“Romantic” Proposal Ideas That Don’t Suck

Four days. Your girlfriend has been looking forward to four days–and, arguably, maybe a few more–her entire life: 1) her wedding; 2) becoming a mother; 3) an event that already happened with some other dude in high school or college; and 4) the engagement proposal. Let’s focus on #4. The proposal matters. And you know this. In fact, you’re probably over-thinking it, sweating it, getting paranoid.

See also: Buying The Ring – How Much Dough To Blow?

If you’re like most guys, you’re having some version of the following inner-monologue: “Okay, this proposal thing needs to be romantic, but I don’t wanna be some damn cheeseball. Should I do it in public? Yeah. Yeah. That’ll make it memorable. Wait, but then I’ll be the dope on one knee in a restaurant asking her to marry me, and what if she says no? And what about the engagement ring, where should I hide that damn thing? And what are the 49ers going to do with their first-round draft pick? The O-Line could use a little–[etc, etc, mind wandering, interest in subject exhausted].”

Your first move? Go read The Plunge’s Proposal MANual and our article 10 Commandments of Popping the Question. You’ll find plenty of advice on how to think about the marriage proposal, how to scheme, how to not screw it up.

But maybe you need some actual, concrete inspiration. We’ve rounded up the most common, cool proposal ideas (and the uncool) and given you the Pros and Cons. Good luck.

The Family Gathering Proposal

If she likes: Awkward public moments.

Pros: Very few. If her parents already love you, perhaps they’ll love you even more. Also, you won’t have to spend hours serially calling all of her relatives and repeating how-you-proposed stories and announcing your engagement–they’re all there already. Whhooo.

Cons:  This type of proposal can put crushing pressure on her, is awkward for the family, and can rob the moment of all its privacy and dignity. Plus, proposing in front of the family is what the bad guy does in romantic comedies–Bradley Cooper in Wedding Crashers, Cal from Titanic, and the Soul Glo guy from Coming to America. Don’t be the Soul Glo guy.

Airplane Letters in the Sky

If she likes: Attention, aviation

Pros: Can be dramatic. Creates the sense that this is NEWS, something that everyone within a 3-mile radius must know about, and must know about now. Also, if you’re truly daring and want to risk some pinpoint timing, you can combine this with any other proposal idea and use it as the punch line for when you’re ready to ask the question, “Will you marry me?”

Cons: There’s risk. Do you know precisely when this will happen? Are you absolutely convinced you can get her outdoors at the right place at the right time in the right weather…and that the pilot spells the right name?

Found Mrs. Perfect?  We’ll help you find the perfect ring.

The Sporting Event

If she likes: Attention from 16,000 strangers.

Pros: This one’s tricky. Remember that the marriage proposal is about her, not you. So if you’re a die-hard Orioles fan and think it would be badass to propose to her at a game, well, don’t. Only do it if she’s the die-hard Orioles fan, and even then, only do it if she’s obsessed. And don’t do this in a playoff game. That last “playoff game” rule is less about romance and more about male-etiquette. Dude it’s the playoffs. Show some respect for your team.

Cons: If the answer’s not “Yes,” you’ll blow $60,000 on therapy over the next 10 years to get over your humiliation.

Cook Her Dinner

If she likes: Quiet evenings at home more than trendy hotspots

Pros: This works best for guys who never cook. Seriously. It’ll mean that much more to her. Besides, cooking a meal isn’t really that damn hard. You just find a recipe and follow it.

Bonus: sometime in advance, get her to confess her absolute favorite dinner ever—including details on side dishes, appetizers, and dessert. If you’re desperate for information and she’s tight-lipped, resort to the old “What would you order for dinner as your last meal before you’re sent to the Chair?” trick. Recreate this meal faithfully down to every last detail, minus the electrocution.

Cons: You need to dress it up (flowers, a cartoonish amount of candles, you wearing a tie, etc.), otherwise it might be too ho-hum.


If she likes: Mountain Dew, the X-Games, saying the word “bitchin'”

Pros: We suppose this could work for a certain kind of woman, but you need to be abundantly certain that she has thought about getting engaged, is ready for it, expects it any day now, and the marriage proposal itself is just a formality. A sudden surprise or shock could lead to her freaking out and forgetting to open the parachute, which might cause the not-ideal downside of…

Cons: Death.

The Romantic Restaurant

If she likes: Stability, tradition.

Pros: It’s the right setting: flickering candles, white-gloved waiters, soft music. You’ll both feel like celebrities as you soak in the thrill of the spotlight. You already have a venue picked out for your 5-year anniversary dinner, so there’s that.

