Valentine’s Day Date-Getting Ahead Planning The Perfect Valentine Date

planning valentine's day dateDon’t worry! Planning a Valentine’s Day Date doesn’t have to be stressful. Men can sometimes sweat the details of putting together and planning a great Valentine’s Day date.

Here’s some simple ideas to guide you as you’re planning a Valentine’s Day date for your sweetheart. Above all else, follow this one principle and you’ll make it great: make it about her, and focus on making her feel special.

Do that, instead of spending oodles of cash trying to impress her. Planning the Valentine’s Day date simply with her at the center of it will continue to help you win her heart.

Buy A Valentine’s Day Card

Don’t start planning your Valentine’s Day date without thinking about what kind of card you want to get. And I encourage you to get something thoughtful.

Make sure you don’t let the card do all the talking—write a nice note yourself.

If you MUST get a humorous card, make sure to buy two—one for humor and one that says something meaningful.

If you really don’t feel in the mood to drop $6 on a card, then write her a hand-written letter. Ladies love handwritten letters.

Buy Her Valentine’s Day Flowers

It pains me to suggest to a man they drop $50 on something already dead. It’s insanity. I don’t get it. But women do. So unless your women knows how much you both are on a budget, or you plan on spending that money on something bigger than flowers, buy her some. Even if it’s just a single rose.

When it comes to Valentine’s Day date planning, get ahead and find out what is her favorite flower. Roses are winners, yeah, but you’re a winner if you know exactly the flower she loves the most.

Check out great pre- and same-day deals on Valentine Flowers

Make Her Gift Special

Is this complicated? Trust me, it’s not. As you’re planning the Valentine’s Day date just message 2-3 of her closest friends  and ask for ideas unique to her. It’s possible you have some great ideas—go ahead and run those by her friends too!

Plan An Experience

Do more than merely plan dinner, dessert and drinks. That’s fine and good, but you don’t have to have those components for the date to be memorable. It’s about making her feel special, remember?

Here’s my list of ideas for Valentine’s Day date planning you can mull over:

  • Before the date, listen to what she’s been saying lately she’d love to do.
  • Before the date, give her a little invitation that keeps her guessing but gives her a sneak peak as to the theme of what you’re going to do.
    • Once I gave my girlfriend multiple “international” invitations. I think I dropped her off to Asia first (yep, it was to get a mani/pedi), Italy for a picnic at a nearby pond with a piece of framed art waiting for her, and France for dinner and dessert at a French creperie. Of course she got her favorite flowers to start the day.
  • Mix in an activity. Throwing coins in a wishing well. Hot balloon ride. Dancing.
  • Don’t just let the card or letter say it. Make a moment during the date to tell her how highly you think of her.
    • Note: If you’re not in love yet, don’t feel pressured by the moment to use the “L” word. You’re not obligated to tell a woman you love her unless you mean it. And, I think it’s wrong to do so.
  • Dinner: you don’t have to spend $100-$200 to make most women happy. Just find a place that you haven’t been before, or something that will at least still feel original and different. You’re creating an experience!
Create At Least One Surprise
planning valentine's day date

Write, or draw, her something nice!

What will knock her socks off? What’s an original idea you’ve wanted to do for a while?

Here’s some thoughts:

  • Memorize a love poem and recite it to her
  • A walk on the beach, or a well-lit park, or a cute part of old-timey downtown.
  • Stargaze
  • Call the local radio station and dedicate a song to her
Don’t Be Stressed During the Valentine’s Day Date

When planning your perfect Valentine’s Day date, don’t get stressed. Get ahead, put together solid ideas and enjoy it. If she’s not having fun and you worked hard to make it great, don’t fret. Maybe her expectations are too high and no man was going to perform the perfect emotional mix of “surprise” circumstances for her anyways.

I’m willing to bet at the end of the day, she just wants to spend time with you, and know that you cared. Having spent the time and effort to put together the Valentine’s Day date will show her you did.

Bring the Focus Back to Her

At the end of planning your Valentine’s Day date, just ask yourself one question: is it about her and will it make her feel cherished? If you can answer “yes” to that, I have no doubt you’ve done a good job and it’ll be a great February 14.

An Extra Note

Some people don’t like being wined and dined and having a big night out on the town. If that’s the case, ask your lady what she likes, and just keep it simple and do that. Maybe all it takes is cooking dinner for two!

Photos by Herry Lawford


  1. I need to show this to W haha 🙂

  2. Good post Todd! I’ve done a lot of these things in the past and still do some of them to this day. We like to keep it low key and just enjoy spending time together without having to rush to get something done. I generally like to prepare a nice meal for the two of us to enjoy and just make it fun for my wife.

    • Something I thought of including in there was being considerate if your significant other likes to keep it low key. Since I’m still in the dating world women still want to be wined and dined. But it seems that that level of maintenance may go down a little as you’re married longer :).

  3. I actually always do humorous cards. Since humor is a strong part of my wife and my relationship, it works. And since humor is something that comes much more naturally to me than romantic, it seems more real as well.

  4. One thing I learned a long time ago was to ALWAYS bring the focus back to her 😉 Great points and your exactly right at the end of the day chances are she just wants to spend time with you. I personally work 10 hour days and we have a little toddler, very rarely do we get time to ourselves.

  5. I hate sappy cards, but a note is very nice. I would vote for the experience over flowers any day.

  6. i just got married before 4 months this is my 1st valentine day with my lovely wife but i confuse what to do—-i think giving flowers is better idea

    • Flowers is always a winner! Definitely do that. But chew on doing the other ideas as well. With this being your first Valentine’s Day together, you don’t want it to fall flat! Make sure you do a couple extra things to make the day about her and make her feel special. Write her a few notes that she gets in the morning, during lunch, throughout the day, etc. Maybe one of the notes has an invite to you cooking dinner or the too of you going out. If you can have flowers delivered to her workplace or give them to her in person there that’d be great. She’ll love that her friends got to see what you brought her!!

  7. A+ post. I love the focus on your significant other. There are lots of other personal finance blogs that I read and love that only talk about how to keep Valentine’s Day cheap or rail against why it’s a fake holiday.

    This is awesome and actionable.

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