault that protects and optimizes your family's information so that you can save time, money, and enjoy peace of mind.

The intelligent digital vault for families

Trustworthy protects and optimizes important family information so you can save time, money, and enjoy peace of mind

Falling in love can happen quickly, but asking someone to spend their life with you  is often a more gradual decision. After all, you’re not only committing to sharing your living space, but your families, finances, and legal obligations, not to mention each other’s embarrassing quirks. (Don’t worry — they make you that much more endearing!) 

In this Guide, we explain how to make the most of getting engaged.

Key Takeaways:

  • How to know — like, really know — that you’re ready for marriage

  • When and how to propose (and how to announce your engagement)

  • What to expect after you get engaged and before the wedding 

Download the Getting Married Checklist

Am I ready to get married?

It’s satisfying when questions have a definite answer. Does the sun come up every morning? (Yes.) Is the color orange a mix of red and yellow? (Also yes.) And 2+2, of course, is 4. 

The concept of love is nowhere near as precise. Although it’s one of the most significant emotions we experience as humans, love is notoriously hard to define. For instance, is it a cultural phenomenon? Or a physical drive, akin to hunger and thirst? That depends on the scientist you ask.

Fortunately, experts do seem to largely agree on the signs that you’re ready to get engaged. They include:

Getting engaged doesn't feel scary

It’s common to feel butterflies around any big life decision. When something momentous is about to happen, it’s only human for emotions to run high. But ideally, the idea of getting engaged should make you feel more thrilled than scared. 

You might ask yourself: Am I excited to get married to this particular person? Can I see myself growing old with them? Do they bring out the best in me? If you’ve met “the one,” your answers should be pretty clear, even if you’re still experiencing some anxiety.)

You’ve made it through some rough patches

Surprisingly, “We’ve never had a fight” isn’t always a good thing! (Even for the conflict-averse.) Having disagreements and being able to talk through them is an important skill for married couples. Life is full of challenges and irritations. You want to have a sense that you and your partner can weather storms before they actually happen.

And if the flip side is true — that you and your significant other have already hit lots of rough patches together — you may want to dig deeper into that, as well. Are your communication skills in sync? Are your disagreements respectful? Do you learn about each other when you fight and come out stronger on the other side? 

You’ve discussed life and family goals with your partner and are on the same page

Of course, you and your partner both want to be happy. But what else do you specifically want? For instance, are you on the same page about owning pets? Having kids? Do you want to live in a city or in a rural area? Do you both have the same philosophies about work-life balance?

It’s important to talk about career, financial, and relationship goals before your engagement. Although your priorities will change and grow through the years, you’ll find it easier to support each other right from the start.

(And if you’re a dog lover and they’re highly allergic, that’s a great thing to sort out before you’re married.)

Plan the proposal

Wedding proposals don’t have to be extravagant. They only need to be heartfelt. Swept up in a particular moment and want to spontaneously ask your significant other to marry you? Perfect. But according to a survey by The Knot, nearly 90 percent of people plan out wedding proposals. (And 42 percent spend up to four months crafting their idea.)

Here’s what that timeline could look like:

  • Think about a proposal that fits.

    Proposing is an art form. Instagram and Pinterest can provide endless inspiration, but really think about what your partner would love. What makes them happy? What meaningful rituals, traditions, or jokes do you share?

  • Decide who else should be there.

    Do you want to invite close friends? Family members? Would you like to hire professionals to document the moment with videos or photography? What about a musician or even a celebrity to make an appearance? Iron out the logistics ahead of time. If your dream is a flash mob proposal set to Bruno Mars’ “Marry Me,” give those dancers time to learn the choreography.

  • Rehearse!

    Once you know where the proposing will happen, you can work on the how. Keeping it simple is just fine. (The same Knot survey found that 86% of people stick with the traditional phrase, “Will you marry me?”) But you still want to get your presentation just right.

    To curb in-the-moment jitters, practice what you’ll say, and even where you’ll stand and what you’ll wear. It sounds counter-intuitive, but the more you rehearse, the more natural your proposal will feel.

  • Go easy on yourself.

    Proposing doesn’t have to be a total surprise. If a secret is spilled, plans are leaked, or you find that you need your partner’s input or approval for something ahead of time, all is not lost. They can still be overjoyed at the thoughtful moment that you’re putting together just for them.

