When your therapist asks you if you’ve ever thought about doing something to potentially monetize off of your dating life, you know it’s crazy.

For those of you who don’t know me, my name is Madeline. I’m 28, from North Carolina, just finished grad school in Boston, unemployed because of Covid-19, and single. I’m a Sagittarius (and yes, that is important), an Enneagram Type 8, and an ENFP (formerly ENFJ). I have an amazing older brother and incredible parents, my best friend lives in Australia, and I quote movies like it’s my job.

If I’m being perfectly honest, which I always am (part of being a Sagittarius), I could go on about myself for ages. So, to make this a bit easier, and a lot easier to digest, here are some things you need to know about me before starting to read this:

  • I was a late bloomer. My first kiss was in a play – The Crucible – when I was 17. I didn’t technically kiss anyone else until I was 21, and I didn’t even go on a date until my Sophomore year of college. And let’s just say (for now, at least) that everything else was pretty delayed, too 
  • My friends call me the Queen of It’s Complicated relationships, because I somehow manage to always be in that weird middle-ground between friends-with-benefits and actual boyfriend/girlfriend (who needs labels anyway, right?).
  • Going back to my first point – growing up, I struggled with my weight a lot, and I had extremely low self-esteem. I never felt pretty or hot, and felt like I’d always just be “The Cute One” or “The Smart One” to guys I liked, because I was never the one they wanted to date. That messed with me a lot until I was in my 20s.

While some of that might seem sad, and at times, it was, now that I’m grown up, I realize that as cheesy as it sounds, all of that has made me who I am. I’ve still had some amazing experiences, and I like who I’ve become because of the fact that I did a lot of things a lot later than my friends. Even better, I think because of my delayed entry into the dating world, it’s somehow given me SO many more hilarious, crazy stories to share.

So, that’s me. Here I am. While most of these blog “chapters” will revolve around one specific guy in my life, there are times where some might overlap, and yes, you’ll learn a bit more about me along the way, too. 

As my friends already know, I tend to give every guy who has played some sort of role in my life a nickname that I use more than their actual name. I’ll tell a story and say, “The Narcissist and I went to eat pancakes,” or, “The Cheater never understood my pop culture references,” etc. It’s nothing against them, (just kidding, it is, for most of them at least) but I’ve just always found it easier and honestly, much more entertaining this way. So, each chapter will be titled after the nickname my friends and I dubbed upon that specific guy who will be the subject of that entry.

If you don’t enjoy reading about a 20-something year old girl and the sometimes mildly terrifying experiences she’s had navigating dating apps and IRL dating, then this isn’t for you. But if you find dating horror stories humorous, and want to know the best way to subtly get back at the guy who cheated on his girlfriend with you, or hear more about the time I got sent a Snapchat of a 9” dildo at 6AM, then, this blog is for you.

Hope you enjoy.

PS: All first names have been changed to protect the individual’s identity and privacy. 

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