Awkward Dating Moments

Awk Sauce – Episode 1

I’ve had my fair share of relationships, some good, others bad. Some serious, others not-so serious…but regardless of the relationship, I almost ALWAYS have had at least ONE awkward moment with every man (let’s be honest, they’re usually ‘boys’) I’ve ever dated. Here are some of my favorites:

**Disclaimer: If you’re one of said men listed below, sorry for being so awk. Hope you don’t mind that I’m using our past to launch myself into Blogger stardom. And by ‘hope you don’t mind’ I mean I don’t care. 

Me dating:

Bow Tie Guy

I briefly dated a guy that wore bow ties as every day wear. You’re probably thinking, “and you dated this guy..why?!” well..because he resembled Leonardo Dicaprio, was older and distinguished and honestly anyone who has the balls to rock a bow tie deserves a fucking shot.

I don’t really recall any super awkward moments between him and I, other than the time I went to his condo and discovered he kept a mannequin in his closet. Like, that he dressed up. He said its name was “R Kelly” because it was “trapped in the closet” – I instantly found that acceptable. It didn’t end up working out because we “wanted different things”

The Diabetic

This guy was awesome. He was super funny, down to earth and I honestly had a lot of fun on our first date. Until he walked me out of the restaurant to put me in a cab and I proceeded to eat shit and face plant into the middle of Boylston.

He of course helped me up, only to discover that I had ripped my tights and was bleeding profusely from the knees and forehead. He was an absolute doll, and ran back into the restaurant to get me napkins and band aids. I noticed he had blood all over his shirt and I was mortified. I began to apologize but could tell he was annoyed, so naturally thought the only way to recover from this was to make an AIDS joke.


Me: Oh no, you got blood on your shirt..I’m SO sorry!
Diabetic: It’s okay..not a big deal (visibly annoyed)
Me: Okay..well I’m really sorry….and like, I don’t have AIDS or anything soo

Really? So now I’ve not only just bleed all over this guy after knowing him for a mere 4 hours but now I’m talking about an immunodeficiency virus that literally almost wiped out all of the 1980’s. Now I’m embarrassed, which means I’m nervous, which means I ramble.

Me: Yeah. Sorry, that was awkward, I just meant that I’m sorry I bleed on you, I’m really bad with blood. And needles. Like I would literally die before I got a shot.
Diabetic: I’m a diabetic..

I gave up and went home.

Surprisingly, we dated for a few months and had a lot of fun together. Also, since he had blood sugar issues he always had candy (side note: Gentleman – no matter how weird or unattractive you are, candy will always get you at the very least a hug, and if you are in fact weird and ugly then lesbianhonest dropping $1.99 on a pack of lifesavers is your best investment since lotion and tissues).

Ultimately, The Diabetic and I didn’t end up working out because I was too busy wasting time with a Zac Efron/Brian Austin Green look-a-like who sent me surprise presents in the mail. Whatever, act like you wouldn’t have left The Diabetic and his Starbursts for a shot with your 90210/high school tween crush..



We’ve all had the whole soldier/marine/navy/hot guy in camo that likes automatic weapons fling at some point in time in our dating career. One, in particular, was fun for a while but was more into planning the zombie Apocalypse that he’s SURE is upon us and gaming with his military bro’s than actually acknowledging my existence.

I wouldn’t necessarily say we had any awkward dating moments, outside of my 4 year old niece being creepily obsessed with him. Her and I are absolute besties, so she tends to like whatever I like, do what I do and dress like me (she’s super smart). But for some weird reason, she was OBSESSED with this guy. He literally almost never spoke unless it was about killing something and ran in the complete opposite direction whenever she was around.

The first time she ever met him, she came strutting into the room wearing nothing but a pair of kitten heels, called him the wrong name and offered him cookies. She’s a fucking genius. I even overheard her once on her pink plastic Barbie phone planning an imaginary trip to Martha’s Vineyard with him.

Nintendo-No-Friendo and I didn’t last very long because I prefer human interaction over virtual ones and I annoyed the living fuck out of him. We’re totes good friends now, though. To this day, when I bring a new guy home my niece will just look at the new guy with a blank stare and whisper “You’ll never be Nintendo-No-Friendo” and walks away. She’s my idol.

I totally have more awkward dating moments to share, especially as I hopefully get more dates (though probably not after people read this shit). But bottom line, I’ve learned a lot from my past relationships. Mostly…

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Twitter: Hippie - Insane Tony

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