Albert Reid

Q & A with Cassie

Dear Cassie,

Last month, while enjoying a night out with girlfriends at a bar on the North Side, I had an encounter with a very handsome man in his mid-40s. He approached me with what seemed to be a pickup line, or so I thought. Despite his good looks, he very unconfidently uttered, “I know you’re really out of my league, but could I at least buy you a drink?” 

Intrigued, I tried to decide if this was  an unconventional yet (in his mind) smooth pick up line or just an attractive guy with zero confidence. Nevertheless, I accepted his offer and let him buy me a drink. As my friends and I were getting ready to call it a night, he asked me out. Despite my initial intrigue (and slight confusion), I ultimately decided not to pursue a future date with him.

There were a few factors that played into my decision, one of which was what I figured to be an actual lack of confidence. Additionally, what left a sour taste in my mouth was his selective generosity. He bought me and him a drink without offering anything to my friends who were sitting at the table with me. Am I being too judgmental? One of my friends said maybe I should have given him a chance.


Maybe Too Judgy

Dear Maybe Too Judgy,

In dating and relationships, confidence definitely plays a crucial role. It’s not about conforming to societal standards or adhering to someone else’s idea of who may or may not be out of someone’s league, but rather about having a sense of powerful self-confidence.

While this man’s approach may have been an attempt to break the ice, he fell short in conveying genuine self-confidence.

Could it have been his delivery? Should his approach have been subtly infused with an underlying confidence along with his humble demeanor? Quite possibly.

When men are aiming to exude charisma, particularly when pursuing potential romantic connections, the substance of their words holds immense importance.

However, it is equally crucial to be mindful of the delivery and execution of these so-called pick-up strategies when interacting with women.

It is crucial for men to approach women with sincerity, respect, and genuine confidence. When authentic confidence is present, the words will naturally flow, and regardless of their content, they are more likely to be perceived as charismatic. In her mind, this charisma translates as having a masculine and an adventurous spirit.

So, while this man’s approach may have been initially intriguing, it eventually revealed certain aspects that didn’t align with your values. The real question to consider is why you are seeking advice while he isn’t. My suggestion to you is to remain open-minded but trust your instincts.

As for him, I recommend always approaching women with confidence and, for the sake of courtesy, if you buy one lady a drink, offer to get drinks for everyone at the table. This gesture reflects gentlemanly behavior, and gentlemen are undeniably attractive.

To the men reading this, please note that while pick-up lines can be funny and playful, I encourage you to take a leap of faith and engage in genuine conversations. Embracing the beauty of authentic human connections can lead to incredible relationships and connections that you may not have expected.



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