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Groom 101

Man Down: 10-Step Guide to Proposal Planning & Getting Engaged

Chris Easter man proposing to his girlfriend at sunset

So, you have finally come to your senses and realized she’s the one for you. You want to tie the knot. Get hitched. Join your two households. Whatever you want to call it, the process of proposing can seem like quite the feat, but luckily for you, we’re here to help. From secretly finding her ring size to knowing when to propose, we’re here to ensure the entire process of proposal planning and getting engaged goes as smooth as possible.

When it comes to the future wedding planning, you can leave that almost entirely to your bride-to-be. But when it comes to proposing, the significant task of creating the dream scenario for your relationship and budget is ultimately in your hands.

Whether that means asking her father for permission, deciding to propose in front of friends and family, or setting up an intimate setting for just the two of you, our guide spells it out perfectly for even the most clueless proposer below:

5 Signs She’s Ready For You to Propose

Once you both realize that the relationship is heading towards marriage, something changes. You know you’re going to be proposing, and she knows you’re going to be proposing, but neither of you really know the details — when, where, or how. You’ll probably figure all of these details out as you start to plan a proposal, but let’s be real: planning a proposal is stressful! And then there’s the pressure of finding the perfect ring. Of course, you could just ask her what she likes or offer to take her ring shopping, but if that’s not your (or her style), you’ll need to find out what she loves some other way.

young man proposing to his girlfriend

However, she might have been secretly dropping hints for a while, and you just haven’t noticed! If your girlfriend has done any of the following things, she’s trying to tell you about her perfect engagement ring, without being too obvious.

  1. She’s talking about her friends’ engagement rings

If your girlfriend has been chatting about her other girlfriend’s engagement rings, the temptation to tune out might be strong — but don’t do it! Instead listen up and maybe even prod the conversation along. For example, if she says something like “Ick, (insert friend’s name)’s is so tacky” or “I would never choose (friend name)’s engagement ring” next time she’s checking out Facebook, take notes! Does she hate how big it is? The gold band? The cut of the rock? The more you know what she thinks about her friend’s rings, the more you know about what she likes and doesn’t like.

  1. She’s leaving her magazines open all over the apartment…

On pages that feature engagement rings. You may not be noticing, but if they’re lying open on the couch, on your night stand, or on the kitchen table, check the page — if it’s an engagement ring ad or editorial feature, she’s trying to say something. Especially take note if there are a couple rings circled in Sharpie. Seriously — this happens.

  1. She’s leaving her laptop open…

To her secret engagement ring Pinterest board. For those of you who aren’t familiar with secret Pinterest boards, they’re basically spaces on Pinterest where you can collect photos of stuff you like, without anyone else being able to see them. If you walk into the room with the laptop or computer on a website with pictures of certain engagement rings, remember the link or the name of the ring, and do your research later.

  1. Her BFF or sister is dropping hints

If your girlfriend’s best friend or sister sends you an email or a text offering to help you buy her a ring — her up on it! Chances are, your girlfriend has communicated very clearly to this person what she wants, and they’ll be able to steer you down the right path.

  1. She wakes up and says “I had the best dream that you got me a princess-cut vintage style diamond ring, isn’t that crazy?”

No, that’s not crazy. You should probably set aside some time to go find a ring just like that.

So there you have it — 5 different ways that should tell you that she has a ring in mind, and that you should probably go out and get it before getting engaged!

Engagement Ring Shopping Tips

It isn’t easy making such a large, emotional and financial commitment. Before you go engagement ring shopping, it pays to do some research to make sure you know what to look for and what to expect.

Here’s a quick guide to help keep you on track.

Determine Your Budget

Remember, this isn’t the time to make a hasty decision or impulse buy. Think of this ring as Super Bowl tickets. If you had one chance to pick any seat available, you’d pick the best one you could afford. This may mean staying in one night per weekend, but it’ll be worth it. This ring will be on her finger for the rest of her life. Do yourself a favor and make it count!

Understand the Different Varieties of Engagement Rings

One of the most traditional examples is the diamond solitaire. This ring features a band and a single (or solitaire) diamond. This can be a good way to go if you aren’t sure about her jewelry preferences. This option also offers the most diamond for your dollar, size-wise.

