How to Get Over Your Fear of Dating

Charlie’s Toolbox
4 min readMar 9, 2020

We’ve all been hurt, and as women, we are often told it is our fault. So, we analyze every part of the relationship looking for the places where we went wrong. We search for red flags and signs that we missed. We hyper-obsess over the details. Then, we commit to never fall for it again. We commit so much, that we become too diligent turning any minor issue into a huge red flag. He didn’t call me back immediately, red flag. He didn’t give me the compliment I wanted, red flag (I am guilty of this). He didn’t answer in the way I like, red flag. Now, it is important to listen to the person you are dating. It is important to figure out this person’s character as soon as possible. It is important to ask many directed questions. However, scrapping through every sentence, every pause, every non-call, and every ambiguous text is exhausting and quite frankly a waste of time.

To take the pressure off of yourself you have to stop thinking in a fear-based way. You did not have the tools before. You came into a romantic relationship with no knowledge of how patriarchy teaches men how to manipulate you. Your parents told or demonstrated to you that women are chosen only if they are virgins, likable, and submissive. So, like many of us, you approached these relationships with that information guiding you.

Unfortunately, you had to crash to realize that the dream they sold was untrue. You had to fall hard to see how deeply ingrained patriarchy is. Once the wool was lifted, you were able to see what romance is and what romance is not, but the pain, shame, and embarrassment of the situation make you extremely paranoid. To get over that hump, I’ve outlined some tips to keep your imagination, sanity, and love-life in check.

  1. Red flags are not tricky. Men like to talk. Men like to put their foot in their mouths. Men like to be sloppy with their conversations. So, if you ask questions if you listen, and if you wait it out, the red-flags will always present themselves. Men aren’t masters of disguises. They aren’t that sneaky. Often, their flaws are loud. The only reason why people are oblivious to it is that people will tell themselves stories about the red-flags to minimize it or create sympathy about it so they can stick around.
    a. For example, you are dating a guy who is demonstrating he is stingy, but he tells you a story about growing up poor. Instead, of taking his behavior as it is and deciding that it will not mesh well with your lifestyle, you create a story to sympathize with him. You tell yourself he is selfish because he never had anything and that you will prove to him you are worthy of his unselfish behavior by proving how giving you are to him.
    This doesn’t make sense. Why would you change yourself to get someone to change themselves?

2. Instead of looking for red-flags, look for character. When you analyze a person’s character, you are looking for the complete picture. You are looking for or creating moments where things won’t go his way. You are observing his behavior and asking yourself, will he keep his head? Will he be ok compromising? Will he be able to put himself second? Will he become angry about it? Those are questions that look at his character. Those are questions that look at the complete picture and not minor actions.

3. Is this misunderstanding something that could be communicated? Meaning is it something that he misread or did not know about you? For example, he may not know that you prefer outside dates so him choosing dates like museums, or restaurants would not be a red flag. It would simply be something that wasn’t communicated to him, and once he knows he can tailor the dates to you.

4. Are you healed? Sometimes anxiety points to places unhealed or shows that you do not truly trust yourself. Ask yourself, am I combing through each word because I don’t have the right skillset to date? Am I combing through each word because I don’t trust myself to leave a toxic situation? Or am I combing through each word because I am anxious and afraid of being hurt? If you think any of the three, you need more therapy or self-education to help you get to a place of confidence within yourself.

Pain, shame, and embarrassment is a part of life. No one has escaped it. No one has lived without it. So, give yourself a break! Stop hating yourself. Obsessing over the new guy. Being anxious or nervous about every interaction. Your nerves won’t help you, but your confidence and belief in yourself will. So, believe that you have the knowledge, experience, and self-confidence to weed out anyone who is not right for you because you truly do.

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Charlie’s Toolbox
Charlie’s Toolbox

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