Cons: While it’s not quite as garish as a hockey game, there is still a public audience. Make sure this is a done-deal.

The Scavenger Hunt

If she likes: Nostalgia, kitschy adventure, Chuck-E-Cheese

Pros: All cynicism aside, it will probably be a lot of fun and she’ll find it pretty damn charming. If you go this route, make sure the “clues” incorporate all sorts of personalized references and inside jokes. This shows you know her, you get her, and that you’re so in love you’ve spent 17 hours plotting this little Easter egg hunt.

Cons: You’re hiding your very expensive diamond  engagement ring. Which could mean losing your very expensive diamond engagement ring. Note: hopefully you should realize this on your own, but hey, we’re not taking any chances: don’t bury your new $X,0000 bauble somewhere then leave it. Maybe bury something else, like a note that says “Will you marry me?” then as she’s reading it you pull the ring out of your pocket and finish the question.

Walk on the Beach

If she likes: Fairytale romance.

Pros: This one’s tried and true. You’re letting nature do the work for you—the lapping of waves against the shore, the warm feel of sand between your toes, the soft glow of twilight.

Cons: Screaming children, crabs, jellyfish, large men in tiny Speedos. Obviously scout your beach in advance and ensure it’s secluded and safe.

The Hike

If she likes: Well…hikes.

Pros: For the woman who’d rather kill an hour at REI than Tiffany’s, you can do a lot worse than a hike to some romantic vista. Do your homework and hunt for the best spots—-waterfalls, mountain peaks, breathtaking views, nature. Pack a picnic that includes champagne and her favorite food. Don’t even think about hiding the ring under a rock, or we’ll come steal it ourselves.

One more advantage of this one: if you play your cards right, you’re miles away from cell phone range and you can postpone those 178 “announcement calls” she has to make.

Cons: You might drop the ring into a waterfall and never see it again. If your destination is too well-known, it might be crawling with tourists, boy scouts, and those weird old-people-hikers who walk with ski-pole-thingies. Think about going somewhere off-trail or less populous.

See also: Inside the Mind of the Bride: Does Size Matter?

Where You First Met

If she likes: You.

Pros: We like this because it’s personalized. Depending on the venue, this will require a little ingenuity on your part. If you met at the park while playing frisbee? Easy money. More complicated, though, if you met at a dance club, prison, or free clinic.

Cons: Obviously this is all dependent on the venue, but what you can do is incorporate the meeting-place into a more elaborate date.

Say you met at a bookstore. You can take her to dinner and a four-star hotel, but as part of the date you casually swing by the old bookstore to do a little browsing. You don’t even need to pop the question there, but incorporating it into the evening will add a personal flourish to your proposal.

The Hot-Air Balloon

If she likes: 3rd-tier “chick flicks” like Maid in Manhattan,  Never Been Kissed, and Sweet Home Alabama.

Pros: It’ll give her something to talk and brag about, even if her friends roll their eyes behind her back. Okay, and we’ll be honest, there’s something undeniably thrilling about floating over the country at sunset, toasting champagne, and making out with your new fiancée.

Cons: What’s the hot-air-balloon-operator dude supposed to do, just sort of awkwardly look to the side like nothing’s happening, pretend he’s chatting on his cell phone, or really get into the act and give you both his blessing on your happy engagement?

The Kiddy Proposal

If she likes: Teaching, babysitting, spilled applesauce

Pros: We see this proposal recommended a lot—it’s like what Ben Stiller tries at the beginning of Meet the Parents. You’ll get huge points from her parents, older siblings and her child-rearing friends that don’t have sex anymore.

Cons: Dude. You just asked a bunch of 7-year-olds to carry your weight. Another downside: when she says yes, you’ll both be standing awkwardly in front of a throng of kiddies, meaning you’ll only get a chaste kiss, maximum.

The Plunge Endorsement: the Vacation

If she likes: Things that don’t suck.

Pros: You get away from your routine. You suddenly open up a million possibilities for outside-the-box activities: horseback riding, scuba diving, whatever. You can throw in a nice hotel. And most importantly, you get a much-needed smokescreen. She won’t necessarily realize that your romantic activities are prelude to a marriage proposal, she’ll just think they’re part of the vacation.

Cons: It ain’t cheap. And if she says no? That’s one long, loooong-ass plane ride home.

After Pulling it Off: Executed an Awesome Proposal? Exploit It Here

Obviously, this list is nowhere near comprehensive. It’s a starter list, the basics. If you have your own proposal story you want to share, either post it in the comments or drop us a line.

Looking for the right engagement ring? We’ve got you covered.

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