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A MAN’S GUIDE TO PROPOSING THIS VALENTINE’S DAY

A MAN’S GUIDE TO PROPOSING THIS VALENTINE’S DAY

THINKING OF POPPING THE QUESTION? HITCHPLANNER TEAM IS HERE TO HELP.

Romance reigns supreme on Valentine’s Day – Love is in the air. If you’re thinking of proposing to your loved one, then be assured there is no better time to do it than on Valentine’s Day.


Use that special Valentines day anticipation, build it until she realises that this is no ordinary Valentines Day, and then drop the question on her at the perfect moment.

Don’t have a reservation? Don’t have a plan? It’s not too late.

Valentine’s day (VD) is the most romantic day, and the best day to propose. Some may think it trashy or cliché, but if done well and taking into account several factors, then there is no better time than Valentine’s Day to do it.

There is that unspoken expectation that romance will occur on valentines day. Her expectation could be direct or low key, but it’s there – we’ve been culturally programmed to think of VD as such. Keeping this anticipation in mind, you can actually take this opportunity and give her the proposal to remember.

Easy peasy approach to a successful and stress free proposal

This can go both ways. You can gently and gradually guide and nurture this anticipation. Begin the day by confessing your love in words, follow it up with cards and notes that outlines why you love her, dress up and have a romantic picnic – the list goes on. Be persistent and build that anticipation. As this is going to be a definitive memory in your lives, put in the time and thought.

The other way, would be to take that anticipation, and kill any hopes. Tell her that you’ll be stuck at work, and secretly reserve a table at her favourite restaurant to surprise her. But this approach is sub-optimal and wastes the opportunity of valentines day – don’t taint your proposal with any negative emotions.

2 ways to win her heart and get her to say “Yes”

1. Work her detective instincts

There are a few ways you can shape her anticipation. You can start in the lead up to VD, slowly build up the words and actions of love. Depending on your girl – you could give her incomplete information as to your plans, let her curiosity work, or if she is an amateur detective then weave in some false flags to throw her off, the phone number of a restaurant, a receipt, anything that will work your detectives mind. Typically a proposal would happen late in the day, why not build up and then surprise her earlier in the day – that way you can share your joy with friends and family later that day.

2. Empathy

The second main point to consider is to take a lesson in empathy. Close your eyes and imagine that you’re her, encountering your grand plan or campaign of love. Ultimately her preferences outweigh anything that you find on instagram. Nor is asking Google and getting some typical proposal plan online. Paris and the Eiffel Tower may look nice, but mean nothing if it’s not her. Consider if she would prefer a private or public affair, how would she feel if you proposed to her when she’s in her pyjamas or with no makeup? Does she need the proposal to be documented? (Guys, this is important!)


Don’t propose without your photographer if you know she will be announcing the engagement to the world.

Carrying this theme on, a lot of us get stuck trying to think up grand romantic plans. This doesn’t have to be the case – your VD proposal just has to be targeted and speak directly to her. So if she has a soft spot for dogs, use dogs. Sentimental? relive the beginning of your relationship, or retrace some of your best moments. Does she value family? Bring them in on your plans – make a short movie that includes family and friends supporting your proposal. Giving her mementos of love are great, but nothing beats the experience you’re giving her – prioritise having a real experience that invokes as many senses as possible to make it as special and memorable as it can be for her.

The Engagement Ring

A final note, do not hide the engagement ring, just don’t. You get on your knee, look her directly in the eyes and confess your life long love affair, and then with your hand place the ring on her. This is the moment to display unwavering confidence in your love. This means that you should be real, even if you cry. So go ahead, you still have time to create the most memorable and personalised valentines day proposal. Use that special Valentines day anticipation, build it until she realises that this is no ordinary Valentines Day, and then drop the question on her at the perfect moment.

Be sure to refine the whole experience so that it fits her perfectly.

To bring this up a notch, take this opportunity and show your sincerity by kickstarting the wedding planning process with HitchPlanner’s wedding planning tool. You can draft out your guest list in just one afternoon and it shows that you are more than ready to plan the perfect wedding with your bride-to-be.

Special Vday GIVEAWAY: ROMANTIC STAYCATION FOR 2 IN SINGAPORE

You could be super lucky this year. #2020luck

We are also giving away 1 lucky couple a free staycation in Singapore!! To enter, here are the details:

  1. Sign up for a free account at HitchPlanner.
  2. Follow us on Instagram
  3. Comment on one of this giveaway post on our instagram!

Good luck this valentines day!

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