Wedding Proposal Tips and Ideas. - How to Propose to Your Girlfriend

How To Propose To Your Girlfriend

You know, back in 5th grade all this seemed sooo much easier. You just threw some gum in her hair…or made fun of her glasses… or put a live frog from the science room into her backpack. And voila! Just like that, you had brilliantly and eloquently professed your undying love to your secret crush. Now, however, “what to say” and “how to say it” have never been so daunting. You may have known you wanted to spend the rest of your life with this girl since you first laid eyes on her… but asking her to spend the rest of her life with you has got you absolutely terrified. First of all, breathe. If you’ve been together long enough to know she loves you, and you definitely love her (hence all the nerves and longing for the days of science class frogs), the rest just requires some thinking, a plan, and, oh yeah…a ring. 

Figure out your budget – Yes, you love her. You’d love to give her a rock so big and shiny she could ice skate on it. But let’s be real. You have a definite budget. While there’s no “right amount” to spend on an engagement ring, the good news is that you can purchase a ring on a payment plan (not a credit card) these days, which lets you get a little more bang out of your buck. If you do plan on paying in full though, you will need to determine how long you will need to gather the necessary funds, then plan the proposal date around that.

Find the ring – First, you need to know a little something about your girlfriend’s taste in jewelry (please tell us you pay attention at least a little bit?) If you’re drawing a blank, take a look at what she wears every day, or what she wears when she goes out. Every day jewelry is a good indicator of her preference of style. If she doesn’t wear much every day jewelry, “going out” jewelry will give you the “maximum-bling factor” (do not pick out a ring that has more bling than what she opts for when she’s really dressed up).

Once you have a handle on the style she’d like, it’s time to get down to specifics. If you’ve heard of “the 4 C’s of diamond rings” before, you’re ahead of the game (even if you think the C’s stand for “confused,” “clueless,” “crazed,” and “crying when you see the price”). They actually stand for cut, clarity, carat, and color of the diamond. Your budget will determine most of these, but there are a few tips to keep in mind:

  • Picking out a diamond and a setting separately will help you have more control over what you’re spending your money on. For instance, platinum is nice, but it’s also the most expensive. Why pay extra there, when 14 KT white gold will be just as comparable in terms of looks and quality?
  • For the most part, the “clarity” will determine the price of the diamond. Here, you can consider a diamond with slight inclusions (inclusions = “flaws”). Honestly, most inclusions can only be seen with a magnification of 10x, so unless your girlfriend is one of those “I’m going to get this under a magnifying glass ASAP” types, you should be okay choosing a diamond slightly lower on the clarity scale (which will translate into slightly more on the carat size, which, in turn, might make your girlfriend happy).
  • Consider a reputable online retailer. Yes, a bricks-and-mortar retailer is great, since it allows you to actually go and see the ring/diamond/setting in person. But the online retailer doesn’t have that overhead, so you may be able to find a better deal.

If, on the other hand, you and your girl have already discussed rings, or gone ring shopping…well…1) you’re lucky to not have the pressure of picking a “forever” ring resting solely on your shoulders, and 2) you just wasted 2 minutes of your life reading this section (which makes all the guys who do have the pressure of picking a “forever” ring resting solely on their shoulders a just a wee bit happier).

Find out her ring size – Here begins your subterfuge (if it makes you feel better, you can don a well-tailored suit, pour a dry martini, shaken not stirred, and play the James Bond theme on a loop). Sure, you can buy the ring and worry about sizing it after the question is popped, but, to score extra “my guy is the most amazing guy ever” points, have the ring perfectly sized beforehand. You can take one of her rings to a jeweler and they can size it. But, she might notice it missing, so you can request a sizer from a jeweler and have them send it so you can size one of her rings yourself. Or you can also consider asking her BFF or mom if they know her ring size…but then that will bring more people into the plot too soon, which might not be great for this whole “subterfuge” thing.

Buy the ring (and keep it secret) – Part 2 of the subterfuge. If you don’t share accounts with your girlfriend, then you don’t have many worries here. She’ll be none-the-wiser to a withdrawal of a few thousand bucks. However, if you do share accounts, this might get tricky. Once you’ve made the decision to take the plunge, you can set up a separate checking/savings “ring” account without her name on it, that way there will be no paper trail. If you buy the ring on a credit card and you’re living together, make sure she doesn’t open your mail. If she does open your mail…don’t buy the ring on a credit card (duh). And once you have the ring, make sure to hide it in a safe, girlfriend-proof area. Safety deposit box? Your parents’ house? Buried in the back yard? The possibilities are endless…just don’t make the hiding place so good that even you will forget where it is in a few months.

Ask permission – This is where the subterfuge gets tricky. Yes, the more people who know, the greater the chance she will find out before this particular stew has come to full boil, but, if your girlfriend’s father means a great deal to her, you know what needs to be done. On the plus side, most dads will keep the secret, as long as you plan to propose within a reasonable amount of time. You tell them you plan to propose in two years, well, there might just be an expiration date on their silence. Your situation is a bit trickier if your girlfriend no longer has her father, or if the relationship is strained. Good news is that these days, it’s acceptable to ask one, either, or both parents. And if none of these are options, you could consider asking another close relative.

Pick your words – If you’re the “winging it” kind of guy, more power to you. But, by in large, this is not really the best time to “wing it.” She’s going to remember this moment forever. She’s going to relive it. She’s going to tell her friends and family. Given all that, you might wanna jot some words down. It’s not a test, so relax. You love tell her that. Tell her why you love her. Tell her why you want to spend the rest of your life with her. And then, ask her to marry you. It’s not a proposal without those words, so say them.

Pick a spot – There are so many possible options here, it might be a little overwhelming. But again, just relax, and think about each:

  • A place that’s meaningful to her, or to both of you. It could be where you met, where you went on your first date, or her favorite place to go and spend time.
  • A quiet evening at home, candles, with a special dinner cooked by you.
  • In front of family and/or friends
  • Romantic restaurant…but be sure to do it early in the meal, before you both get stuffed to Willy Wonka/Violet Beauregarde proportions and can only thinking about going home and lying down until sometime next week.
  • Walk along the beach…just be sure not to drop it into the sea/sand/a rock crevasse filled with seaweed and eels.
  • Hot-air balloon ride…again…DO NOT DROP IT.
  • A romantic weekend away. A proposal would knock this little getaway out of the park, but unless the getaway was already planned, involving it into the proposal does add a lot to the budget.


  • Propose on a Jumbotron at a sports event
  • Tie the ring to an animal
  • Drop the ring into food/drink (hello…choking hazard?)
  • Involve the proposal with a prank in any way, shape, or form (even if Practical Jokers is her favorite show)

Kneel down, you fool! – Okay. It all comes down to this. This question. This moment. No pressure at all then, right? Seriously though… she is the love of your life… the ONE. You have the ring, you’re at the perfect spot, you know what you’re going to say (more or less)… so, when the moment comes…do it right. Get down on one knee, look up into her eyes, take her hand (or hold the ring), and ask her to marry you. (Trust us, you will be able to live off the “most amazing and romantic guy in the history of amazing and romantic guys” points you earn here for months!)

One proposal down, congratulations! Now it's time to propose to the groomsmen. The best way to do this is with groomsmen proposal gifts and custom groomsmen gifts for when the big day is close.

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