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Proposing Guide

If you’re here, you’re at least considering proposing to her. Take a deep breath, and read on.

The Decision

Make no mistake, proposing is the biggest decision of your life. Sorry, that probably doesn’t help in your current frazzled state. But if you’re trying to figure out if this is the right choice, here are some guidelines to deciding whether she’s the one or not.

How you feel: It’s completely understandable and normal to feel a little scared and/or nervous. No guy has ever bought an engagement ring and then proposed without a slight tremble in the hand. Mixed in with that, though, you should be excited to do this. If all you feel is obligation or that you “should” propose and there’s no giddy excitement over the idea of her beaming and saying “yes,” you need to reevaluate. Take some time for yourself and truly look at your relationship, or talk it out with a trusted buddy, brother, or your father. It’s important to get this right the first time.

How you feel about her: If a good friend were to ask what you love about your girlfriend now, what would you say? It might not be as important what exactly you love about her, but if you start rambling on so much that your buddy starts to snore or a insuppressible smile comes out just talking about her, or you even get a tad emotional thinking all that she means to you, then you’re in the right state of mind. On the flip side, if you start thinking of the ways you love her but then start hovering over those pet peeves or nagging qualities that frustrate you all the time, think about how that will grow over years of marriage.

How she feels about you: If you’ve had conversations about getting married and she has told you repeatedly that she needs more time, you need to respect that. If you push ahead despite those conversations, you could possibly push her away for good because she might think you will never listen to her. However, if you think she’s in the same place as you, then this is one of those times to man up. No one wants to get rejected, and chances are, you won’t either. Unfortunately that’s all the reassurance you’re going to get until she says “yes,” but if you’ve passed the first two criteria above, then that’s all you need to reassure yourself with. Just think about losing her and the regret of not showing her how you truly feel. That’s worth a little uneasiness to get the woman of your dreams for good.

Find a Confidant: Once you’ve decided – or possibly to help you make that decision – your very best friend, or a brother or sister, or your dad can help to ease some of your nervousness. Obviously, this confidant has to be the right person who won’t spill the beans, but having even a one-person support base for the biggest decision of your life can feel like you’ve had a weight lifted off your shoulders. And the added bonus is that who you choose to share this news with is an obvious choice for your best man. Now, all that’s left is asking her. 

Romantic Proposal Ideas

Even if you’ve had conversations with her about getting married, and you’ve even looked at rings together, make sure the proposal is as much of a surprise as possible. The reason: She’s been dreaming of this moment since she first had a crush back in second grade. So you’ve got to make this special. Here’s our list of the best and worst ways to pop the big question.

I Do’s

• College days – If you’re college sweethearts, go to the place on campus that reminds you of those first sparks of young love.
• The view – As long as Mother Nature cooperates, a spot with a great view or beautiful sunset is always a good pick.
• Wined and dined – It may be traditional, but the swanky restaurant has always set the right mood for a reason.
• That special place – If we knew what it was, it wouldn’t be that meaningful to the two of you.
• The blockbuster – If you really want to wow her, spare no expense. Whisk her off to Paris or that great coastal resort she’s always dreamed of.

I Don’ts*

• On the scoreboard at a sporting event – you may think a hotdog and beer is romantic, but unless you have some special connection to the team or the place (a la Fever Pitch), this is a surefire way to tell her you’ll end up on the couch watching sports every Sunday while yelling to her to get you another beer.
• On top of a dessert/in a glass of champagne – This is on our “don’ts” list for sheer practicality: the last thing you want is to be nervous she’s going to swallow or chip a tooth on her new diamond.
• In front of the family – This is a moment for the two of you, not for either sets of your parents or extended family.
• On a billboard – For the same price, you could have taken her on a great mini-vacation that would have made much better memories.
• Christmas gift – Are you trying to tell us (and her) that this is a way out of buying a real Christmas gift?

*A caveat: You obviously know your girlfriend better than us. So if you had seriously considered one of our “I don’ts” as the perfect idea, pass it by a buddy and see what he thinks.