The Worst Valentine’s Date Ever

“He took me to a dive bar, gave me those dumb, chalky little hearts, did shots until he was wasted and, then expected me to sleep with him.”

Love it or hate it, Valentine’s Day is the biggest date day on the calendar, ranking among the short list of occasions where we must go above and beyond for our significant others. Yet, it is astonishing how many people, especially guys, get it all wrong.

If you are planning a date night this weekend, the forgotten rule is to not treat this date like a sure thing. Going out for the $2 vodka special and a bevy of fried bar food is a worse idea than proposing at your best friend’s wedding. That said, you also do not have to take out a loan to make it amazing.

Here is how you make this date night THE date night.

First, dress up.

Guys, if you would wear a shirt to a concert, a football game or a mud run, you need to change clothes. There are really three things to consider. Your shirt should have buttons. Your pants should require ironing and your shoes should be polishable. If you can check all of those things off the list, regardless of your personal style, you are off to a great start.

Ladies, remember that dress you wore when you were single and trying to find a relationship? Wear that. Shoes and all. I am not one to suggest the style for a woman, but if I tell your man to dress up, you better do the same.

Put some thought into the date.

It is a fact that most people are more enamored by the thought than the price. If you are eating, which you should, you will need a reservation, even at the modest of restaurants. It should be a restaurant and not a bar that serves food. It is the busiest night of the year for a table for two. Call ahead, make a reservation and be prepared.

In the same vein, if you choose flowers or gifts, keep in mind that your date should not be expected to carry around your giant vase of flowers all night. Get them delivered to their house, take them in when you pick them up or have a way to leave them in the car.

Possibly the biggest gripe for bad Valentine’s dates is the other person getting too wasted. If you drink, go easy. It’s OK to want to get a good buzz, but even more important that you get home safely and that you remember the night. Take it slow and easy.

Another good attempt at being a better version of you is to make it personal.

Giving generic everything does not make your mate seem special. Be it a written note, a special dessert, a meaningful location or just something you do not normally do, the impact will be much stronger than if you just hand over the stuff they had at the store.

Be that person from that movie that did that thing that made them cry.

Punctuality is also vital on Valentine’s dates.

Your whole day should center around what time you have to be ready to go. Showing up late is not an option. If you start off on the wrong foot, it is nearly impossible to make up for it later on. You send a strong message that this is just a thing that you have to do.

The last tip for a successful date weekend is to never, ever, under any circumstances meet up with all your friends on a Valentine’s date.

Your crew is going to have to take the night off. They should not see you. They should not text you. They should not be an option. This date is one on one. Period.

In order to be a good friend as well, your only back-up plan for a date gone wrong is to go home alone. You cannot crash someone else’s date night. Make your date the priority, have fun and keep things real.

The worst way to make the night or person feel special is to meet up with a group of people on the day you set aside to share some quality time. Just take this off your list of options.

While I am certain that a lot of people, even us clueless guys, plan and execute great date nights this time of year, there are some that miss the mark every time. That is why there are stories floating around the social circles about careless attire, haphazard plans and drunken debauchery on the night of love.

If you happen to be in the annals of “worst date ever” there is still hope. Just pick yourself up and make this year the one where you totally redeem yourself. Cheers!