Know the Four C’s

The four most important things to know about a diamond are its cut, color, clarity, and carat weight. You’ll hear all about them during your engagement ring shopping excursions, but it helps to go in with some knowledge. We’ll fill you in on exactly what the four C’s are further down in the guide.

Consider Whether You’ll Also Want to Purchase a Matching Wedding Band

A wedding band is generally a smaller band that is sometimes sold in a set with the engagement ring. Again, this is something you may want to do a little research on before you buy. Talk with your girl. Some women like to have a wedding band while others prefer the engagement ring by itself.

Get the Most For Your Money

Diamond prices vary from store to store as no two diamonds are exactly alike. It pays to do your research and shop around. Go to several of the larger chain stores and price what you want. We then suggest checking out a few smaller mom-and-pop stores.  Pay them a visit and compare prices. You never know where you’re going to find your diamond in the rough.

Research Engagement Ring Insurance

With such a substantial purchase, you’ll definitely want to consider protecting the ring with an insurance plan. The store that you buy from may have an in-house program or you can find a national company that specializes in insuring engagement rings.

TMR Recommendation: Engagement ring shopping is an area where you’ll most likely need some help and that’s perfectly fine. There are many resources you can turn to for guidance. First and foremost, it’s always a good idea to be aware of what type of ring your girl prefers. Knowing her preferences is half the battle. Other people you can seek help with are her best friend, her mother, or if all else fails, one of your groomsmen who has already gone through this process.

The Four C’s

When buying a diamond engagement ring, the first step is to do some research to understand how the quality of a diamond is measured and how it affects pricing. Buying a diamond engagement ring is no simple task. It’s true, and it isn’t exactly cheap either. We’re not one to mince words; you are going to spend a lot on it, but before you do, at least know what it is you need to buy and what’s the best that your budget can get you. Truth-be-told, the hardest aspect of buying an engagement ring is knowing what your bride-to-be prefers.

If you have an idea about what she likes, you can narrow it down by what’s known in the diamond business as the four C’s — clarity, color, cut, and carat.

  1. Clarity – the clearness or purity of a diamond

Technically speaking: Traditionally, a diamond’s quality meant clarity, but in today’s world this is the second most important quality that affects pricing. Clarity is determined by the number, size, nature, and location of any internal inclusions and external blemishes (the number of crystals or clouds that can be seen using 10x magnification).

In regular guy terms:
Let’s be honest, before you stress about being able to afford a flawless diamond, remember that 99.9% of the time you and your fiancé will be looking at the ring with your naked eyes. Unless you’re viewing the diamond with 10x magnification, there really isn’t a noticeable difference. A medium clarity diamond is just as striking as a flawless one.

  1. Color – the amount of color the diamond contains

Technically speaking: The majority of diamonds have a hint of yellow or brown, but a perfect diamond is perfectly transparent with no hue. All diamonds are graded by their comparison to perfect diamonds. So the closer the grade is to D, the closer the diamond is to being perfect.

In regular guy terms: Before you break into a sweat and call off the engagement altogether, remember that the vast majority of diamonds are not perfect. It’s more typical for people to purchase a diamond that’s Grade G or below, but depending on your budget and priorities, Grades D, E, and F are slightly more beautiful diamonds.

4 c's of diamond engagement rings

  1. Cut – the proportions, finish, symmetry, and polish of the diamond

Technically speaking: A diamond’s cut doesn’t actually refer to its shape, but its reflective qualities. A diamond’s angles and finish are what determine its ability to handle light, which creates the sparkling effect that girls love.

When a diamond’s well cut, light enters it and travels to a point where it reflects from one side to the other. It then reflects back out of the diamond and into the observer’s eye, once again, creating the sparkling effect.

Diamond cuts are separated into four categories: ideal cut, very good cut, good cut, and fair-to-poor cut. Because ideal cut diamonds reflect the most amount of light that enters the diamond, they typically sell at a premium, while poorly cut diamonds usually sell at discounted prices.

In regular guy terms: Diamonds with a cut grade of good or very good are the best value with high-quality appeal. Just find out what works best for you and your budget.

  1. Carat – the unit of weight of the diamond

Technically speaking: The value per carat increases exponentially with carat size because larger, rough diamonds occur less frequently than smaller ones. In other words, 2 half-carat diamonds taken together won’t cost as much as 1 one-carat diamond because the one-carat diamond is rarer.