Shop for a ring

Engagement rings date back to 200 B.C., when Ancient Roman women wore them to signify a business contract or…obedience. Luckily, much has changed since then — including the fact that 62 percent of people in relationships now shop together for that special ring. 

Doing so can prevent some thorny etiquette issues, like what to do if the ring doesn’t fit or your partner wishes you’d chosen another design.

What should I consider when choosing an engagement ring?

Keep in mind:

How much can you comfortably spend?

It’s a myth that an engagement ring should cost three months of your salary. The truth is that you should choose a ring that fits comfortably within your budget. Job security, student loans, credit card debts, hoping to save for a new home or special honeymoon — these are all legitimate reasons to carefully budget how much you spend on a ring.

Which design do you want?

If you’d like a diamond engagement ring, determine the shape first. A round diamond is the most traditional, but you have plenty of statement-making choices, including emerald, princess, and radiant-cut.

Next, decide on the size. Are you willing to sacrifice carat count for clarity? The larger the diamond, the costlier the ring. (Surprisingly, you may also be able to save money by choosing a diamond in a less common weight — such as a .92-carat diamond instead of a 1-carat diamond.)

Finally, choose a band. Gold is always a popular choice, but white gold, rose gold, silver, and titanium are options as well. 

Choosing an engagement ring can be a lengthy process — and an investment. Make sure your stone is certified by an accredited grading laboratory like the American Gem Society or International Gemological Institute. 

If so, you’ll receive a diamond certificate, a detailed document that describes and verifies your stone’s characteristics. (This is different from an appraisal or valuation certificate, which estimates the value of the ring for insurance purposes.) 

Once you have these documents, consider uploading them to Trustworthy’s Family Operating System®. Not only will you know exactly where this information is when you need it, but we’re the only online service that exceeds industry standards for security and privacy.

Propose marriage

The moment’s arrived to pop the question! And maybe you didn’t rehearse, or you forgot your index cards, or at the last minute, you canceled the flash mob because it just seemed too Instagram-perfect.

What now? 

  • Trust your instincts

    Let your emotions guide what you say.

  • Let your partner know what you love about them. 

    Be specific. If you love how they sewed a Christmas tree costume for your cat — and coaxed them to wear it —  call that out. 

  • Give a big picture view. 

    What happened when you two first met? Where are you now in your relationship, and how has it changed you for the better?

  • Look to the future. 

    Where do you two go from here? Share your hopes for the many years ahead. 

After that, it’s the perfect time to pop the question.

Announce your engagement

When it’s time to celebrate and share your happy news, consider following some traditional wedding etiquette:

  • Tell your inner circle first. 

    Start with your closest family members and friends, then spread the word from there.

  • Post on social media. 

    Upload that lovely engagement photo or video so everyone can share in your special moment (and hear all about the planning that went into it!)

  • Send out an announcement via snail mail. 

    An engagement is often announced by someone other than the couple, like the parent(s) who will host the wedding, but you can certainly announce your own happy news!

As you move towards the marriage ceremony, you’ll have lots of other fun details to attend to — like the color of your bridesmaid dresses and if you want a destination wedding. But deep down, under all its romantic trappings, marriage is a legal construct. In the months ahead, be prepared to complete some paperwork that will entail your drivers license or passport, social security card, birth certificate, and a divorce or death decree if either you or your partner have previously been married. 

Instead of making a checklist of the documents you need and where they’re kept, think about signing up for Trustworthy’s Family Operating System®. We’re the only platform that gives you a centralized view of all your important information. An easy-to-use guided workflow helps you easily gather information, and all major file types and media are supported. You and your partner will be able to share information whenever you need, and sync information instantly between your computers, phones, and tablets.

Trustworthy is also great for multi-households. For instance, if you’re blending families through your marriage, it can give you the ability to connect with an unlimited number of additional households from your account — and seamlessly manage information and navigate between them. (You and your family members will also get a personalized onboarding session.)

Getting engaged is an exciting, busy journey. Trustworthy can help you stay organized along the way.

Family

Getting Engaged: Tips for Making the Most of Your Special Moment

Stephanie Booth

|

May 2, 2023

Trustworthy is an intelligent digital vault that protects and optimizes your family's information so that you can save time, money, and enjoy peace of mind.

