Something like 30-40% of couples get engaged over the holidays.  So, I figure there are a lot of nervous guys out there right now.
Gentlemen, I’ve got your back.  Here are a few engagement tips and considerations.  I’ve heard hundreds of engagement stories.  Some good, some not so good and I’ve learned a lot from my couples.  And, you know, I was once a girlfriend waiting for a ring, so I’ve got her perspective down cold.

Keep it Simple.

At the root of it, all a girl really wants is for the one she loves to ask that question.  Seriously. I remember waiting for Hubby to propose, and all I really wanted was to hear those words.  That’s it.  We could  have been standing in a mud pit and if those words came out of his mouth – I would have been a happy camper.  The minute those words are spoken, the world shifts.  Don’t gloss over the power of that moment.  Those four words are all you really need.  Make that moment just right and you will have a winning proposal.

Surprise Her.

Knowing your engagement is coming is no fun.  Even if you’ve discussed getting engaged before, find a way to make it a surprise.  Take care to throw her off your trail and keep those who know mum.

Pay attention to the Details.

Once you’ve popped the question and the sparkle is on her finger, she’s going to be showing it off.  If you can arrange it, get her Mom, Sister or Friend to take her for a manicure a day or two before the big moment.  You’ll have to find a way to make it not a big deal so she doesn’t suspect, but post-question she’ll be stoked she has a perfectly manicured hand to hold that ring up with, and she’ll be touched you thought of it.

If you want to take it a step further, keep in mind that no woman pictures this moment with unbrushed teeth, bad hair, or a frumpy outfit on.  Take care to make your plan work for a time when she has maybe put some special effort into the way she looks.   One of our friends arranged for his Mom to take his to-be fiance shopping that day (a normal occurrence for them, so no suspicion) and since the Mom was in on it, she knew she had to get a great outfit for dinner into the lucky girl’s bags.

Public or Private?

Think carefully about your fiance and your own relationships with friends and family.  How does she behave in public?  Is she open with her affection or is that reserved for when you are alone?  If you are planning a public proposal, you want to be sure she will be comfortable with it being on display with others watching.   Especially if you are planning to do it in front of family, who will quickly swoop in with congrats.  If you want more of a quiet and private moment, make sure you arrange for that setting.

It’s bigger than the two of you.

As much as this moment is all about you and her, it quickly becomes about so much more.  You are making a move that will join two families.  If asking for her Father’s blessing (or both parents) is something that would be important to her family, then do it.  Whether you agree with the practice or not, it is a sign of respect and will make your path to becoming a member of her family much smoother.   If you are too scared to do this small task, you aren’t ready to get engaged.  I’ll have more advice about post-engagement moves and thoughts to help you down this road soon.

Make it Memorable.

Like I said before – at the heart, you just need the question and a ring.  But finding a way to make it extra special is part of the fun of this.  Think about places that mean something to you as a couple, or to you or her personally.  Think about events or ways you can add a personal layer to this experience.   A special box to hold the ring, a unique presentation maybe (in your dessert, tied to the dog’s collar, etc).  Should it be something she finds?  Something you hold out to her?  It can be something as easy as ensuring a specific song is playing or that you are drinking a certain wine.

Have a camera on hand.

Of course, it would be totally awesome to have me there to document your moment – I promise to hide in the bushes.   But if you don’t do that, have a camera ready.  Take a few shots after you’ve both calmed down a bit.  The joy on your faces is something you’ll want to capture and remember.   Your cell phone just isn’t going to cut it.

Have a plan for spreading the news.

This will be covered in another post of post-engagement tips, but I think it warrants mention here too.  This is huge news, so take care with how you spread it.  Just like I said before – this is bigger than the two of you.  This news is about your parents, siblings and friends too.  Don’t update your status on facebook before you’ve personally told those who deserve to know first.   Tell your parents first – if you have to, call them (or Skype!).  They deserve to be the first to know.  Then move on to siblings, other close family members and very close friends.  Then put it on facebook.  Keep in mind that with this announcement comes a lot of questions.  If you want to keep it to yourselves for a few hours or even a few days, no one would blame you.  And when the questions come, just say “We haven’t gotten to that yet”.

Good luck Gentlemen!