In regular guy terms: Does size really matter? That’s a personal question for each bride. If you’re like most grooms-to-be, your budget makes a difference. Your bride might prefer to have a lower- quality diamond for a larger look, or she might prefer quality over a larger size. It’s up to you to determine her preference.

TMR Recommendation: Diamond engagement and wedding rings are personal to each bride. It’s best to follow this general approach:

  • Establish the budget you can afford. The rule of thumb is to go with the two month’s salary approach. For example, if you make $10,000 per year, you should spend approximately $1,667 on the engagement ring.
  • Be sneaky and determine her preferences on size, quality, and shape on the sly. Or be direct and ask for her opinion; she’ll thank you later.
  • Narrow down the four Cs of a diamond based on:
    1. Her preferences
    2. What your budget will allow
  • Make sure to shop around. The average markup for a diamond ring from a brick and mortar store is 200% to 400%. It pays to do your research!
  • When you’ve narrowed down your selection of diamonds, make sure to ask the jeweler to let you review the independent Diamond Grading Reports, also called certificates. These reports will verify the classification of the four Cs and will help you compare apples to apples.

Should You Go Ring Shopping Together?

Before getting engaged, should you take your girlfriend ring shopping? If you want your proposal to be a total surprise and you already have a good idea about what kind of ring your girlfriend likes (possibly even down to the color, cut and size — turns out you really were listening when she dropped all those hints!), then you can forgo a shopping trip.

But otherwise, taking her ring shopping is a great idea. There are so many options available when it comes to engagement rings. You don’t want to make a completely uneducated guess and risk disappointing her.

young couple ring shopping

Picture this: You get down on one knee with a heart-shaped diamond ring in yellow gold, only to find out later that she wanted a traditional white gold round diamond ring. Awkward… Don’t let this happen to you.

Most likely at this point in your relationship, you both know that marriage is on the horizon, so why not see what ring options are out there ahead of time and get a better idea of what she likes? Remember, this is a ring that she’ll wear every single day and should absolutely love.

Although you don’t have to tell her how much you’re planning to spend or if you’ll absolutely be getting a specific ring, at least you’ll have her input, which will make it easier to make this big purchase when the time comes. Trust me; she’ll definitely appreciate the opportunity to clue you in on what she has in mind. And just imagine the look on her face when you propose with her dream engagement ring….

6 Ways to Secretly Find Her Engagement Ring Size

Alright men, so you’ve finally decided the time is right to pop the question. You’ve picked out the engagement ring, you have the perfect proposal planned out, but one thing is standing in your way: You don’t know her ring size.

Don’t fret because we are here with a list of tips to help you secretly find your future fiancé’s engagement ring size to complete the perfect surprise proposal.

  1. Quiz the Inner Circle

If your girlfriend has a tight knit circle of friends, then one of them may know her ring size. You could also question her mother or sister about her ring size. If they don’t know it, you could ask them to covertly find out and get back to you with the answer. A friend asking about a ring size is less likely to make her suspicious than if you casually ask what her ring size is.

Have someone take her “window shopping” for a ring. Get her to see what her ring size is for “fun”.

However, keep in mind that asking the friends and family members of your girlfriend does take a leap of faith. Whoever you ask must be sworn to secrecy to prevent ruining the surprise. In addition, be prepared to act quickly once you ask someone else to help you. The more people who know what you’re doing, the harder it is to keep it a secret.

friends looking at rings at a jewelry store

  1. “Borrow a Ring”

If you can get your hands on a ring that your girlfriend wears you can take it to a jewelers and get it measured.

However, in order to get an accurate measurement you’ll need to be sure that the ring actually fits her properly and it is worn on the correct finger (left ring finger), as all fingers are different sizes.

If she does not wear a ring on that finger you can settle for an estimated measurement for another finger, but beware the ring will most likely need to be re-sized.

  1. When the Ring Can’t Leave Home

Let’s say you are unable to take her ring to a jeweler without her noticing it’s missing. There are several ways you can estimate the size without taking the ring out of the home.

For one, you can try the ring on yourself and mark on your finger where it falls. Then you can go to a jeweler and have them find the size that falls in the same place.