Falling in love can happen quickly, but asking someone to spend their life with you  is often a more gradual decision. After all, you’re not only committing to sharing your living space, but your families, finances, and legal obligations, not to mention each other’s embarrassing quirks. (Don’t worry — they make you that much more endearing!) 

In this Guide, we explain how to make the most of getting engaged.

Key Takeaways:

  • How to know — like, really know — that you’re ready for marriage

  • When and how to propose (and how to announce your engagement)

  • What to expect after you get engaged and before the wedding 

Download the Getting Married Checklist

Am I ready to get married?

It’s satisfying when questions have a definite answer. Does the sun come up every morning? (Yes.) Is the color orange a mix of red and yellow? (Also yes.) And 2+2, of course, is 4. 

The concept of love is nowhere near as precise. Although it’s one of the most significant emotions we experience as humans, love is notoriously hard to define. For instance, is it a cultural phenomenon? Or a physical drive, akin to hunger and thirst? That depends on the scientist you ask.

Fortunately, experts do seem to largely agree on the signs that you’re ready to get engaged. They include:

Getting engaged doesn't feel scary

It’s common to feel butterflies around any big life decision. When something momentous is about to happen, it’s only human for emotions to run high. But ideally, the idea of getting engaged should make you feel more thrilled than scared. 

You might ask yourself: Am I excited to get married to this particular person? Can I see myself growing old with them? Do they bring out the best in me? If you’ve met “the one,” your answers should be pretty clear, even if you’re still experiencing some anxiety.)

You’ve made it through some rough patches

Surprisingly, “We’ve never had a fight” isn’t always a good thing! (Even for the conflict-averse.) Having disagreements and being able to talk through them is an important skill for married couples. Life is full of challenges and irritations. You want to have a sense that you and your partner can weather storms before they actually happen.

And if the flip side is true — that you and your significant other have already hit lots of rough patches together — you may want to dig deeper into that, as well. Are your communication skills in sync? Are your disagreements respectful? Do you learn about each other when you fight and come out stronger on the other side? 

You’ve discussed life and family goals with your partner and are on the same page

Of course, you and your partner both want to be happy. But what else do you specifically want? For instance, are you on the same page about owning pets? Having kids? Do you want to live in a city or in a rural area? Do you both have the same philosophies about work-life balance?

It’s important to talk about career, financial, and relationship goals before your engagement. Although your priorities will change and grow through the years, you’ll find it easier to support each other right from the start.

(And if you’re a dog lover and they’re highly allergic, that’s a great thing to sort out before you’re married.)

Plan the proposal

Wedding proposals don’t have to be extravagant. They only need to be heartfelt. Swept up in a particular moment and want to spontaneously ask your significant other to marry you? Perfect. But according to a survey by The Knot, nearly 90 percent of people plan out wedding proposals. (And 42 percent spend up to four months crafting their idea.)

Here’s what that timeline could look like:

  • Think about a proposal that fits.

    Proposing is an art form. Instagram and Pinterest can provide endless inspiration, but really think about what your partner would love. What makes them happy? What meaningful rituals, traditions, or jokes do you share?

  • Decide who else should be there.

    Do you want to invite close friends? Family members? Would you like to hire professionals to document the moment with videos or photography? What about a musician or even a celebrity to make an appearance? Iron out the logistics ahead of time. If your dream is a flash mob proposal set to Bruno Mars’ “Marry Me,” give those dancers time to learn the choreography.

  • Rehearse!

    Once you know where the proposing will happen, you can work on the how. Keeping it simple is just fine. (The same Knot survey found that 86% of people stick with the traditional phrase, “Will you marry me?”) But you still want to get your presentation just right.

    To curb in-the-moment jitters, practice what you’ll say, and even where you’ll stand and what you’ll wear. It sounds counter-intuitive, but the more you rehearse, the more natural your proposal will feel.

  • Go easy on yourself.

    Proposing doesn’t have to be a total surprise. If a secret is spilled, plans are leaked, or you find that you need your partner’s input or approval for something ahead of time, all is not lost. They can still be overjoyed at the thoughtful moment that you’re putting together just for them.

