My Top 5 Most Awkward “Um…I Don’t Know How to Take That” Moments

Today in America, we celebrate a man who hopped on a ship to find a better way around the tip of Africa. However, he went the wrong way, landed in a strange, rural land amongst a group of locals, and told them he came from a place called Italy in the name of a place called Spain and had now “discovered” them.

Much like those natives probably felt, there have been things said to me in my dating life that have made me scratch my head and go, “Lol what?”

I am not always a tactful person. I think I have made that pretty clear. To the point where I’ve adopted the role of the listener in all of my friendships, and try to keep my words very calculated when the time comes. I have also dated some not-overly-tactful people. And here we have further proof that double negatives don’t work in psychology. –Tact+-Tact=Compliments+Offense=Um…I don’t know how to take that. (Write it down because there will be a short quiz at the conclusion of the post. Also, I’m pretty sure it was on the GRE.)

Here is a listing of the highlight reel.

5. Him: When I first met you, I thought you were the cute and innocent type. But that’s not true, is it?

I get this a lot. People often don’t know what to make of me. I look like I’m 17, sound like I’m 52, and don’t know how to hold a conversation about normal things. The combination just contributes to my awkward. The thing here is that he didn’t elaborate. Did this make me a good witch or a bad witch? What was my type, then? Does this mean I am not cute and guilty? Like a criminal? And not even a cool criminal, but the kind who gets caught and thrown in jail and never attracts the stereotypical attentions of the other criminals because of her not-cuteness but behind her harsh exterior, she just wants to feel loved, dammit? Or was it his way of saying I’m sexy and worldly? I never learned.

4. Him: I feel like you’re the kind of girl people date.

Great so…are you asking me out on a date?

This was before I understood the hook-up culture I was growing up in. I thought that dating was what people did after they had pleasant conversation and exchanged numbers at parties. I didn’t realize being “the kind of girl people date” in college pretty much completely benched you during tonsil hockey season. Also, does anyone else see that this almost contradicts what I was told by number 5? WHO THE HECK AM I, ANYWAY?!?!

3. Him: The first time I saw you, I thought, “I wouldn’t say no.”

Thanks, I guess? I mean I suppose his not ruling me out right away is what allowed us to get to know each other better and date for a bit. But even just an, “I thought you were pretty,” or, “You seemed interesting,” are very nonchalant comments that would have sufficed. I guess it’s good to know I’m not repulsive, but what does a “not no” mean? That as long as I shave my legs, I only kind of resemble a yeti?

To recap, so far we have learned that I am a not-cute, not-innocent dateable distant relative of Sasquatch.

2. Him: I’d say you’re in my top 3.

Out of how many? Top 3 what? If your top 3s are anything like my top 5s, we may have a problem here.

  1. Him: Out of 100? I’d give you an 85.

This actually isn’t a bad score, especially if a 100 is like Grace Kelly or something. But at the time he was my boyfriend of 3 months or so, and I’ve always been a bit of a Hermione Granger type about grades. A B would bring down my Girlfriend Point Average significantly.

As I write all of this, I realize I guess I go for the candid type.

Also, I think my life’s goal is for Columbus Day to be replaced with Awkward Day, when everyone can have a day off from work in the name of all that is awkward. Because that’s what America is really about.

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