Also, you can make an impression of her ring in a bar of soap or clay and take it in for measurement.

One last way is to trace the inside of her ring with a pencil and have a jeweler match the size.

  1. Sleeping Beauty

If your girlfriend can sleep through a hurricane then this may be the best method for you to find out what size diamond ring to buy. While your girlfriend blissfully slumbers, unaware of what you have planned you can wrap a piece of paper or string around her ring finger and mark the size that way. However, expect to have a pounding heart and sweating brow as you pray she won’t wake up while you’re tying the string. On that note, be prepared to have an answer as to what you’re doing in case she does wake up.

If you bring this in to a jeweler they can help you to find a measurement. Just make sure she’s not a light sleeper.

  1. When in Doubt: Size up!

A ring is easier to re-size if it is too big, and most jewelers offer free resizing. Just note that thin bands or those which are intricately covered in gems might not be able to be re-sized.

Make sure you check with your jeweler if the ring is re-sizable. Also, if you’re guessing her ring size it’s important to know that rings which have a thick band will need to be larger than her normal rings.

  1. Tell Her It’s For Someone Else

You may be able to get her to divulge her ring size by telling her you want to buy a ring for your sister or mother.

Tell her you want to get an estimated size for someone else and either ask her to try on a ring or ask her outright what her size is.

Beware though; this method could be a dead giveaway if not done right.


boyfriend putting the engagement ring on fiance

Using these tips you should be able to get a fairly accurate measurement of her engagement ring size and be well on the way to spending the rest of your life with the woman of your dreams.

Just remember to keep in mind these important points:

1) You need to find the size of her left ring finger. Rings worn on any other finger aren’t likely to give an accurate measurement.

2) When in doubt size up because it’s easier to resize down.

3) Make sure the engagement ring is resizable.

Do You Need Engagement Ring Insurance?

Congrats — now that you’ve finally found the ring that perfectly shows how much you love your bride-to-be (or as much as three-month’s salary will tell her), don’t forget that final, but very important, step in the ring-buying process: insurance.

There are several ways to handle this. There are a variety of different companies that specifically sell insurance for jewelry. To find one, try a simple search online, or simply ask the store where you purchased the ring. A lot of times wherever you’re buy the ring (especially if it’s a retail store) will have deals, or if nothing else, a recommendation of a reputable insurer.

Ring insurance should run between $50 to $150 per year, depending on the value of the ring.

It’s very important to have some sort of insurance for the ring up front, but once the wedding day is over, consider looking at other options such as adding it to your homeowner’s or renter’s insurance policy. You may find that going that route can be a better deal.

Just remember to keep the appraisal in a safe place so you don’t have to get the ring it appraised again if you switch insurance companies. You’ve spent a lot of time finding her the perfect ring, take 10 minutes and make sure you have a good insurance policy for it in case something happens.

TMR Recommendation: This is an incredibly busy time in your life. Do yourself a favor and go with an insurance company that the jewelry store recommends. The store may even be able to set it all up right then and there. This way, it’s done and taken care of and you won’t need to worry about it again for at least a year.

Should You Ask Her Father’s Permission to Propose?

It’s something that every traditionalist will tell you is a requirement for the engagement — asking the bride’s parents for permission for their daughter’s hand in marriage. Many will tell you that it’s not necessary in today’s modern world — but trust us: They’re expecting it. And if overlook this step, it could be a rocky and uncomfortable start to your marriage.

asking fiancee to be's father for permission to marry his daughter in kitchen

Sure, it’ll be uncomfortable and maybe a little awkward at first. It will probably be pretty obvious what you’re getting ready to ask. Parents can be intimidating, especially if you don’t have a close relationship with them yet.

Fathers and mothers have a special relationship with their daughter and it’s not easy to let go of seeing her as their “little girl.” But if you can muster the courage to spit out the words, we guarantee you’ll feel incredible afterward, not to mention the major brownie points you’ll likely earn from your bride-to-be later for doing the right thing.

