The Editors
Your dilemma is very reminiscent of the Danny-Sandy relationship situation. The two of you can “go together like rama lama lama,” but, in your mind, you and this girl are from different worlds. You’re the master of swag while she is probably just a sweet, hard-working girl; or, to keep up with my Grease metaphor, you’re a T-bird and she’s the wholesome new girl from Australia.
However, consider this: you probably don’t like her because she has “swag.” There is something else that makes her attractive. She is a breath of fresh air from the “swag” bros and chicks that you normally hang out with. If you made a rule for yourself to only date (or attempt to date) girls as “swag” as yourself, you need to break it. The amount of “swag” a girl has should not be the only aspect that makes her appealing to you. Perhaps your not-so-swag girl makes you think deeper than you ever have before or she inspires you to be a better human being. Maybe she makes you feel free, or comfortable, when the two of you hang out.
Maybe you have never even talked to her. Nevertheless, the fact that she is not consumed by “swag” makes her appealing to you; she’s different. Think about it this way: trying to potentially date someone with your amount of
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“swag” would be like dating yourself. Would you want to date yourself? Of course not! You want to find someone that complements you, someone that appeals to you and inspires you. To rest my case, ask her out on a date (or just to hang out) if your gut and heart tell you that she is special. The worst that can happen is that she says “no.” Don’t worry though; you have enough “swag” to brush off those rejections if they come your way.