Ask Shan Tell'emJET Love

Ask Shan Tell’em: The Insecure Girlfriend

Dear Shan Tell’em,

I recently started dating a woman who I have grown to care for deeply. She is perfect in just about every way except for the fact that she has been hurt a lot. She has a lot of insecurities, and does not like me hanging with my friends, male or female. I think she is worth it, but no matter what I do, she just doesn’t seem to trust me for real. We have been dating for three months and I can see myself marrying her. How do I show her that I am worthy of her trust?


Dating an Insecure Girlfriend

Dear Dating,

I’ve got some news for you. There’s nothing that you can do to show your girlfriend that you are worthy. Some of the most faithful, genuine, honest people have their character questioned no matter what they do. If a person has a preconceived notion about you, or in this case is blinded by the pain of their past, then that is all that they will see. At least until they take the blinders off. No matter how much you can see her potential, until she is ready to give you a fair chance—meaning, to judge you based on your actions alone—the relationship will not work.

My advice is to have a conversation with her and switch the dynamic. Instead of operating in the motion of “How do I show her that I am worthy?,” let her know that she needs to start treating you how you deserve to be treated. Communicate to her that you will no longer pay for the sins of others who have hurt her, and that if she truly values you, she will see and treat you for who you are. Loving a damaged woman is tough and trust takes time to build, but the only way to build it is for her to actually trust her own intuition. Until you break that trust, she has no reason to look at you via side eye.

Good luck and I wish you the best.

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Shantell E. Jamison is a digital editor for and  She’s also a radio personality, and cultural critic. Her debut book, “Drive Yourself in the Right Direction: Simple Quotes on How to Achieve Your Best Self” is available now at