An Anthology of What Could Have Been

This is not going to be very cohesive. I’m not entirely sure why I’m writing this besides to look back on it in a handful of years and reminisce on a time when I was more fun. So, sit back, relax, and enjoy my testimony of dating in my 20’s (unless you are my mom, dad or some dude who dates me in the future; you guys have nothing to see here).

To resolve any confusion about why I do the things that I do, let me start by saying that the part of my brain that harbors shame and the fear of rejection is broken. I lack both of those things. Trust me, it is not because I am overconfident; it’s a lazy form of self-loathing. To make things fun, let’s count how many times the word “DM” pops up.

There was the Canadian I DM’ed (ope there’s one) on Instagram when I was 21. I don’t know what my motivation was, being that he lived in Vancouver and all, but it was like James Franco and Dave Franco made an incest love child and this guy was the result. I wish I could add pictures, seriously. My opening line was… actually you know what, maybe I will add pictures.


Smooth. As. Butter. Yup, that says 1:54 AM. Also, no, I did not scroll three years deep into my inbox to find that conversation. I want to make that very clear. So anyways, my broke ass somehow booked a plane ticket and I met that guy for the first time in an airport. A few weeks later I stopped replying to his texts and we never saw each other again.

One rainy night I met a Swedish man who saw me standing alone outside with a dead cell phone and wet hair. We stood out there, in the rain, and talked for awhile before he ordered an Uber for me so I could go home. He canceled it before I reached my destination so I had to get out and walk the rest of the way. We’re pals now. I visited him in Maine after several months of inconsistent communication.

Then there was the football player in college who invited me over at 11pm once a week. I’m gonna just leave that one as is.

There was the guy from Bumble. Oh yeah, you know where this is going. I was 22, he was 28. Very exciting. He picked me up in his G-Wagon and proceeded to talk about said G-Wagon for the entire drive to the restaurant. At dinner he explained how “everyone’s a liiiiiittle racist.” He tried to kiss me when he dropped me off but I told him I had cold sores. Mhm. We made a silent agreement to never speak again.

On one of the more hungover days of my life, I went to a concert (again, hungover, I took the optional on a shower and makeup routine) where I eloquently DM’ed the drummer of the band, “rock the f**k out of those drums, Dale!” That’s from Step Brothers, mom, I know you’re still reading this. We drank together after the show and had emo talks until my sister thought I got murdered and came to pick me up. For the record, I would’ve let him murder me. In hindsight, that would’ve been a good night to actually, you know, get ready for.

Speaking of DM’s, there was the guy who flew me to Nashville for a date where I drunkenly spilled a full bag of M&M’s all over his apartment and forced him to talk about his feelings at 4 in the morning. We made out at the airport and haven’t really talked since. Coincidence? Definitely.

Let’s not forget the guy who doesn’t remember jokingly asking me to prom in high school in front of the rest of his basketball team, traumatizing me for years to come, forcing me to hit the ground running on Handling Rejection 101. Six years later, I took him home at bar close and blue-balled him out of spite. Not really a date, but a classic coming-of-age tale that I owed my sad, 16-year-old self.

To wrap up this fun narrative, we have the double date with one of my best girlfriends where by the end of the night, both men were competing for her attention and I was just along for the ride and cheap entertainment. Super good time, 10/10 would recommend going on a double date with your hottest friend.

I know I’m going to read this back and remember several more ghosts-of-first-and-last-dates’-past that I forgot to include. But this has served as a reminder to myself that it can be worse, it has been worse, and um… someday I’m going to have infinite wisdoms to share with my kid(s). There aren’t rules. There’s no ~proper~ way to meet someone (although I’m sure I’m to blame for most of my dad’s gray hairs and my mom is sick of my pursuit of men in other states). And dating is supposed to be fun – you’re not going to click with everyone, you’re supposed to look back and laugh at the times you did something really freaking stupid. Maybe, like, don’t put all of it on blast on the internet?? for people who could possibly judge you, to you know, judge you?? But alas, this was the best content I could come up with today.

9 thoughts on “An Anthology of What Could Have Been”

  1. Ok, this story was a solid 7 or 8 out of 10…..funny, knowing we’ve all had our fair share of “what was I thinking” dates. But for me, the moment you took the guy home and blue balled him out of spite (despite going against every fiber of the bro code), solidifies this story as an instant 10 out of 10. This was the best thing I’ve seen all day, so thank you!!!

    Liked by 1 person

  2. Amy,
    I’m not a big fan of reading. Not in the redneck sort of way, though. It’s just not one of my hobbies, nor is it something I crave during my limited downtime.
    However, I came across your blog today and thought I’d read a couple lines while my computer was busy saving a large file and then move along. Two paragraphs into a random selection and I was hooked. I had to stop and go to the Pilot and read all the way through to here.
    Many of your stories and views on these subjects are completely opposite from mine (apart from being ready to move out of MN), yet your writing style is so human and your expressions are so relatable that I’m drawn in as if these are stories about myself. Reading this was effortless yet eloquent. I don’t know how that’s possible but I think it’s the key and you’ve got it.
    This may not sound like a compliment but that’s what it was meant to be. I hope there will be more to come!

    Liked by 1 person

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