Tips for making it all go smoothly:

  • Be sure to tell them how much you love their daughter and how you believe that marriage is a sacred one-time bond.
  • Re-assure them that you’ll treat her with all of the respect that she deserves.
  • We know that tradition mainly mentions asking the father for permission, but it’s a very nice gesture to include the mother as well. She loves her daughter, too!
  • Meet in person. This is NOT something you want to do over the phone. If you live in a different state, get creative and use a webcam (we know you’ve got one, you stud).
  • You don’t want to meet with them at their home or at a coffee shop (boooring). Take them out to lunch or dinner at a favorite restaurant, to a ballgame or an art exhibit —basically whatever will help put them in a good mood and show them how considerate you are.
  • Wherever you plan on meeting with them or taking them out, be on time, and under no circumstances cancel or reschedule! This doesn’t exactly make you look very dependable or reliable as a future husband.

TMR Recommendation: If you’re wavering on asking for permission, think about this: Do you want your daughter’s future husband to bypass you and go straight for your daughter? Show your future in-laws some respect by asking permission to marry their daughter. Remember, future grooms, it pays to stay classy!

Should You Propose in Front of Her Family & Friends?

Should you propose in front of her family and friends? We don’t have a direct answer, but keep reading and it’ll make sense.

Boy Meets Girl

Boy dates girl. Boy falls in love with girl…and wants to spend the rest of his life with her. He saves up, does research, and buys the perfect engagement ring. Things are going great, but there’s just one VERY important detail that needs to be planned—the proposal!

Even if you know what you’re going to say, don’t underestimate the where, when, and how. Any girl will tell you that proposals are a big deal (asking someone to marry you and be your wife is no small feat)!

Just take a look at all of the “proposal fail” videos on YouTube. Asking in the wrong environment or at the wrong time can be downright deadly, embarrassing, or just plain awkward for your future bride.

Is It Even A Good Idea?

Is it appropriate to propose in front of her family/friends? Better yet, is it a good idea?  We got that very question from one concerned groom-to-be. Marty W. asked:

“Should I propose in front of her family/friends? And should I let them know I’m planning on asking? (I’m pretty sure she’s going to say yes, btw, so no worries!) I was thinking it would be nice if they all came out afterwards and we could go out and have a celebratory dinner. Advice?”

young man on one knee and giving engagement ring while making marriage proposal to his girlfriend outdoors.

Keeping Them Away

One former groom (now a married man) Dan L. recommended making the proposal mostly private—no family or friends—since it’s a lot of added pressure. Except for maybe a photographer “covertly hidden taking a photo or video of when you get down on one knee”, but you really shouldn’t need anyone else there except you and her.

The photo/videos are just a mere suggestion to please her oh-so-curious and excited family. Trust us. When she calls them, they’ll want details of absolutely everything—the proposal, the ring, what she said, if she cried, what you said, etc.

Just make sure your bride-to-be is the type who loves documenting all of her important life events. You definitely won’t want to use this idea if she’ll find it creepy!

Proposal? Check! Now On To Groomsmen Gifts

Keeping Them Nearby

Looking for the perfect balance of a personal proposal (but still want to keep her family in the loop?), take a smart tip from one of our experts, Julie Pryor, who had the perfect solution to this question-popping conundrum.

When it comes to proposals, Julie suggested a personal proposal (“just the two of you”). This allows for a celebration with her family for later in the evening or the next day. This is a great way to have her family feel like they were part of their daughter AND future-son-in-law’s intimate moment, without actually having them there!

If you feel like her family would still like to be involved, consider having them hide and wait somewhere (a restaurant, another location, etc). Then when you and your newly engaged fiancée come in, all of you can celebrate together!

It Depends!

In the end, though, we agreed with Roxanna, a user who stressed that it really depends on the girl. She brought up some great points:

“Think about it carefully– does she like to celebrate her birthday with all of her family? Is she really close to them? Are they the first to hear about all of the big news in her life? Even if those things are true, she might not want the proposal to be in front of family and friends.”

She also mentioned that ideally, the couple should be very close to both families if he’s planning on proposing in front of so many people.

engagement ring still in the box

The Bottom Line

“That’s a lot of pressure, and no matter how sure you are that she’ll say yes, she might want to keep the moment private and special with just you. Think carefully in terms of your relationship and if she would like that type of thing– if you have any doubts, I would shy away from it,”

said one smart user, and we agree!

How to Pop the Question

Men: if you’re reading this, you’re most likely ready to make one of the biggest decisions of your life. And because you’re taking the time to research, it means you want to make it as special and original as possible.