Shop for a ring

Engagement rings date back to 200 B.C., when Ancient Roman women wore them to signify a business contract or…obedience. Luckily, much has changed since then — including the fact that 62 percent of people in relationships now shop together for that special ring. 

Doing so can prevent some thorny etiquette issues, like what to do if the ring doesn’t fit or your partner wishes you’d chosen another design.

What should I consider when choosing an engagement ring?

Keep in mind:

How much can you comfortably spend?

It’s a myth that an engagement ring should cost three months of your salary. The truth is that you should choose a ring that fits comfortably within your budget. Job security, student loans, credit card debts, hoping to save for a new home or special honeymoon — these are all legitimate reasons to carefully budget how much you spend on a ring.

Which design do you want?

If you’d like a diamond engagement ring, determine the shape first. A round diamond is the most traditional, but you have plenty of statement-making choices, including emerald, princess, and radiant-cut.

Next, decide on the size. Are you willing to sacrifice carat count for clarity? The larger the diamond, the costlier the ring. (Surprisingly, you may also be able to save money by choosing a diamond in a less common weight — such as a .92-carat diamond instead of a 1-carat diamond.)

Finally, choose a band. Gold is always a popular choice, but white gold, rose gold, silver, and titanium are options as well. 

Choosing an engagement ring can be a lengthy process — and an investment. Make sure your stone is certified by an accredited grading laboratory like the American Gem Society or International Gemological Institute. 

If so, you’ll receive a diamond certificate, a detailed document that describes and verifies your stone’s characteristics. (This is different from an appraisal or valuation certificate, which estimates the value of the ring for insurance purposes.) 

Once you have these documents, consider uploading them to Trustworthy’s Family Operating System®. Not only will you know exactly where this information is when you need it, but we’re the only online service that exceeds industry standards for security and privacy.

Propose marriage

The moment’s arrived to pop the question! And maybe you didn’t rehearse, or you forgot your index cards, or at the last minute, you canceled the flash mob because it just seemed too Instagram-perfect.

What now? 

  • Trust your instincts

    Let your emotions guide what you say.

  • Let your partner know what you love about them. 

    Be specific. If you love how they sewed a Christmas tree costume for your cat — and coaxed them to wear it —  call that out. 

  • Give a big picture view. 

    What happened when you two first met? Where are you now in your relationship, and how has it changed you for the better?

  • Look to the future. 

    Where do you two go from here? Share your hopes for the many years ahead. 

After that, it’s the perfect time to pop the question.

Announce your engagement

When it’s time to celebrate and share your happy news, consider following some traditional wedding etiquette:

  • Tell your inner circle first. 

    Start with your closest family members and friends, then spread the word from there.

  • Post on social media. 

    Upload that lovely engagement photo or video so everyone can share in your special moment (and hear all about the planning that went into it!)

  • Send out an announcement via snail mail. 

    An engagement is often announced by someone other than the couple, like the parent(s) who will host the wedding, but you can certainly announce your own happy news!

As you move towards the marriage ceremony, you’ll have lots of other fun details to attend to — like the color of your bridesmaid dresses and if you want a destination wedding. But deep down, under all its romantic trappings, marriage is a legal construct. In the months ahead, be prepared to complete some paperwork that will entail your drivers license or passport, social security card, birth certificate, and a divorce or death decree if either you or your partner have previously been married. 

Instead of making a checklist of the documents you need and where they’re kept, think about signing up for Trustworthy’s Family Operating System®. We’re the only platform that gives you a centralized view of all your important information. An easy-to-use guided workflow helps you easily gather information, and all major file types and media are supported. You and your partner will be able to share information whenever you need, and sync information instantly between your computers, phones, and tablets.

Trustworthy is also great for multi-households. For instance, if you’re blending families through your marriage, it can give you the ability to connect with an unlimited number of additional households from your account — and seamlessly manage information and navigate between them. (You and your family members will also get a personalized onboarding session.)

Getting engaged is an exciting, busy journey. Trustworthy can help you stay organized along the way.

Family

Getting Engaged: Tips for Making the Most of Your Special Moment

Stephanie Booth

|

May 2, 2023

Trustworthy is an intelligent digital vault that protects and optimizes your family's information so that you can save time, money, and enjoy peace of mind.

