Wedding Engagement Guide for Men

By no means do I believe I’m the standard when it comes to planning or organizing an engagement. But the one thing I’ve learned over 31 years of manhood is that men don’t care for expert advice, they are more interested in the common man’s word. If this assumption is accurate then you’ve come to the right place. And much like everything else in life that requires planning and structure, unless the ask is locating a bar to get shitfaced at, my fellow bros don’t know what the fuck they are doing. Though to be fair, when it came to going down the path of engagement I didn’t know what I was doing either. The 4 C’s? Ring insurance? Expressing my feelings in an outward fashion? It was all Greek to me.


This was the most important factor to me mainly because I knew it would be the most important factor to her. As some of you may already know, my wife is a bit fashion forward and has rather expensive taste. I’m not going to go into the details of some of her head scratching fashion purchases mostly because it’s unlikely she will cook any meals for me in the next four to six weeks if I do.

If you’re trying to do something special for the ring, I think it’s wise to start the process at least a couple months before you plan to propose. I knew I wanted a custom ring, so I needed to leave plenty of time to get this perfect.  If you do this half-assed that’s kind of what you’re building the basis of your engagement and eventually your marriage on. Keep in mind she’s going to be wearing that bad boy all day, every day until she wants to upgrade in twenty years at which point I doubt I’ll be writing blogs and you’re on your own. This is your best friend you’re shopping for; you need to KNOW she’ll love it.

I don’t want to scare you and say jewelers are on the same level as used car dealers but there are definitely people out there that will try to take advantage of you. So do your research and shop around. Unless you’re on a budget steer clear of the big chains like Jared, Zales, and Kay. While everyone loves a smoking hot plate of fajitas, I imagine you wouldn’t take your girl to Chili’s for Valentine’s Day, so why would you buy her ring at the jewelry equivalent?  Find a private jeweler. Many major cities have jewelry districts you can go browse around. My jeweler was in a strip mall in Suburban Chicago. A quick Google search should yield plenty of results for reputable jewelers. Leverage Blue Nile to get started. This should give you a chance to map out what you’re looking for and get an idea of what it’s going to cost.

Keep in mind high end jewelers like a Tiffany’s or Harry Winston are great, but they are the designer brands of jewelry. If having a designer ring is important to her then by all means there is absolutely nothing wrong with that and you’re going to get a great piece. But keep in mind, just like designer anything you will likely end up paying hundreds/thousands of dollars more getting a name brand piece at places with a brand name attached to it. If you’d like to get more bang for your buck without sacrificing quality, find yourself a private jeweler.  If she has never insinuated the desire to have an engagement ring from David Yurman your dollar will go a lot further somewhere else.

My biggest advice to guys trying to pick out the perfect ring is to take note of everything your girlfriend says about what she wants in said ring.  Anytime Jenna mentioned anything about a ring: cut, shape, design, etc. I took a note of it. One comment here, an observation there, after nearly a year and a half of note taking you will thank yourself immensely. I started a note in my iPhone titled “Baseball” knowing that in the event she browsed through my phone she wouldn’t even consider looking through it.  Similar to a side chick’s name in your phone titled “Pizza Hut” (not me of course but I’ve heard stories!). After all, your biggest fear should be that you get to the point where it’s time to shop for a ring and you have no fucking clue what you want.

I sat down with my jeweler and told him A) what cut of diamond I wanted, B) the desired carat size, C) passed over the notes I had compiled regarding the ring setting, and D) the amount of money I wanted to spend.

With the criteria I’ve described, can this be done for X amount of dollars?

If yes, from that point on it’s pretty much in their hands to create your vision. That’s what you’re paying them for after all, their skill and experience of painting the picture you have described for them. Like anything else there may be minor obstacles that arise, a tweak here and an adjustment there but you’ve done your part.  Workout a timetable with the jeweler on when you can expect the finished result.

One last pro tip I’d like to share: since I bought my ring at a jeweler outside the state of my residence (earmuffs IRS) I was not charged sales tax. If you can look past this logistical hurdle, I’d say it’s worth the extra hundreds/thousands of dollars you’ll save.


Oh you thought once you had the ring you were finished? Not quite. You sacrificed too many bar tabs and weekend trips with the boys for you to misplace the ring or drop it down a sewer drain. I would recommend insuring it as soon as you have it in your possession as insurance covers whether it’s lost, stolen, or damaged.

