48 Proposals That Ended Up Being Disasters Instead

Engagement season is upon us. It's that time of year when people get all gooey and decide it's time to commit for life. "Generally, engagement season takes place from Thanksgiving to Valentine's Day, with Christmas proposals being a popular option for many couples," explains wedding planning site, The Knot.

The Knot's 2025 Real Weddings Study found that about 47% of couples get engaged between November and February. The site's experts believe that people pick this time of year because it coincides with the holiday season... a period often spent with family and friends. What better way to celebrate?

Of course, not all proposals go according to plan. And if you want yours to fly instead of flop, experts say planning - and timing - are key. Most importantly, you and your partner should be on the same page to avoid an embarrassing "no" in response to your big question. But also to avoid your marriage ending in divorce in the future...

"It's important to have conversations throughout your pre-engaged relationship about a myriad of topics, from having kids to living together," warns The Knot.

The site's "Jewelry & Engagement Study" found that prior to getting engaged, 51% of couples owned a pet together, 69% of couples lived together, 78% talked about political affiliations, and 87% spoke about the possibility of having children together in the future. But the most important topic was finances. Eighty-nine percent of couples polled said they discussed how to manage their money before getting engaged.

When it came to the issue of whether or not to get married, more than half of couples surveyed said they started talking about a possible engagement more than a year before the actual proposal. Only 2% said they never discussed it at all.

It's a crucial conversation, warns The Knot. "Not only does this reassure you that you're proposing to someone who wants to be married, but it also helps you build a foundation for your future wedding planning experience," explains the site, adding that you should really listen to your partner's thoughts on the topic before going out and buying a ring.

On the subject of rings, a surprising 77% of "proposees" polled said they were involved in selecting or purchasing their engagement ring in some way. Eight-in-ten proposers revealed that their significant other dropped hints about the type of ring they wanted.

"Shopping for the engagement ring together isn't unheard of either, with 29% of couples saying that they intentionally looked at designs together before the proposal," reports The Knot. The site's experts suggest that you ask your partner directly if they want to be involved in shopping for the ring.

If you're pinching pennies, you might be relieved to know that the average cost of engagement rings has gone down over the past few years. But that doesn't mean they come cheap. The Knot's "Jewelry & Engagement Study" found the average cost of an engagement ring is now $5,200. It was $6,000 in 2021.

Experts suggest setting a realistic engagement ring budget before you start shopping so you don't spend what you can't afford. The survey revealed that 71% of proposers had a budget and 92% of proposers paid for the engagement ring on their own.

If some of the horror stories in this listicle have taught us anything, it's that planning is crucial. "Think about what your partner loves and what their dream proposal would be," suggests The Knot. "The key to pulling off an epic proposal is to make it as unique and personal to your partner as possible."

For example, if your SO loves watching movies and spending time outdoors, you could consider setting up a projector screen outside with blankets, pillows, and their favorite foods. Play their favorite movie, then put it on pause or wait 'til the credits roll before popping the question.

Don't wing it, warns The Knot. Figure out long in advance what you're going to say during the proposal. There's the tried-and-tested, traditional route: "Will you marry me?" at the end of a heartwarming speech. Eighty-seven percent of proposers polled said they did this... but you can do or say what you want - as long as it's special.

"No matter what you decide, make sure you speak from the heart and practice your speech before the big day," suggests the site. "By rehearsing ahead of time, you'll feel less nervous during the proposal. But don't feel worried about stumbling over your words—it's an emotional moment full of excitement and jitters, it happens."

While the one doing the proposing has the biggest task, that doesn't mean the other partner shouldn't also prepare. If you've been talking about getting engaged, and you have a feeling it'll happen soon, start thinking about how you'll respond when it does. Experts suggest something more than just "yes." That's provided, of course, that you don't say "no."

"Think of some sentimental things to say to your partner after the big question," notes The Knot's site. "You don't need to have anything memorized or practice a speech ahead of time, but it would be a sweet gesture to say how you feel about your fiancé and how excited you are about your future together."

Don't get caught off-guard with chipped nails or dry hands. Prepare for engagement season and ring photos by doing some double-duty moisturizing, advise the experts. "Slather up your hands every night before bed with your favorite hand lotion (with gloves to lock in the moisture, if you so choose) to make sure they look perfect for those professional photos and Instagram selfies."

Bear in mind that your ring might not fit perfectly the first time. But experts suggest that you don't run to get it resized immediately - unless it seems way too big.

"Your fingers swell in the heat, so if you do decide to size down, it'll be very snug during the hotter months (and you could risk it not fitting at all)," explains The Knot. "And in cold weather, your ring might be looser than normal. To combat this, you might have to adjust it to its proper position every time it swings around your finger." Hopefully, once spring rolls around, it'll fit perfectly.