How To Propose: It’s Time To Create A Memorable Engagement Day

Part 6 of 6 of series on getting engaged.  

Oh, boy here we go!

The heart was pounding.  The ring is taped on the inside of my jeans… right next to my ankle.

We are walking into a bar to watch a Michigan basketball game with a bunch of our friends.

The game has started and everyone loves the game.  Beers are ordered and conversations flow.  The normal stuff: “What have you been up to?”  “How’s life?”  “Why is this Michigan game boring?”  (just kidding, that isn’t said in a Michigan bar).

But this is only a pit stop before the big moment.  Yeah, we still are planning to meet an old buddy from college for drinks.  Actually, it is at our first date location.

She’s never met him.  But it’s only drinks, they are in town for a business conference.  And we can only see them in a tight window.

Time is ticking as slowly as it does when your team is up by six points and the opponent has one final drive to win.

It’s time for us to request an Uber and head on down to Proof and Provision to grab a drink with my buddy, who just so happened was staying at the Georgian Hotel (which is above Proof and Provision).

Traffic was a pain in the ass.  Right as we were about to pull into the hotel/restaurant, traffic became a standstill.

We were already running a bit late, so I told the Uber driver to let us out and we would walk the rest of the way.  Which we did, and Hillary thought I was crazy.

This is when things began to unravel.

I started telling Hillary the whole back-story of my buddy and his family.  Telling her really useless information.  But the nerves really hit once we walked into that building.

We made our way down to the restaurant and found a table right near where we had our first date (I thought it was the table we actually sat at, but the restaurant seemed to have rearranged some tables).

We sat and waited for my buddy.  But what she didn’t know was that he wasn’t coming.  Actually, he wasn’t even in the state.  Yeah, he was still in LA.

I had already communicated with the restaurant to play along with the plot though.  And behind Hillary, I saw both of our families peak from behind a wall.

It was go time.


A huge splash doesn’t always lead to huge love

The bigger the event doesn’t necessarily make the moment more or less special.

Women want a proposal that is meaningful.  Something that shows you understand them and that you have been learning about them throughout the entire relationship.

But the problem with us as guys is that we always try to do this huge impressive proposal in order to woo our boo and make it a day she will never forget.

And in reality, something from the heart is likely going to be more memorable to her than anything too over the top.

But I think the reason we always revert to the big splash engagement is due to us not knowing what to really do.

So, in order for us to cover up not really knowing what our lady would sentimentally value, we revert to something over the top to try and hide that unknown.

Big mistake.

We need to remember that proposing to your girlfriend is a big moment.  This is a time when you are asking someone to spend the rest of her life with you.

The real problem is that we need to actually take a second or two and plan this day.  Think through what she likes, what she doesn’t.  What have we experienced within our relationship.  What do we like to do?

Get all of these answered, plus some other questions and we might actually be able to find something that is meaningful and not necessarily over the top.  And if you are unsure with her actually liking the moment, get over it.  She will love it if the moment has thought, creativity and your special twist on it.  That’s why she is going to spend the rest of her life with you.


The proposal ideas to stay away from… even if it is from the heart

After doing some research, here are a couple of proposal ideas that really won’t touch the heart of your future bride.  Actually, they may lead to her not even being your future bride.  So stay away from these things.

  • Proposing while drunk: Ok, having a cocktail or two to ease the nerves is fine.  But getting sloshed with your buddies (or like you do with your buddies) is not the way to go before popping the question.
  • Popping the question in the car: This may not be a bad option, but be sure there is some sort of significance behind the way you pop the question.  One proposal gone wrong that I read about was that they were picking apples during the day (could be romantic) and then they took their friends home and dropped them off.  Right after dropping them off (while still in their driveway), he popped the question.  No bueno, amigo!
  • Sweats and hung over: This is not the best time to ask the lady the question she has been waiting for her entire life if she isn’t feeling well from the night before and wants to just be in sweats the whole day.  Let her be and push back your plans.  She probably doesn’t want to post the news to her Facebook while still wearing makeup from the night before!
  • After an argument: Don’t do what one brilliant dude did.  As he and his loved one were having an argument. He had already been planning to propose to her sooner than later. But he had the brilliant thought that proposing would be a good option to end this fight.  So, he proposed in order to end the fight.  The lady said yes, but now every time she thinks of the proposal she remembers the argument they were having regarding monthly versus annual payments on the car insurance.  That wasn’t a good time for him to put a ring on it!


Here is to going over the top… meant for inspiration, not necessarily duplication

Alright, I know I said you don’t necessarily have to go over the top, but the below proposals are some of the most viewed on the internet.

I thought it would be fun to take a look at some of these.  But in order for you to read on (and view on), you have to promise me one thing.  Ok?

