My Top 5 Most Awkward Rejections

Welcome to Top 5 Friday here at J. Awkward Prufrock. Today, I will be discussing my Top 5 Most Awkward Rejections.

We all get rejected romantically at some point or another. I’ve been rejected dozens of times and can safely say I’m pretty immune to it, but it still always stings a little, especially after you spend a good deal of time dreaming up fantasies of how wonderful everything is going to be once you both finally admit your true feelings. Maybe you will have a date for that wedding, maybe you won’t be the sage, yet disturbing neighborhood spinster, maybe you are totally dateable and you just haven’t realized it, but he will! All that build-up only to get your heart broken, but that’s all part of being human and it certainly provides us with many moments to laugh about. Onward, awkward, and upward!

These 5 little moments happen to be my favorites due to several key factors, but mostly it has to do with tact (or lack thereof) and, of course, as always, awkwardness.

Behold…and enjoy.

5. Me: I like you.
He cringes in the way you cringe at a semi-helpless suffering animal and shakes his head.
Him: Sorry.
He walks away at impressive speed.

I was a fan of this one because it was very to-the-point. I had zero questions about what was happening. No dilly-dallying or beating around the bush, no suspending ourselves in the awkward spectrum for any longer than need be. Pure, polite washing his hands of me.

4. Him (on phone): When I first met you, I thought you were really spunky and athletic, but I’ve come to realize that is not the case. Also, you’re kind of annoying and you’re really getting in the way of me figuring out what I want to do with my life. I thought I loved you at first, but now I actually don’t think you’re good enough for me. Also, I want to be able to hookup with other girls while I go on my trip.

I can’t fault him for this. He clearly put a lot of thought into it.

3. He runs out onto the front steps of the building in a drunken, manic state as his ride pulls up.
Him: I’m so happy right now!
Me: What’s gotten into you? Why are you so happy all of a sudden?
Him: Because I don’t like you that much anymore!
He runs and does a bell-kick off the last step before getting into the car.

How nice to have brought someone such joy, if only for a moment. (Really, how many women can say the thought of not being with them caused a grown man to bell-kick?)

2. Him: You don’t want to be with me. I have a small penis.

Ah, the old self-sacrifice. Very respectable. He really threw himself under the bus for that one. Gave everything for the greater good. However, I would like to point out (incase any of you guys out there are thinking of adopting this tactic) that number 5 is preferable to this one. Number 2 here opens way too many doors for conversations about how I don’t really care about that sort of thing, or question like, Are you really self-conscious or are you just trying to turn me off? How small is small? I’m going to move my fingers apart gradually and you tell me when to stop. He ended up stuck with me for another hour because I was genuinely curious about his penis claims.

And finally, the big one, the mother of all rejections, the crown jewel, the head honcho, the Morgan Freeman of break-ups.

1. He brushes his hand over my face before taking it in his hands. He kisses me only once, but it is so passionate, it leaves me breathless. He looks me in the eyes with great depth and profundity.
Him: Someday, somebody is going to love you the way you deserve to be loved.
He leaves and never talks to me again.

I can’t stress how much I admire this guy for the way he handled this. This is some classy stuff right here. He left me feeling absolutely amazing about myself; high as a unicorn making its way to cloud 9. He rejected me without letting me feel rejected. Granted, it did leave me with some confusion about where we stood, but after several days of him averting eye contact and diving behind tables when I entered the university’s cafeteria, I began to get the point.

Have an awkward rejection that tops these? Leave a comment! I would love to hear from you.


4 thoughts on “My Top 5 Most Awkward Rejections

  1. This blog is fantastic. The most awkward “rejection” that ever happened to me was at a party where the guy I was talking to looked at me said “you’re really smart” and immediately walked away. Thank you sir I am, very smart.


  2. When I was probably 15 or so my family and I were on a vacation down in North Carolina. Across the street from our beach house was the most gorgeous girl I had ever seen in my young life. I was instantly in love. For the entire two weeks we were there I sat at the window waiting for her to head down to the beach so that when I arrived I could plant myself as close as possible without being creepy (in hindsight I probably was pretty creepy). Time and time again I thought I had worked up the courage to say hello and began walking towards her beach chair, only to keep walking right on by as I chickened out. Finally, it was our second to last day, and her and I both happened to be swimming at the same time due to a completely orchestrated coincidence. I waded over towards her and finally said hello. Her response? “No hablo ingles.” Not technically a rejection I suppose but I was still scarred for life.


  3. A friend of mine spent some time in Ohio some years ago, and among the church-going guys, a favorite dump line was “I’m sorry, I can’t serve God and this relationship at the same time.” I never heard whether the girls eventually caught on or not.


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