Dating Dilemma: To Valentine or Not To Valentine?

Fellas, we have all been there, you met a girl back in November and you’ve been spending a lot of time with her. She’s pretty, smart, and just the right bit of crazy (I like em with a little bit of sass and a dab of crazy). You feel like just maybe you can keep her around for longer than the 4.6 weeks you normally keep your tinder/bumble/okcupid victims alive. Valentine’s Day is coming up, and she has told you that “Hey you don’t have to do anything, Valentine’s Day isn’t that important to me.”

Love is a beautiful thing…

Fellas, there are three great lies that trap men everyday. Take heed and lest ye be deceived:

  1. The Devil doesn’t exist.
  2. When a woman says “I’ve never done this before.”
  3. When a woman says “She doesn’t want anything for Valentine’s Day, it is just another

    What your girl going to look like when you do nothing for Valentine’s Day.

The only way number 3 can be true is if she has never had social media, doesn’t watch tv, and has no friends. Between all of those mediums the average person is bound to feel some type of way if they’re dating somebody and don’t get even a simple “Happy Valentine’s Day” text. Can you blame her? With all of the messaging about the importance of V-Day, it’s hard not to feel a little insecure if you don’t have someone on that special day, and maybe worse if you’re seeing someone and they don’t think you warrant any special attention on that day.

A bit of an anecdotal story, back in the Winter of 2011, I was dating a young woman who told me not to do anything for Valentine’s Day. I’m a bit naive at times and take people at their word, so on Valentine’s Day I texted her “ Happy Monday”. She never replied and unfriended me on Facebook. Last I heard, she was married to a gentleman from Alabama.

Gentlemen, you can only lose if you do nothing on V-Day for a girl that you’re feeling:

  • If you do nothing, and she likes you then she will think you’re not serious about her = L
  • If you do nothing and she’s unsure about you she will be more swayed to think that
    you’re wasting her time = L
  • If you do nothing and she doesn’t like you = W/L only because you spent 4.6 weeks with
    a chick who didn’t even like you meaning you lost time and money.

By my count that makes you 1-2, or basically the Cleveland Browns of Romance. At this point you are left in a conundrum, what’s a guy to do?

So about Valentine’s Day?

You like her but you may or may not like her like “that”. So I’ve created a 2×2 chart to make your decision easier. I believe that many men will find this chart a helpful and an accurate depiction of what to do this V-Day.

  • Lower Right Box: This box should be grayed out, because there is no reason as to why you would be having romantic thoughts about an individual in this box. If you find yourself in this situation, you may need to rethink the choices you have made and are making in life. Perhaps see a therapist?
  • Lower Left Box: This is the zone you put a women whom you find attractive in terms of personality but who is lacking what the French call “je ne sais quoi.” She could have sharp elbows or she puts hot sauce on her broccoli, regardless of the reason, this woman is in the friend zone and you shouldn’t be wasting your money or her time by entertaining ideas of a romantic relationship.
  • Top Right Block: This is a tricky situation, because either you’ve decided she’s not “The One” or you’re not sure. If you do too much she’ll misread it and either think the relationship is more serious than it is and raise expectations or scare her off if she is still feeling you out. My advice here is simple, a simple “Happy V-day” text, should suffice. At that point, you’re not raising the stakes, and you live to fight another day.
  • Top Left Box: If you find a woman in this category, you should probably do something really nice and thoughtful, especially if she’s feeling you too. If you’re not sure of her feelings then go with a box of chocolates and a card. If you’re sure the feelings are mutual, my go to move, in this scenario would be flowers at work, a nice dinner at a semi-decent restaurant (home made dinner if you’re domestically inclined), and maybe her favorite show or a romantic stroll. Game. Blouses.


All of this being said do what you’re comfortable with but too many times I see guys doing the most for a woman who does the least. Unbalanced relationships are unhealthy relationships. If you’re going out of your way to do something special, make sure she is doing the same. If she’s not then let her loose, there’s always somebody better, smarter, prettier, cooler, etc  who will think you’re worth the effort and thinks you’re as super dope as you think you are. In the meantime if you have a side chick make sure you show her some love tomorrow, cuz side chicks need love too.