The price of your insurance premium will be weighed on a number of factors, including your zip code (likelihood of getting mugged), if you own a safe (i.e. you’re a drug kingpin), and the amount of your deductible. A good rule of thumb is the annual premium to cover the ring is approx $1-2 for every $100 it’s worth. So if you have a $15,000 ring, you should expect to pay about $150 per year. Much like your car insurance where you live will play a major factor in the premium cost. In my case when I moved from Los Angeles to Chicago the premium decreased about 50% which was quite drastic. Obviously the main factor is what the ring is worth which is why you should have the ring appraised by a certified gemologist so you have the true value of your ring. Note that the appraisal will likely come back showing it’s worth more than what you paid.

Now that I’ve convinced you why you need insurance and what factors it entails, let’s review the options to get it insured. My recommended method and most cost effective option would be adding a Personal Articles Policy (name may vary) to your existing renters or home owners insurance through your provider, i.e. State Farm, Allstate, Geico. Sorry but just having car insurance won’t cut it. If nothing else, you can use this as a good excuse to get renters insurance which is pretty inexpensive (national average is $144 per year). Simply contact your insurance agent and let them know you have some jewelry you want insured.

If that route isn’t an option, there are several online based insurance providers whose sole focus is jewelry insurance. The two most prominent are Jewelers Mutual and Lavalier. I started out insuring Jenna’s ring through Jewelers Mutual and the process was seamless. I had to fill out an online questionnaire around the factors aforementioned and uploaded a copy of the ring appraisal and boom it was covered. While Jewelers Mutual was quick and easy, the cost was exponentially higher than having it covered through my regular insurance (which I learned later on). Seeing as you likely just blew your life savings on a piece of metal the size of a Life Saver, I would assume you’re not in the market to throw down a ton of bank on an insurance premium you didn’t know you needed five minutes ago. Therefore, my recommendation is going through your insurance provider to protect the ring.

The Proposal

For some guys this might be the easiest part and for others it may be the hardest. There’s countless routes you could take to pop the question, for example a candlelight dinner, high atop a ski slope in Vail, or murdering her ex-boyfriend and using his blood to write “will you marry me?” on the walls of her apartment.

The best vision when planning how to ask the gal in your life to marry you is to think back to when you broke your arm in high school. You had to tell the same story over and over as each person that noticed your cast wanted the details of how it happened. Did you knock a dude out with your fist or did you get pushed off your Huffy bicycle like a weenie? The same will occur when people see her ring. Unless you’re a selfish douche-bag I imagine you would like for it to be a story you’re both proud of and this is your opportunity to write the script. While the ring acts as a symbol, the story of how you got engaged is a reflection of your affection and thoughtfulness.

I’ve heard plenty of uninspired stories of how couples got engaged, and I’ve heard some that set the bar pretty high. If you’re not creative by nature there’s plenty of YouTube videos to give you inspiration. But to simplify things, ask yourself what’s she passionate about and find a way to incorporate it. If she’s an avid Yogi, coordinate with her Yoga studio to surprise her in class. If she loves travel, get down on one knee underneath the Eiffel Tower in Paris (no the Eiffel Tower in Vegas will not suffice). If she’s close knit with her family or friends, find a way to integrate them or have them present for the moment. Ultimately you don’t want to come off as lazy and bland but the expectation isn’t to have mini-Pomeranian’s falling from the sky. Plan properly, keep it simple, and make it meaningful. If the plan is too elaborate, anything that can go wrong likely will.

When it comes time to ask the question you should be prepared for your brain to turn to mush so keep your comments short and to the point. Luckily for you I have created the PFF method (patent pending): One sentence about your past (we’ve been through so much these past three years….), one sentence about your feelings (you’ve made me feel like….), and one sentence about your future (I can’t wait to spend the rest of my life with you…) Three sentences maximum before dropping the ole “will you marry me?” You’re going to be so nervous you’ll likely be stumbling and/or forget your words, and once you open that ring box you will have lost her attention.

Congrats, you’re now engaged and have signed up for sex with only one women the rest of your life, which is like having one song on your iPhone. I hope you chose wisely!


That concludes my Ted Talk. If you’re feeling overwhelmed, I’ve created a 9-step checklist to help guide you through this process.

  1. Compile Ring Criteria
  2. Find Jeweler That Is More Credible than the Dudes that planned Fyre Festival
  3. Purchase Ring
  4. Have Ring Appraised by Certified Gemologist
  5. Purchase Ring Insurance
  6. Plan Proposal
  7. Drink a Bottle of Tequila
  8. Pop The Question
  9. Live Happily Ever After (An average of two weeks i.e. before wedding planning begins)