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The Guys’ Guy’s Guide to Getting Married – Part 2 (The Engagement)


I like to keep things simple and try things once. That includes getting engaged, being married, and having a kid.

Been there done that. I’ve read a lot about putting a ring on it, most of it from the female perspective. Women have invested lots of psychic energy into the details and finer points of popping the question and the wedding. And they should be applauded for all the articles and posts, and also for putting up with their guys throughout all the ceremonial hoopla. The actual process of getting engaged is the trickiest aspect to getting married because in most cases it’s the guy who is doing the asking. With that in mind, a few young bucks have asked me to write about managing this process, so I wanted to share my Guys’ Guy’s point of view about this important milestone.

Let’s begin by clearing stating that there is no set blueprint to getting engaged. There are a lot of ways to do it right and just as many to screw it up. You can post your intentions on the scoreboard of Yankee Stadium or get down on one knee on the beach at sunset. It doesn’t matter where or how you do it, as long as it feels romantic and holds meaning for both of you. Ultimately it’s about following your heart, and then using your mind to make getting engaged a memorable event. Here are a few considerations for each of the critical steps.

1. Make sure she’s the one – There has never been a truer old adage than “fools rush in”. How many friends do you know who got married too soon to the wrong person only to find themselves in a divorce a few years later? There is always at least one broken heart and often kids involved. So what’s the hurry, people? I don’t believe in starter marriages. Instead I say wait. Wait and wait until you are sure you have found the right person to share your life with. You’ll need check marks for companionship, kindness, values, sex, and a shared sense of humor for when you’re both faced with life’s random occurrences. Then to be sure, double and triple check your heart again. If everything feels right, then go ahead, amigo, and make your move.

2. Buy a ring – If you have step one in order and you know that she is ready to commit to spending her life with you, then I suggest buying ring before asking for her hand in marriage. Some people still follow the tradition of asking her father ahead of time. If that works for you, then do it. But first ask yourself what you are going to do if he gives you the thumbs down. Hmmm. That’s tricky. In any case sniff around to see if you can sort out what type of rings she prefers. I’m not sure it’s wise to ask her friends or sisters because they might blab. But whatever you determine to be the right fit for her and your spending limit, add another twenty-five percent to your budget. You never want t take the chance of looking like a cheapskate for the rest of your life because you wanted to save some coin on the ring. Another tip is asking your married friends where they bought their rings. If you’re lucky, you might score a contact in your local Diamond District that could save you a few grand on your purchase.

3. Pop the question- She’s the one, check. Got the ring, check. Now it’s time to ask her for her hand. There are endless ways to do this, but make sure it feels romantic and special to the both of you. This way you’ll always share a great memory of when you got engaged. I asked my future wife out to dinner on a sultry summer night. We headed to an old school, cash only Italian joint in Brooklyn Heights. After our pasta and red wine, we took a walk along the Brooklyn Promenade. When we stopped to enjoy the lights of Manhattan I reached for the ring and dropped to one knee and proposed. I told her that I loved her and that she was the one for me, or something like that. Then I said, “How about it?” She laughed and said, “yes”. Okay, it wasn’t perfect, but we both have a funny memory of that wonderful evening. And she still loves her engagement and her wedding ring. We picked out the wedding band the following week.

Now, I’m not suggesting that this is the way to do it, but it worked for us. There was great food and wine, a starry summer’s night and then me on my knees. So use your noggin’, come up with a plan, buy the ring, and be ready to look into her eyes and pop the question

4. Set a date and stick to it- How many young couples do you know who say they are engaged, but never seem to lock down a date to actually get married? My advice is to do your very best to find a date within a year of your engagement. If necessary, add a few months. But that’s it. If you guys really want to get married, you’ll make locking down that big date a priority. If your timeline keeps getting pushed back and back and back, it’s not a great sign.

5. Keep it fun- After dealing with all the pressure of deciding on the right person, picking out the perfect ring, coming up with a memorable way to pop the question, and then finding a date and all of the other wedding details, it’s important to remind yourselves that the reason you are going through all of this is because you love this person more than anything and you want to have a happy, fun life together. Don’t ever forget the fun factor. If you are finding that the process is more a chore than a pleasure, remind yourself to keep it light. If the whole thing becomes a total drag, then buyer beware. Because you ain’t seen nothing yet, and by that I mean the final step in the process— the wedding.

Until next week…