“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) the engagement proposal; 2) becoming a mother; 3) an event that already happened with some other dude in high school or college; and 4) her wedding . Let’s focus on #1. The proposal matters. And you know this. In fact, you’re probably over-thinking it, sweating it, getting paranoid.

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 mope on one knee in a restaurant asking her to marry me, and what if she says no? And what about the engagement ring, should I hide the son of a bitch? 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].»

We’ve rounded up the most common, cool proposal ideas (and the uncool) and given you the Pros and Cons.

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. And you won’t have to spend two hours serially calling all of her relatives and repeating how-you-proposed stories and announcing your engagement—they’re all there. Whhooo.
Cons: Don’t do this. Ever. It puts crushing pressure on her, it’s awkward for the family, and it robs 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 that guy.

Airplane Letters in the Sky
If she likes: Attention, avionics
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?

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. And frankly, cooking a meal isn’t really that damn hard. You just find a recipe and follow the bastard. 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 in case you get electrocuted?» trick. Recreate this meal faithfully down to every last detail, minus electrocution.
Cons: You need to dress it up (flowers, a cartoonish amount of candles, wear a tie, etc.) otherwise it might be too ho-hum.

Sky-Diving

If she likes: Mountain Dew, the X-Games, saying the word «bitchin'»
Pros: We suppose this could work for the 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, all that crap. 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, still, there’s public pressure. Make sure this is a done-deal.

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, and jellyfish. 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 vista. Do your homework and hunt for the best spots-waterfalls, mountain peaks, breathtaking views, nature-shit like that. 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. (More tips on how to announce the engagement here.)
Cons: 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.

Where You First Met
If she likes: You.
Pros:
We like this because it’s personalized. Depending on the venue, this’ll require a little ingenuity on your part. If you met at the park 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. For instance, 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 Still tries at the beginning of Meet the Parents, where you somehow involve a gang of toddlers in the proposal. You’ll get huge points from her parents, older siblings and her 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 of outside-the-box activities: horseback riding, scuba diving, whatever. You can throw in a nice hotel. And most importantly, you get some 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.

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