Men's Dating

10 Valentine’s Day Scenarios to Avoid

David Wygant

Written by: David Wygant

David Wygant

David Wygant is an internationally-renowned dating and relationship coach, author and speaker. To find out more about David and all of his dating and relationship-building products, visit

Edited by: Lillian Castro

Lillian Castro

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Valentine’s Day. A day many men dread but most women wait for with great anticipation.

When it comes to Valentine’s Day, a lot of men think they can just make dinner reservations and call it a day.

Many men see Valentine’s Day as no more than a “Hallmark holiday.”

The majority of women, however, attach a lot of importance to what their guy does (or does not do) on this day. So as a guy, you don’t want to do it wrong.

Here are 10 Valentine’s Day scenarios to avoid if you want to be sure you will have a happy woman next to you this Valentine’s Day.

1. Know your flowers.

Before you ever go to buy flowers for your girl, you need to know some key information.

Of course, it is important to know what kind of flowers she likes. One of the biggest mistakes to avoid, however, is sending her any type of flowers to which she is allergic.

If you just started dating and you want to send her flowers, make sure you know ahead of time whether there are any flowers to which your girl is allergic.

If you don’t, then she will spend the day sneezing.

Even worse, if you send those same flowers to which she is allergic to her office, all of her co-workers will be asking her whether you listen to her or pay any attention to her, and you will be quickly thrown under the Valentine’s Day bus.

2. Research before you reserve.

If you are planning on dinner reservations being part of your Valentine’s Day plan, then don’t just pick any random restaurant at which to make the reservations.

You always want to research any restaurant at which you are considering making a Valentine’s Day reservation.

You want to find a great romantic restaurant.

A lot of guys will just pick a restaurant about which they have heard good things, only to arrive there on Valentine’s Day with their girl and find it filled with screaming children and video game machines (or something equally unromantic).

This is Valentine’s Day, so make sure the restaurant you pick serves her favorite foods and, especially, her favorite dessert. If you don’t know her favorite dessert, ask her ahead of time.

The more you plan out this day ahead of time, the more special it will be for her and the more special she will feel.

3. Avoid fast flowers.

In addition to being really careful about what kind of flowers you buy for your girl on Valentine’s Day, you want to be equally careful about where you buy them.

The guy selling roses from the middle of the intersection may look like a convenient idea, but chances are half of the flowers will be broken or wilting before they even get put in a vase.

If this happens, you will not look like the romantic guy. You will either look like the cheap guy or the guy who forgot to buy her flowers and had no other choice but to grab flowers on his way home from the guy on the freeway off ramp.

Either one of these will mean a very unhappy woman with whom you’ll be spending Valentine’s Day.

4. Know where your animal has been.

If you are thinking about getting your girl a cute stuffed animal for Valentine’s Day, then be sure to be careful about where you buy it.

I can speak from personal experience on this one. About 20 years ago, I had planned nothing for Valentine’s Day and had to find my girl a present somewhere on my way home (since she was waiting for me there).

I saw a guy on the corner who was selling teddy bear stuffed animals with a little heart that said “Happy Valentine’s Day” on it.

I thought I was lucky and found something great.

When I brought it home, I held it in my hand and knocked on the door. My girl opened the door, and our golden retriever jumped up and grabbed the stuffed bear.

I thought that was very strange and out of character for her, until I realized there was something my dog was smelling that made her jump up and grab it.

It turns out there was some kind of animal scent on the teddy bear and the guy from whom I bought it found the stuffed animals he was selling somewhere on the street.

So be careful where you buy things.


“Consider Valentine’s Day as the Super

Bowl of women’s romantic events.”

5. Don’t do Valentine’s Day the sequel.

Few things will sour a woman on your Valentine’s day plans more quickly than running into your ex-girlfriend.

To avoid this, do not take your girl to a place you ever took your ex-girlfriend on a previous Valentine’s Day.

Also, don’t take your girl to any of your ex-girlfriend’s favorite restaurants for Valentine’s Day.