The intelligent digital vault for families

Trustworthy protects and optimizes important family information so you can save time, money, and enjoy peace of mind

Falling in love can happen quickly, but asking someone to spend their life with you  is often a more gradual decision. After all, you’re not only committing to sharing your living space, but your families, finances, and legal obligations, not to mention each other’s embarrassing quirks. (Don’t worry — they make you that much more endearing!) 

In this Guide, we explain how to make the most of getting engaged.

Key Takeaways:

  • How to know — like, really know — that you’re ready for marriage

  • When and how to propose (and how to announce your engagement)

  • What to expect after you get engaged and before the wedding 

Download the Getting Married Checklist

Am I ready to get married?

It’s satisfying when questions have a definite answer. Does the sun come up every morning? (Yes.) Is the color orange a mix of red and yellow? (Also yes.) And 2+2, of course, is 4. 

The concept of love is nowhere near as precise. Although it’s one of the most significant emotions we experience as humans, love is notoriously hard to define. For instance, is it a cultural phenomenon? Or a physical drive, akin to hunger and thirst? That depends on the scientist you ask.

Fortunately, experts do seem to largely agree on the signs that you’re ready to get engaged. They include:

Getting engaged doesn't feel scary

It’s common to feel butterflies around any big life decision. When something momentous is about to happen, it’s only human for emotions to run high. But ideally, the idea of getting engaged should make you feel more thrilled than scared. 

You might ask yourself: Am I excited to get married to this particular person? Can I see myself growing old with them? Do they bring out the best in me? If you’ve met “the one,” your answers should be pretty clear, even if you’re still experiencing some anxiety.)

You’ve made it through some rough patches

Surprisingly, “We’ve never had a fight” isn’t always a good thing! (Even for the conflict-averse.) Having disagreements and being able to talk through them is an important skill for married couples. Life is full of challenges and irritations. You want to have a sense that you and your partner can weather storms before they actually happen.

And if the flip side is true — that you and your significant other have already hit lots of rough patches together — you may want to dig deeper into that, as well. Are your communication skills in sync? Are your disagreements respectful? Do you learn about each other when you fight and come out stronger on the other side? 

You’ve discussed life and family goals with your partner and are on the same page

Of course, you and your partner both want to be happy. But what else do you specifically want? For instance, are you on the same page about owning pets? Having kids? Do you want to live in a city or in a rural area? Do you both have the same philosophies about work-life balance?

It’s important to talk about career, financial, and relationship goals before your engagement. Although your priorities will change and grow through the years, you’ll find it easier to support each other right from the start.

(And if you’re a dog lover and they’re highly allergic, that’s a great thing to sort out before you’re married.)

Plan the proposal

Wedding proposals don’t have to be extravagant. They only need to be heartfelt. Swept up in a particular moment and want to spontaneously ask your significant other to marry you? Perfect. But according to a survey by The Knot, nearly 90 percent of people plan out wedding proposals. (And 42 percent spend up to four months crafting their idea.)

Here’s what that timeline could look like:

  • Think about a proposal that fits.

    Proposing is an art form. Instagram and Pinterest can provide endless inspiration, but really think about what your partner would love. What makes them happy? What meaningful rituals, traditions, or jokes do you share?

  • Decide who else should be there.

    Do you want to invite close friends? Family members? Would you like to hire professionals to document the moment with videos or photography? What about a musician or even a celebrity to make an appearance? Iron out the logistics ahead of time. If your dream is a flash mob proposal set to Bruno Mars’ “Marry Me,” give those dancers time to learn the choreography.

  • Rehearse!

    Once you know where the proposing will happen, you can work on the how. Keeping it simple is just fine. (The same Knot survey found that 86% of people stick with the traditional phrase, “Will you marry me?”) But you still want to get your presentation just right.

    To curb in-the-moment jitters, practice what you’ll say, and even where you’ll stand and what you’ll wear. It sounds counter-intuitive, but the more you rehearse, the more natural your proposal will feel.

  • Go easy on yourself.

    Proposing doesn’t have to be a total surprise. If a secret is spilled, plans are leaked, or you find that you need your partner’s input or approval for something ahead of time, all is not lost. They can still be overjoyed at the thoughtful moment that you’re putting together just for them.

