Planning A Memorable Valentine’s Day: A Gentleman’s Guide

With the lovers holiday right around the corner, I figured it was time to offer some assistance to those boyfriends, fiancees, and husbands who need some guidance. It doesn’t matter if you’re in your first month of a relationship, or have been married for a decade. When it comes to planning a memorable Valentine’s Day, no guy wants to botch the romance and risk Cupid’s (or their lovers) wrath.

  1. Plan ahead
  2. Setup a tradition
  3. Start in the morning
  4. Surprise your lover
  5. Remember the little things
  6. Finish with a bang

So, we’re going to cover how to plan a memorable Valentine’s Day from concept to completion. If you go about it correctly, not only will your significant other be thrilled, but you’ll have a roadmap to successful Valentine’s Day plans in the future. Follow these 6 steps to really tug on your lady’s heart strings.

1. Synchronize Watches – Plan Ahead and Setup Alerts

Valentine's day calendar

Gentlemen, please take note of when this article was originally published. At the time of this writing, it is more than 6 weeks until Valentine’s Day. Planning a memorable Valentine’s Day starts well in advance of February.

If you want to set yourself apart from the herd, you’ll need to begin planning early. In fact, I recommend you begin thinking about your romantic exploits around Christmas. However, at the very least, you’ll need to begin focusing your efforts around New Years.

Set dates for when you want to have things completed. Remember, you’re not the only man out there trying to woo their partner come February 14th. Trying to make last minute reservations at a quaint restaurant on Valentine’s Day eve is sure to backfire. Furthermore, local flower shops will be swamped with requests for bouquets of roses as Valentine’s day approaches.

Work Around Your Lovers Schedule

Having a lover who is busy climbing the corporate ladder can make it difficult to lock them down for a candlelit Valentine’s dinner. Make sure you coordinate with their schedule when selecting your reservation times. Doing so requires some forethought on your part, and thus the reason for this section. At the very least, ask your better half to block off their schedule the evening of Valentine’s Day. If you want to keep the allure, ask them to be home by a specific time to make it easier to make your reservation time.

2. It All Starts With Tradition – Setup A Tradition

Alright, so to make the night unforgettable, it’s good to put some thought into everything. However, the Valentine’s Day dinner is arguably the most important event of the day. For that reason, I recommend using this as an opportunity to ease your planning in future years.

I am a fan of choosing a local restaurant as your Valentine’s Day dinner venue. There’s nothing wrong with choosing a chain like Ruth’s Chris instead. However, I don’t recommend choosing a place your significant other goes with her coworkers or friends for lunch. Therefore, avoid the Applebees, TGIFridays, and Uno’s of the world if you enjoy being alive.

Once you’ve scouted the right location, make a note of the restaurant. As the years pass you’ll build up a report with the owners. Furthermore, making repeat reservations year after year is romantic. You’ll build lasting memories. You’ve created your own Valentine’s Day tradition.

Choosing A Restaurant For Valentine’s Dinner

For couples who tend to travel for work, a chain restaurant is probably your best option. If you plan to meet up near an airport, or are traveling to meet your significant other for a romantic dinner date your options may be somewhat limited with regard to setting up a restaurant tradition.

If you tend to stay in town on Valentine’s Day, finding a local eatery is your best bet. Furthermore, you can sometimes find restaurants that have modified dinner specials on Valentine’s Day. This will help you when budgeting for the day, and ensures you and your partner won’t be waiting for endless hours for your food.

3. It’s Valentine’s DAY, Not Just Dinner – Start In The Morning

romantic breakfast in bed

Remember that Valentine’s Day is not just about the dinner. Although I stressed the importance of this portion of the evening in the last section, it is by no means a substitution for the rest of Valentine’s Day. If you really want to make sure Cupid’s arrow finds its way to your lovers heart, start with breakfast in bed.

This doesn’t need to be anything extravagant, a basic Valentine’s day breakfast of eggs, bacon, and coffee is sufficient. Of course, if you’re a culinary artist, then have at it. Make her a Valentine’s breakfast that Gordon Ramsey would be jealous of. However, if you are more likely to start a fire in the kitchen than successfully scramble the eggs, perhaps go out and get something.

Even if you pick up breakfast, it doesn’t need to be anything spectacular, coffee and a bagel from the local bakery would probably be fine. Although, to really get your sweetheart to swoon, more effort is required. Take note that “coffee” is mentioned in each scenario…take the hint!

4. Surprise Your Lover

If you’ve managed to set the bar high in your relationship, and breakfast in bed didn’t “wow” your lover, it’s time to step up your game. Here’s where planning in advance will make your life easier.