Valentine’s Day is a day which women like to remember. So you want to start a new tradition with your girl.

Pick a place that will be “your place.” That will make her feel very special on Valentine’s Day and give her a great memory.

6. Have a plan.

Never “wing it” on Valentine’s Day. You need to be the one who decides what the two of you are going to do.

Do not just pick her up and as you’re sitting together in the car say, “So what type of food do you feel like tonight?”

Having a plan for Valentine’s Day is really important. It is the one night you need (and are expected to) show your romantic side.

So step up and show your girl you have one, at least on this one special day.

7. Know her size.

If you are thinking of buying your girl lingerie for Valentine’s Day, then be absolutely sure you know her size before you do it. This is really important.

If you buy her lingerie that is the wrong size – whether it’s too big or too small – you will ruin the day in very quick order.

If you come home with lingerie that is too small for her, she will think to herself, “Oh my God, do I look fat? Am I fat? Does he think I’m fat?”

Also, when she attempts to try it on and discovers she can’t fit into it, she will feel completely unsexy and your evening will be ruined.

Buying her lingerie that is too big is equally disastrous. In her mind, she will wonder, “Does he think I’m this big?”

There is almost nothing you can do that is worse than making your girl feel not sexy or unattractive on Valentine’s Day.

8. Respect her diet.

Let’s say your girl is in the middle of a cleanse or is on a diet when Valentine’s Day arrives. She is trying to take care of herself.

Nevertheless, you listen to your buddy who tells you he bought some great chocolates for his girl, and you get your girl a box of those chocolates for Valentine’s Day.

Buying your girl chocolates when you know she is in the middle of that diet or cleanse is telling her you have absolutely no support for her. A woman wants to know you are aware of where she is in her life.

So if your girl is dieting, do not buy her a box of chocolates just because it’s Valentine’s Day. Pick something else that shows her you’re thinking of her.

9. Keep an appropriate budget.

One of the biggest mistakes a guy can make on Valentine’s Day is buying lavish gifts for a woman he hasn’t known for very long.

Say you just met your girl at a party a couple weeks before Valentine’s Day and she said yes to a Valentine’s Day dinner with you. Don’t go overboard at that point.

Do not send her some ridiculously large gift basket to her at her office. Do not show up to the dinner with three dozen roses in hand and have a Mariachi band there to sing her a love song.

If you’re newly dating someone, chances are she didn’t buy you anything. By going overboard, you are not going to make her feel special. You are going to make her feel uncomfortable.

Instead, giving her a simple card or a simple flower will speak volumes to her and will make her feel very special.

10. Don’t blow it off.

The number one biggest mistake men make on Valentine’s Day is not acknowledging it at all.

Yes, I get many of you don’t think of Valentine’s Day as a real holiday or one worth celebrating.

The truth is unless they move Valentine’s Day to Super Bowl Sunday, most guys will never feel about that day the way most women do.

You need to understand, though, it is a very real and important holiday to most women. So don’t let your girl know you think Valentine’s Day is a “Hallmark holiday,” and just roll with it.

It is her day, not yours. So just be unselfish on that day, acknowledge it and make her feel special.

You never want to just do nothing on Valentine’s Day. It is easy to make her feel special.

Start by wishing her a Happy Valentine’s Day first thing in the morning. Never wait until the time you have night time plans, otherwise she may worry you forgot.

The longer you wait to acknowledge the day, the worse your night is going to be and the more insensitive you are going to seem in her eyes.

Guys, we can suck it up one day a year and make Valentine’s Day special for our girls. It is not hard to make this day special for them if you keep these tips in mind to avoid any major Valentine’s Day disasters.

Consider Valentine’s Day as the Super Bowl of women’s romantic events. It’s a day all about her.

Think how you would feel if your girl ruined your Super Bowl party with the wrong food, the wrong beer and the wrong chips. There you would be with your friends and a totally disappointing party.

Think of it that way and you will understand why you need to make Valentine’s Day special.

You will also avoid the scenarios that can cause Valentine’s Day to be a total disaster.

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