Shop for a ring

Engagement rings date back to 200 B.C., when Ancient Roman women wore them to signify a business contract or…obedience. Luckily, much has changed since then — including the fact that 62 percent of people in relationships now shop together for that special ring. 

Doing so can prevent some thorny etiquette issues, like what to do if the ring doesn’t fit or your partner wishes you’d chosen another design.

What should I consider when choosing an engagement ring?

Keep in mind:

How much can you comfortably spend?

It’s a myth that an engagement ring should cost three months of your salary. The truth is that you should choose a ring that fits comfortably within your budget. Job security, student loans, credit card debts, hoping to save for a new home or special honeymoon — these are all legitimate reasons to carefully budget how much you spend on a ring.

Which design do you want?

If you’d like a diamond engagement ring, determine the shape first. A round diamond is the most traditional, but you have plenty of statement-making choices, including emerald, princess, and radiant-cut.

Next, decide on the size. Are you willing to sacrifice carat count for clarity? The larger the diamond, the costlier the ring. (Surprisingly, you may also be able to save money by choosing a diamond in a less common weight — such as a .92-carat diamond instead of a 1-carat diamond.)

Finally, choose a band. Gold is always a popular choice, but white gold, rose gold, silver, and titanium are options as well. 

Choosing an engagement ring can be a lengthy process — and an investment. Make sure your stone is certified by an accredited grading laboratory like the American Gem Society or International Gemological Institute. 

If so, you’ll receive a diamond certificate, a detailed document that describes and verifies your stone’s characteristics. (This is different from an appraisal or valuation certificate, which estimates the value of the ring for insurance purposes.) 

Once you have these documents, consider uploading them to Trustworthy’s Family Operating System®. Not only will you know exactly where this information is when you need it, but we’re the only online service that exceeds industry standards for security and privacy.

Propose marriage

The moment’s arrived to pop the question! And maybe you didn’t rehearse, or you forgot your index cards, or at the last minute, you canceled the flash mob because it just seemed too Instagram-perfect.

What now? 

  • Trust your instincts

    Let your emotions guide what you say.

  • Let your partner know what you love about them. 

    Be specific. If you love how they sewed a Christmas tree costume for your cat — and coaxed them to wear it —  call that out. 

  • Give a big picture view. 

    What happened when you two first met? Where are you now in your relationship, and how has it changed you for the better?

  • Look to the future. 

    Where do you two go from here? Share your hopes for the many years ahead. 

After that, it’s the perfect time to pop the question.

Announce your engagement

When it’s time to celebrate and share your happy news, consider following some traditional wedding etiquette:

  • Tell your inner circle first. 

    Start with your closest family members and friends, then spread the word from there.

  • Post on social media. 

    Upload that lovely engagement photo or video so everyone can share in your special moment (and hear all about the planning that went into it!)

  • Send out an announcement via snail mail. 

    An engagement is often announced by someone other than the couple, like the parent(s) who will host the wedding, but you can certainly announce your own happy news!

As you move towards the marriage ceremony, you’ll have lots of other fun details to attend to — like the color of your bridesmaid dresses and if you want a destination wedding. But deep down, under all its romantic trappings, marriage is a legal construct. In the months ahead, be prepared to complete some paperwork that will entail your drivers license or passport, social security card, birth certificate, and a divorce or death decree if either you or your partner have previously been married. 

Instead of making a checklist of the documents you need and where they’re kept, think about signing up for Trustworthy’s Family Operating System®. We’re the only platform that gives you a centralized view of all your important information. An easy-to-use guided workflow helps you easily gather information, and all major file types and media are supported. You and your partner will be able to share information whenever you need, and sync information instantly between your computers, phones, and tablets.

Trustworthy is also great for multi-households. For instance, if you’re blending families through your marriage, it can give you the ability to connect with an unlimited number of additional households from your account — and seamlessly manage information and navigate between them. (You and your family members will also get a personalized onboarding session.)

Getting engaged is an exciting, busy journey. Trustworthy can help you stay organized along the way.

Family

Getting Engaged: Tips for Making the Most of Your Special Moment

Stephanie Booth

|

May 2, 2023

Trustworthy is an intelligent digital vault that protects and optimizes your family's information so that you can save time, money, and enjoy peace of mind.