Promise that you won’t let these upset you in regards to believing that how you are planning to propose doesn’t live up to these.  You also have to promise that you won’t try to replicate these.

Remember the proposal needs to come from your heart.  Make your own YouTube sensation.  Make a YouTube sensation that means something to the two of you and not necessarily to everyone else.

Here are five of my favorites with some commentary from myself (they are in no specific order):

The Strung Out Proposal

I love this one.  The idea of toying with her heart, but knowing that you will be providing her with the question she expects later on is great.  This is a truly great way to have fun with the proposal.  My favorite part comes at about 1:42 on the video while they are at the sushi restaurant.  That is true brilliance my friend.  Bravo!


Getting Celebrity Help

This one is actually one of those where a lot of us would have difficulty accomplishing it.  This exposed a specific skill set of the guy (video production) and also the ability to convince a celebrity to help out.  Now, Twitter can make this a little easier.  But a lot of work went into this one.  It actually was really good and from the heart with all the work and the people he got into the video.  Kudos!


Way Out of My League Ok, this one is way out of my league.  But for those who own a plane, not a bad idea. Very clever in the way that he popped the question.  The only thing is that you have to have the plane flying skills to pull this one off.  Seems to me to be very risky; one of those high-risk high reward types of proposals.  Well done, captain!


The (Overly Used) Flash Mob Some of you may be wondering why I would put this one in there.  The flash mob seems to be taking proposals by storm ever since JT made it popular in Friends With Benefits (great movie by the way).  But this one encompassed the cheesiness that I like.  He danced to the Train song “Marry Me” and then popped the question in Disneyland of all places!  Gotta have dance moves for this one.  But good job breaking it down, my friend!


The 6 Year Plan This was a cool video and a great idea.  And it also took a lot of commitment.  I mean he actually knew he wanted to marry this girl for six years!  And he knew how he wanted to propose the whole time!  This dude can really keep a secret.  Probably don’t show this one to your loved one.  Just keep it between us.


The handy checklist for a great proposal

Remember our promise that we made before watching the above proposals.  Stick to the plan and make your proposal special to the two of you.

Here are some things to answer as you sit down and determine the best way of proposing to your baby girl.  After answering them, you may just be able to, maybe, find that special proposal for you both.  And they don’t have to be answered in any particular order.

  • Does she like to be in front of big crowds?
  • What is her favorite activity?
  • Does she like hiking, running or other outdoor activities?
  • Or is she a foodie?
  • Maybe she is a homebody?
  • Is family really important to her?
  • Does she absolutely, ridiculously (and somewhat over the top) love her doggy or cat?
  • What’s her favorite song?
  • Does she like to be with friends?
  • Where was your first date?
  • What was the first activity you all did together?
  • What’s her favorite spot? Venue, park, restaurant, coffee shop, etc.
  • Do you all have an inside joke? Or jokes?


So, sit down and answer these questions.  Put thought into them and by the end of answering them, you should have a pretty good starting point for figuring out how to propose to your girlfriend.

And if you still are unsure of how to pop the question, continue to write out characteristics of your girlfriend until something hits you.  Because it eventually will.


The finale

Back to our moment.

The joke of our first date was that we had this really awkward hug goodbye after our more than two hours of drinks.  We continue to joke about it till this day, although it isn’t the funniest thing, it is a special moment to us.

So, in a fitting manner I had her rise from her chair while we were sitting at Proof and Provision and we reenacted the awkward hug.  I told her to remember that time we met here for our first date and that awkward hug we had.

From there, I got down on one knee and asked my love to be with me for the rest of our lives.  She started crying and we hugged it out.

And on cue, the family’s emerged to wrap up the surprise.

It was meaningful.  It wasn’t in front of an audience or a choreographed dance.  It meant something special to us.  Every aspect of the night meant something to us.  Time with friends, back to our first date spot, the awkward hug, family and then more friends.

But one thing I never mentioned was that shit happened that day.

Yeah, water wasn’t really flowing at the Reiner house.  Pipes got mixed up when service people were working on the house.  We were already late for the Michigan basketball game and showering had to be done in spurts.  Because that’s all we got with the water.

We showered old school.  Towels to wipe us down… separately.  And then, of course, we had to use a little extra deodorant to get that fresh shower smell!

But yeah, shit happened that day.  And we rolled with it.  Had fun with it.  Dealt with it the same way we would always deal with it.  That’s one thing we will never forget about the day.  Because as much as I knew what was about to happen, she had no clue. So, remember no matter what happens during the day or week leading up to the big moment, roll with it.  Take it in stride and soak it in.  This is a big day that you want to remember for all the good reasons.

And remember that no matter how you decide to propose that as long as it is from the heart, it will be meaningful to your future bride.  Don’t worry about what others will think or anything.  This is a moment for the two of you.

It’s that launching point for the rest of your lives!  Go get that love of your life!