First, get your spouse or lovers work address. You’d be surprised how many guys are scrambling last minute to get this information. Remember, you’ll need to know the building address, floor number, and office details. Ideally you’ll double-check this info with an impromptu visit a few weeks before Valentine’s Day.

Don’t insult your lover by asking the day before what their work address is, they aren’t stupid. Also, doing so cheapens the experience. There’s nothing worse than having your significant other believe you are doing these romantic gestures because you “have to” rather than you “want to.”

Flowers vs. Chocolates vs. ???

chocolates, flowers, and other valentines day gifts

Alright, as you’ve guessed it’s time for a surprise delivery. But what do you send? There are always the classics, like a dozen red roses or any other bouquet of flowers. If your sweetheart has a sweet tooth, you can opt for chocolate. You can even send the cute cuddly teddy bear if your lady is into that. However, it’s really up to you what you send. Actually it really doesn’t matter what you get delivered to the office on Valentine’s Day.

In all honesty, the best part of this is the humble brags your significant other will have access to in the coming weeks. In all likelihood they’ve already talked about the breakfast in bed you’ve managed to conjure up. Getting flowers delivered to the office on Valentine’s Day is just the icing on the cake. Your lovers head will be swimming with thoughts of what’s to come, and no doubt their coworkers in the office will be jealous. Mission accomplished.

5. Remember The Little Things – Be A Gentleman

be a gentleman, like superman

For those of you who have found this article in advance of February 13th, I have the utmost confidence that this is step is already ingrained in your head. Do all of the little things that make your lady’s heart melt. Here’s some common gentlemanly actions that have gotten lost over time:

  1. Open the car door for her
  2. Hold the door and allow her to walk in first
  3. Help her with her coat (both on and off)
  4. Pull out her chair at dinner
  5. Hold her hand when you’re walking

I’m sure that I’ve left a few items of this list, but you get the general idea. Pretend it’s a first date and you’re aiming to impress her with your charm, whit, and manners and you should be just fine.

6. Finish With A Bang!

Alright, if you’ve managed to complete all of the steps above, then it’s time for the coup de gras of the evening. Perhaps it’s dropping a really special gift that you found that perfectly sums up your relationship. Maybe it’s taking your S.O. home for a special dessert that you actually prepared (looking at you culinary gurus out there). If you end up at a bar with live music, maybe slip the musician a 20 spot and ask him to play your song (or at least something romantic) to finish off the evening.

Whatever your choice, this is the time to go over the top. Romance is the name of the game, so take notes from those Hallmark movies she’s always watching. Be warned, this last step definitely sets a precedent for next year, but I’m sure you’ll come up with something to top it. After all, you’ve got a whole year to contemplate how to make the next Valentine’s Day better than the last.

Looking For Love This Valentine’s Day?

Are you still searching for that someone who completes you. No worries, I’m glad you arrived at this article. However, you’re likely still in the puppy love stage of your relationship, and maybe even getting ready for your first date. If that’s the case, you likely don’t have the timeline to accomplish everything on this 6 step tutorial.

Before you jump head first into your initial encounter, I recommend you read this article about gifts and first dates. If your first date happens to fall on Valentine’s day, you’ve got to strike a balance. You don’t want to set yourself up for failure in the future.

Going overboard with the romantics, may scare your new beau away. Don’t do enough and she’ll think you don’t have a romantic bone in your body. Remember, you have to make to date number two before you reach forever.

I Waited Until The Last Minute, Now What?

Tsk Tsk. Well I can’t say I blame you, it’s not like you’re the first guy to ever procrastinate when it comes to Valentine’s Day. Fortunately for you, I’ve written another article about your current predicament that should get you by this one time.

However, before you click onto the next article, do me a favor and bookmark this page. Even better, give this page a share on your favorite social network to spare your fellow man your fate.

Although you’ve expedited your timeline by waiting, your last minute plans don’t need to be anything less than impressive. However, you’ll need to do a lot of legwork yourself to make Valentine’s Day memorable. Also, your wallet may take a hit in order to make an impact.

Final Thoughts

Remember, that the key to a memorable Valentine’s Day is careful planning. Get out in front of this holiday and make your reservations early. Plan to have gifts delivered well in advance of your date night. Always keep your partner guessing, and keep the surprises coming. Finally, remember to always be a gentleman.

If you’re careful in your choices, you’ll be setup to have memorable Valentine’s Day’s for the foreseeable future. Gifts can definitely help, but as the old adage goes; “It’s the thought that counts.” Here’s hoping you have a wonderful and memorable Valentine’s day for years to come.

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