How I Ruined Valentine's Day and 5 Things to Learn from My Mistakes

With Valentine’s Day rapidly approaching, it’s time to start doing some thinking to make sure this one is one for the books, and only in the best way possible. The long-standing perception that men are bad at making Valentine's Day (and holidays in general) special frequently pops up in TV shows, movies, and other popular culture in a hilarious way. But when it happens to you, it's not so funny. I'm here to offer some advice to blow your significant other away this Valentine's Day.

I’m a firm believer in the idea that you should always learn from someone who has already had successes or made mistakes so you can learn from them in a fraction of the time that they did. This Valentine’s Day my gift to you is to share a failure I had a few years ago, (and still live with to this day), and review what I learned from it so you don’t have to make the same mistakes.

First, a little background.

Two years ago, in my sophomore year of college, my girlfriend (Sarah) and I had planned a special night out for Valentine’s Day. Sarah offered to take us out to a new, undisclosed, restaurant as part of her gift to me. Knowing that we would be exchanging gifts, I decided to plan ahead and order her a watch and a necklace. The watch was a bit of a risky item, because she has very small wrists and most didn’t fit her, but I was confident this was the right one. The necklace was just something small I saw on the same website and decided I would throw in as a secondary gift.

The big day came around, and I had work until 8:00pm (which was my first mistake). I got off work and ran home to find Sarah sitting in my room with rose pedals all over the room, sticky notes covering my walls, and gifts on my bed. This I when I knew I was in trouble; it was the most thoughtful display I had ever seen, and I hadn’t even bothered to wrap my gifts to her.

The sticky notes on the walls were cut into heart shapes and written on them were inside jokes and clever little sayings explaining how much she cared about me in ways that alluded to my favorite TV shows. I keep them in a plastic bag in my desk drawer to this day. The gifts on the bed were clothes items I could wear out to the dinner she was about to take me to – Calvin Klein briefs and a maroon bow tie to match her dress.

Now it was my time to give her the gifts I had hidden in my closet for months inside a shoe box. This is where things get bad. I reached up to the back of my closet and pull down the shoe box and handed it to her. She opened it up to find a necklace balled up in the corner, and nothing else. I immediately started frantically searching the room to find the watch I had pulled out to look at only a few days earlier to no avail. In fact, after many deep cleanings and two moves, it has never shown up to this day.

Sarah is very understanding and kind, but she places a lot of value on holiday gestures, and mine paled in comparison to hers. I felt awful, she had done so much for me and I thought I had done enough, and in the end I had even less to give than I thought. Now obviously it's the thought that counts, but when you toss a necklace into a shoe box and hand it to her, you lose all hope of that adage working in your favor.

So what can you learn from this story?

There are so many things wrong with this story, it's ludicrous. Below I'll break them down into 5 things you can take away from it, and hopefully improve this Valentine's Day for all parties involved.

Plan Ahead

The one thing I did well in this story was plan ahead. I purchased her gifts a few months early, which actually saved me a lot of time, money and stress. But what can you do to effectively plan ahead?

What I like to do is keep a running list of anything she says she likes throughout the year when we're out shopping, when she's browsing Pinterest, or any other time she sees anything she likes. This way, when it comes to a holiday or just anytime I feel like doing something nice, I can pull up the list and know she'll love what she's getting. 

Planning ahead also has the added benefit of being able to scope out the best deals. When you know what you're looking for, and you see it on sale in July you can pick it up for cheap and hold onto it until the next holiday.

Make Time a Priority

It's no secret that couples that spend time together are closer, have more open communication and just generally are happier. On holidays especially, the time you spend together is when you create memories that will last the rest of your lives. The beautiful part about Valentine's Day is it's a day to celebrate spending that time together and appreciating each other.

If you just can't take time off of work, like I couldn't, make the time you do have a priority. You can eat breakfast together, share a shower, or even just wake up a bit early to lay in bed awake together. After work, you can spend the night in cooking dinner, watching movies or going for a walk together. 

Whatever you do to spend time together, make sure it is quality time without the distraction of phones, social media, friends, etc. This is your day to spend time together and grow closer as a couple.

Let the Gifts be a Supplement

As we've grown together as a couple, we've realized a few things about gifts. Firstly, we have pretty much anything we need. If one of us really needs something, we either buy it for ourselves or we'll immediately get it for each other to help out. The second thing we've realized is that the most exciting part about the gifts is the thought we put into it. When you treat the whole holiday as one big set of gestures, the gifts are only a small portion of it.

The problem with our first Valentine's Day was my entire gesture was the gifts that I got her, and when the main gift mysteriously disappeared she was left with just a small gesture after exerting all of that effort to make me happy. And if you look at her example, she got me a bow tie and a pair of briefs. By themselves, these wouldn't seem like the greatest gift in the world, but paired with hours of effort and small tokens of her love for me it was the best gift she could have gotten me.

Do anything you can to make your significant other happy and make their lives easier for just one day, you'll be surprised how far it takes you. (Which leads me to the next lesson)

Focus on the Small Details

On holidays you should pay extra attention to the smallest details. Everything from gift presentation to the little things you're going to do to make the day special. One way I like to do this is to think through every step of her routine and come up with ways to make them a bit more special than usual. I'll give an example using Sarah's morning routine.

Every morning, she wakes up and throws on her robe and walks out to her makeup station to begin putting her makeup on before making coffee. She then sits down to drink her coffee, packs a few things to snack on during work and class, and heads off to work.

What I would do to make it special is wake up a bit early and throw her robe in the dryer so it would be extra warm and hand it to her when she woke up. When she got to her desk, she'd find a hot cup of coffee and a small breakfast with a short but sweet note expressing my feelings for her. She'd look in her bag to find her lunch packed (and since it's Valentine's Day, maybe cut up into heart shapes).

Whatever you do, just make sure that s/he knows you're taking the time to make his/her day better and that you're trying to make the holiday special - all before the gifts are even mentioned! Now you're on track to impress, even if something happens to the gift you got. Continue this throughout the rest of the day with texts, phone calls, flower deliveries, etc. to make it feel even more genuine.

Don't Expect Anything in Return

This mistake was actually made by Sarah, and I think it's really important to mention. She put all of this effort in and was so happy to show me what she had done, but when I didn't have much in return, the day became regarded as the "Valentine's Day from hell." 

When you put a lot of effort into something, be proud of what you've done and expect nothing in return. If you feel like you're trying really hard to make something special, realize that you feel that way because most people don't put in that much effort. Just feel proud of how happy you made your significant other, and how clearly you expressed the way you feel.

Best of luck this Valentine's Day, gentlemen.

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