• view count-Should You Propose on Valentine's Day? Here's 6 Pros and 6 Cons 14.7K

After Christmas, Valentine’s Day is one of the most popular days for proposals. Agree or disagree, you have to admit that it’s just very romantic to pop the question on such a beloved day. But then again you might be undecided about February 14th proposal…is it overdone? Is it so-yesterday? We’ve come up with a list of pros and cons to helpfully push you to the right decision. Remember, there’s never anything cheesy about how you declare your love...right? 


1. It’s already romantic 

Proposing on February 14th already sets you up for an incredibly romantic night. You could plan for an intimate proposal at home and you’d still get points for popping the question on Valentine’s Day.

2. You’ll remember the date

Guys are notorious for forgetting important dates. Unless you’ve got a great memory, you might struggle with this. When you propose (or get married) on a holiday, it makes it easier to remember. Help yourself out in the long run. 

3. It’s symbolic 

Why wouldn’t you want to start your marriage on the internationally celebrated day of romance? Not only is an incredibly romantic gesture, but it’s symbolic as well. It will show your future bride that you are attentive to details by choosing Valentine’s Day to pop the question. 

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4. You can get creative 

There are so many different ways to pull off a Valentine’s Day proposal. You can plan for dinner at a high end restaurant, arrange for the ring to be brought out with dessert. Or you could plan for a romantic dinner at home! Light candles in every room - and of course, don’t forget the roses.

5. You can plan an epic night or weekend

Who says you have to limit your proposal to one night? Whisk her away on a romantic weekend trip. You can even keep the trip as a surprise. Just tell her what to pack and where to meet you. Wine and dine her all day, and then propose on the last night. 

6. She might not expect it

Since a lot of people do propose on Valentine’s Day, she might not actually expect it. If you want to surprise her, popping the question on February 14th might actually surprise her! 

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1. It’s cliche 

That same pro can also be a con. Proposing on Valentine’s Day can be such a cliche if you don’t do it properly. If you’ve been talking about marriage, she could be expecting it. Plus you might get some jokes from your friends for proposing on such a romantic (and predictable) holiday. 

2. Tough to pull off 

Because she might be expecting it, pulling off the proposal could be difficult. And if you are planning on a romantic dinner, it’s important to make reservations early. A lot of couples will be enjoying dinner out on the town. You can’t wait until last minute to plan a Valentine’s Day proposal!

3. You might not have privacy 

Getting any privacy could be difficult because of the amount of couples out celebrating. If you were hoping for a private and imitate proposal, it’s best to pop the question at home. Or you might have to spend more for a VIP dinner out on the town. 

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4. Poor timing 

If you aren’t ready to propose, don’t feel as if you have to rush into marriage just because it’s Valentine’s day. There’s no sense of rushing into an engagement because you feel like you need to propose on such a romantic holiday. You and your bride to be can make your own special memories when you are ready to propose. 

5. You have to share

You’ll never be able to just celebrate Valentine’s Day. It will always be remembered as the day you proposed. This isn’t necessarily a bad thing, but if you really enjoy the holiday, it will take away from that special celebration of your love. It’s the same for proposing on any holiday. 

6. You’ll make every other guy look bad

When you pull off such an awesome and epic proposal, you’ll make all of your friends look like lazy scum. We’re not exaggerating. If you are in a group of friends and you propose, all of the other girlfriends will bring this up to their boyfriends. This could put you in the dog house with your bros!