I Went On A Date With My Sister’s Crush

In the laws of girl code, dating your sister’s crush is a huge, written in big fat red letters NO. But sometimes the world can be cruel and it puts you in uncomfortable situations that make execution by elephant (this used to be a real thing) seem merciful. One of those situations was when I went on a date (the second time) with my sister’s crush.

I’m Not A Terrible Person Right?

Okay, let’s get the elephant – this wasn’t planned but I’m glad it happened – in the metaphorical room out of the way. Yes, I went on a date with my sister’s crush twice BUT the first time I was unaware of her feelings towards him. That only makes me half a terrible person right?

When I first met he who shall not be named it was at party, one for which my sister was also in attendance, and we actually didn’t hit it off at all. But I guess that’s where that whole opposites attract thing comes in? Even though my years as a psych student taught me otherwise, but I won’t get into that now.

Where Are Those Elephants When You Need Them?

After seeing each other at another party we realized we actually had a lot in common (wait, so we’re not really opposites are we?) and we decided to get to know each other better. Naturally, we went on a date. In our case, one date was one too many and we both walked out of there regretting it. Okay, I can’t speak for him but even the most oblivious person would have been able to feel the I’m-uncomfortable-please-get-me-out-of-here rays he was emitting.

The whole ordeal was so absurd and such an absolute waste of my time I never bothered mentioning it to my sister. Yup, that was a mistake. A few months after the long forgotten incident, my dating life was still a calamity. More importantly, my sister decided to show me pictures of “this guy who is SO cute, we actually met him at a party if you remember.” Of course it was him. It was the guy I went on a date with that one time who had me questioning my life choices twenty minutes into said date.

And The Gold Medal Goes To

Okay I could have made this all so much easier if I stopped her then and said “don’t waste your time, been there done that” but for anyone who knows me, they know I’m not exactly the most confrontational person and I avoid uncomfortable situations like it’s an Olympic sport. So I didn’t say anything.

My sister and the long forgotten date of mine started talking to each other and neither he nor I ever brought up our so-brief-that-it’s-barely-there past. I didn’t think there was anything wrong with that especially considering we were all adults.

Did I Say Adult?

A month or so goes by and everything seems to be going great. Until my sister and I got into an argument. It got heated and because I had a serious case of word vomit, I let it slip that she maybe, sort of, kind of was hardcore crushing on my sloppy seconds. Ouch. I know.

As you can imagine, what followed wasn’t pretty. She began speaking in a language that was foreign to her. It was all bitch, no English. Seriously, if bitch wasn’t my vernacular I would have needed a translator. Just to add fuel to the fire I decided to message the ass who created this mess to began with. Alright that’s not fair. Calling him an ass is downright disrespectful to donkeys and the human body.

See Also

10 Things Every Daughter Wants Her Mom To Know

I Went On A Date With My Sister’s Crush (Round Two)

For reasons that I won’t be able to decipher until I’m long past dead, I asked this guy out on another date. Out of all of the revenge plots I had in my mind to get back at my sister this is the one I decided to go with. Yeah, I don’t get it either. Here’s the thing – I know why I asked him out. I was pissed off and trying to get back at my sister. Why in the world he agreed when our first date was a not so epic failure, I don’t know.

I proceeded to go on what was the worst date of my life. The entire time I was miserable because I knew I was there for all the wrong reasons. I couldn’t believe I was on a date with the guy my sister explicitly made clear to me she liked. Most of all, I couldn’t believe she was actually attracted to the douchebag I spent the next two hours discussing bitcoin with. Yes. Bit-fucking-coin.

Sorry Not Sorry

Needless to say I apologized to my sister and she, being a way better person than I’ll ever be, forgave me in an instant. She also told me her and the douchebro hadn’t talked to each other for weeks. So not only was I an ass, I was an ass who played the biggest role in my misery. *Note to self: tone down the theatrics*

My sister and I promised to never mention this disaster to anyone because it’s embarrassing on both parts. So sis, I love you and I’m sorry for this. But not really. 

Have you ever went on a date with someone your sister or someone else close to you had a crush on? Share your story with us in the comment section below!

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