Red flags Vs. Fear

Charlie’s Toolbox
5 min readApr 4, 2021


We’ve been hurt before, but as women, we are told it is our fault. So, we analyze every part of the relationship looking for the places where we went wrong. We go over the relationship. We search for the 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 in 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 a directed question. However, scrapping through every sentence, every pause, every non-call, and every ambiguous text is exhausting and quite frankly a waste of your time.

To take the pressure off of you and 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 that women are chosen only if they are virgins, likable, and submissive. So, like many, 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 and over-diligent. To get over that hump, I’ve outlined some tips to keep your imagination, sanity, and love-life in check.

1. Trust yourself and trust your boundaries. In the past, you weren’t clear about your needs, but now you are. You don’t have to be afraid because you know that if your rule-breakers are crossed, you will leave. You aren’t nervous to date, because you know if you aren’t feeling it, you will end it. All the times you over-extended yourself, over-liking a guy, and overprotecting yourself is done because you trust that you know yourself and your boundaries.

a. By knowing yourself, I mean being in touch with how you feel and accepting your feelings as truth. If your stomach turns, and you can’t quite put your finger on it, you know it’s ok to end with your potential. If every time you talk, you feel like you are being guided, then you are ok with ending it with the guy. You don’t explain away your emotions, or make yourself wrong or bad for them. The only thing you do is honor them.

b. By trusting your boundaries, you are saying to yourself there are a set of rules that I made for myself to keep me safe, happy, and comfortable. I tell everyone I meet these rules, and when they agree to a relationship with me they agree to these rules. The moment that they violate these rules, I will leave.

2. Red flags are not tricky. Men like to talk. Men put their feet in their mouths. Men are 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.

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.

3. 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.

4. 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, choosing dates like museums or restaurants is no a red flag. It is miscommunication and once he knows, he can tailor the dates to you.

5. 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? Or Am I combing through each word because I am anxious and afraid of being hurt? If you think the latter, you need more therapy or self-education to help you get to a place of confidence within yourself.

Pain, shame, and embarrassment are 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.



Charlie’s Toolbox

Think less about men and more about yourself! @charliestoolbox on Twitter and IG <<<Charlie’s Toolbox Podcast on Itunes and Spotify>>>