The intelligent digital vault for families

Trustworthy protects and optimizes important family information so you can save time, money, and enjoy peace of mind

Falling in love can happen quickly, but asking someone to spend their life with you  is often a more gradual decision. After all, you’re not only committing to sharing your living space, but your families, finances, and legal obligations, not to mention each other’s embarrassing quirks. (Don’t worry — they make you that much more endearing!) 

In this Guide, we explain how to make the most of getting engaged.

Key Takeaways:

  • How to know — like, really know — that you’re ready for marriage

  • When and how to propose (and how to announce your engagement)

  • What to expect after you get engaged and before the wedding 

Download the Getting Married Checklist

Am I ready to get married?

It’s satisfying when questions have a definite answer. Does the sun come up every morning? (Yes.) Is the color orange a mix of red and yellow? (Also yes.) And 2+2, of course, is 4. 

The concept of love is nowhere near as precise. Although it’s one of the most significant emotions we experience as humans, love is notoriously hard to define. For instance, is it a cultural phenomenon? Or a physical drive, akin to hunger and thirst? That depends on the scientist you ask.

Fortunately, experts do seem to largely agree on the signs that you’re ready to get engaged. They include:

Getting engaged doesn't feel scary

It’s common to feel butterflies around any big life decision. When something momentous is about to happen, it’s only human for emotions to run high. But ideally, the idea of getting engaged should make you feel more thrilled than scared. 

You might ask yourself: Am I excited to get married to this particular person? Can I see myself growing old with them? Do they bring out the best in me? If you’ve met “the one,” your answers should be pretty clear, even if you’re still experiencing some anxiety.)

You’ve made it through some rough patches

Surprisingly, “We’ve never had a fight” isn’t always a good thing! (Even for the conflict-averse.) Having disagreements and being able to talk through them is an important skill for married couples. Life is full of challenges and irritations. You want to have a sense that you and your partner can weather storms before they actually happen.

And if the flip side is true — that you and your significant other have already hit lots of rough patches together — you may want to dig deeper into that, as well. Are your communication skills in sync? Are your disagreements respectful? Do you learn about each other when you fight and come out stronger on the other side? 

You’ve discussed life and family goals with your partner and are on the same page

Of course, you and your partner both want to be happy. But what else do you specifically want? For instance, are you on the same page about owning pets? Having kids? Do you want to live in a city or in a rural area? Do you both have the same philosophies about work-life balance?

It’s important to talk about career, financial, and relationship goals before your engagement. Although your priorities will change and grow through the years, you’ll find it easier to support each other right from the start.

(And if you’re a dog lover and they’re highly allergic, that’s a great thing to sort out before you’re married.)

Plan the proposal

Wedding proposals don’t have to be extravagant. They only need to be heartfelt. Swept up in a particular moment and want to spontaneously ask your significant other to marry you? Perfect. But according to a survey by The Knot, nearly 90 percent of people plan out wedding proposals. (And 42 percent spend up to four months crafting their idea.)

Here’s what that timeline could look like:

  • Think about a proposal that fits.

    Proposing is an art form. Instagram and Pinterest can provide endless inspiration, but really think about what your partner would love. What makes them happy? What meaningful rituals, traditions, or jokes do you share?

  • Decide who else should be there.

    Do you want to invite close friends? Family members? Would you like to hire professionals to document the moment with videos or photography? What about a musician or even a celebrity to make an appearance? Iron out the logistics ahead of time. If your dream is a flash mob proposal set to Bruno Mars’ “Marry Me,” give those dancers time to learn the choreography.

  • Rehearse!

    Once you know where the proposing will happen, you can work on the how. Keeping it simple is just fine. (The same Knot survey found that 86% of people stick with the traditional phrase, “Will you marry me?”) But you still want to get your presentation just right.

    To curb in-the-moment jitters, practice what you’ll say, and even where you’ll stand and what you’ll wear. It sounds counter-intuitive, but the more you rehearse, the more natural your proposal will feel.

  • Go easy on yourself.

    Proposing doesn’t have to be a total surprise. If a secret is spilled, plans are leaked, or you find that you need your partner’s input or approval for something ahead of time, all is not lost. They can still be overjoyed at the thoughtful moment that you’re putting together just for them.