Just to reiterate, how you pop the question can really set the tone for the engagement and the marriage. We know it can be a nerve-wracking experience planning it all. Trust us — we’ve been there. The key is to remember to always stay calm and confident.

Now, we won’t tell you exactly how to propose. That wouldn’t really be in keeping with our originality theme. However, here’s some helpful advice that will help slow your heart rate.

Add Some Bling

We understand that times are tough and that rings are expensive. However, if it all possible, have some sort of ring with you when you pop the big question. Even if it’s just a temporary cheapie, a loner or a family heirloom ring — have something!

Make It Original

There’s nothing wrong with asking her to be your wife over a simple dinner. But why stop there? You’re asking her to be your wife — show her why she should spend the rest of her life with you. (Surely, she already knows why, but going the extra mile may earn you a get-out-of-jail-free card the next time your poker night runs late.)

Try to incorporate aspects of your relationship into the event. Something as simple as taking her to the location of your first date is sure to impress her much more than a simple date to Red Lobster (apologies to those who had their first date at Red Lobster — great choice by the way and great crab legs!). There’s also no reason to keep things just to an evening. Try planning a day’s worth of events culminating with your proposal.

Some activities for your engagement day might include: setting up a spa day for her (think manicure/pedicure or massage), going to a sporting event, taking her shopping for a dress to wear that evening, going on a hot air balloon ride, taking a picnic or going on a hiking trip. Remember, include activities that are special to her or your relationship.

Get Down on One Knee

Why do we get down on one knee? Nobody knows. Just do it! You don’t want to know what the backlash will be if you don’t. So don’t even mess around with the idea.

Get the Family Involved

We know that this day is about you and your girl. But including both families, if possible, is a very nice gesture. If you’re planning something elaborate, they may even be able to help you with part of the plans.

After she has said yes, surprise her with a get-together with her closest friends and family. This is a great way to cap off a very big day.

Still Nervous?

Relax. Go grab a beer and think about this: She wouldn’t have put up with you this long if she didn’t know you were the one. Whatever way you ask her will be perfect. Be confident and remember, You Da Man!

TMR Recommendation: If planning an engagement night party, consider inviting or flying in some of your fiancée-to-be’s closest out-of-town friends. We know she’ll have had a day full of surprises, but imagine if her best friend who lives across the country could be there to help her celebrate the occasion. You’re sure to be looking at some major brownie points, not to mention tears of joy.

Do You Have an Engagement Party?

Considering having an engagement party to celebrate the good news? Engagement parties are a great way to share your recent engagement and proposal story with your friends and family. Whether you’re trying to decide if an engagement party is right for you or if you’re looking for some helpful tips for throwing the event, this cheat sheet will help guide you through the process.

Why Have A Party?

An engagement party is a couple’s first chance to celebrate their decision to get married with their friends and family. Oftentimes, it can also give the bride’s and groom’s families a chance to formally meet each other, if they haven’t already done so.

Who Throws the Engagement Party?

While the bride’s family has traditionally been responsible for hosting the engagement party, it’s common today for the groom’s family, a combination of both families or even the engaged couple to throw the event. It’s also quite common for close friends of the couple to host the party or hold a small get-together.

What Type of Party Is It?

An engagement party doesn’t have to be an all-out bash. It certainly can be a fancy affair, but it’s often a bit more casual gathering of family and close friends. For example, a dinner at a favorite restaurant or bar, a rented suite at a sporting event, a brunch at someone’s home or an afternoon BBQ in the hosts’ backyard. Gifts should be optional, but practical if given.

The most important thing to remember is that the party should reflect the interests and style of the couple.

When Should It Be Held?

Engagement parties are typically held one to three months after the engagement, giving those hosting the party plenty of time to prepare. If you’re planning on a short engagement, it’s best to have the engagement party sooner rather than later. This will ensure that the engagement party doesn’t feel like an early wedding shower.

Who Is Invited?

Immediate family, the bridal party and close friends are typically invited to the engagement party. Invites can also be extended further, but keep in mind that any guests who are invited to the engagement party should also receive a wedding invitation.

TMR Recommendation: Grooms, if you really want to impress your bride-to-be, plan a surprise party the night of your engagement. There’s no reason you can’t throw this party yourself!


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