Shop for a ring

Engagement rings date back to 200 B.C., when Ancient Roman women wore them to signify a business contract or…obedience. Luckily, much has changed since then — including the fact that 62 percent of people in relationships now shop together for that special ring. 

Doing so can prevent some thorny etiquette issues, like what to do if the ring doesn’t fit or your partner wishes you’d chosen another design.

What should I consider when choosing an engagement ring?

Keep in mind:

How much can you comfortably spend?

It’s a myth that an engagement ring should cost three months of your salary. The truth is that you should choose a ring that fits comfortably within your budget. Job security, student loans, credit card debts, hoping to save for a new home or special honeymoon — these are all legitimate reasons to carefully budget how much you spend on a ring.

Which design do you want?

If you’d like a diamond engagement ring, determine the shape first. A round diamond is the most traditional, but you have plenty of statement-making choices, including emerald, princess, and radiant-cut.

Next, decide on the size. Are you willing to sacrifice carat count for clarity? The larger the diamond, the costlier the ring. (Surprisingly, you may also be able to save money by choosing a diamond in a less common weight — such as a .92-carat diamond instead of a 1-carat diamond.)

Finally, choose a band. Gold is always a popular choice, but white gold, rose gold, silver, and titanium are options as well. 

Choosing an engagement ring can be a lengthy process — and an investment. Make sure your stone is certified by an accredited grading laboratory like the American Gem Society or International Gemological Institute. 

If so, you’ll receive a diamond certificate, a detailed document that describes and verifies your stone’s characteristics. (This is different from an appraisal or valuation certificate, which estimates the value of the ring for insurance purposes.) 

Once you have these documents, consider uploading them to Trustworthy’s Family Operating System®. Not only will you know exactly where this information is when you need it, but we’re the only online service that exceeds industry standards for security and privacy.

Propose marriage

The moment’s arrived to pop the question! And maybe you didn’t rehearse, or you forgot your index cards, or at the last minute, you canceled the flash mob because it just seemed too Instagram-perfect.

What now? 

  • Trust your instincts

    Let your emotions guide what you say.

  • Let your partner know what you love about them. 

    Be specific. If you love how they sewed a Christmas tree costume for your cat — and coaxed them to wear it —  call that out. 

  • Give a big picture view. 

    What happened when you two first met? Where are you now in your relationship, and how has it changed you for the better?

  • Look to the future. 

    Where do you two go from here? Share your hopes for the many years ahead. 

After that, it’s the perfect time to pop the question.

Announce your engagement

When it’s time to celebrate and share your happy news, consider following some traditional wedding etiquette:

  • Tell your inner circle first. 

    Start with your closest family members and friends, then spread the word from there.

  • Post on social media. 

    Upload that lovely engagement photo or video so everyone can share in your special moment (and hear all about the planning that went into it!)

  • Send out an announcement via snail mail. 

    An engagement is often announced by someone other than the couple, like the parent(s) who will host the wedding, but you can certainly announce your own happy news!

As you move towards the marriage ceremony, you’ll have lots of other fun details to attend to — like the color of your bridesmaid dresses and if you want a destination wedding. But deep down, under all its romantic trappings, marriage is a legal construct. In the months ahead, be prepared to complete some paperwork that will entail your drivers license or passport, social security card, birth certificate, and a divorce or death decree if either you or your partner have previously been married. 

Instead of making a checklist of the documents you need and where they’re kept, think about signing up for Trustworthy’s Family Operating System®. We’re the only platform that gives you a centralized view of all your important information. An easy-to-use guided workflow helps you easily gather information, and all major file types and media are supported. You and your partner will be able to share information whenever you need, and sync information instantly between your computers, phones, and tablets.

Trustworthy is also great for multi-households. For instance, if you’re blending families through your marriage, it can give you the ability to connect with an unlimited number of additional households from your account — and seamlessly manage information and navigate between them. (You and your family members will also get a personalized onboarding session.)

Getting engaged is an exciting, busy journey. Trustworthy can help you stay organized along the way.

Try Trustworthy today.

Try Trustworthy today.

Try the Family Operating System® for yourself. You (and your family) will love it.

Try the Family Operating System® for yourself. You (and your family) will love it.

No credit card required.

No credit card required.