Chapter 44: I Deleted My Dating Apps ft. The Baseball Player and The Namecaller

July 21, 2021.Reading time 20 minutes.

Y’all, I just couldn’t do it anymore – I deleted my dating apps. A few weeks ago, I deleted Tinder and Bumble. But, I did make a Hinge profile specifically so that I can get an idea of what the options are like when I was in Austin and Scottsdale (more on that later). But […]

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CHAPTER 43: THE CHEF, PART II

June 29, 2021.Reading time 23 minutes.

In my last post, I told you that part two of my story with The Chef, Francisco, might be coming. And, guess what? It did. After he randomly reappeared in my life several weeks after our first date, I decided to give him one more chance. As I said, he wasn’t completely awful on our […]

Chapter 42: One Hit Blunders, Part VII

June 22, 2021.Reading time 20 minutes.

If you had asked me a few months ago if I thought I’d end up with this many One Hit Blunders chapters, I’d have said no. But, here we are. The weather has been getting nicer and people are getting vaccinated. So that means that I’ve been more actively pursuing dates with some of my […]

Chapter 41: The Reality show model

May 4, 2021.Reading time 11 minutes.

Every once in a while, I realize that I have been holding onto what could be a great story. Sometimes I completely forget to ever write about them until something randomly reminds me, and for that, I apologize. This is one of those cases. And, it’s all thanks to a TikTok video and a comment […]

Chapter 40: Grocery store guy

April 6, 2021.Reading time 16 minutes.

Growing up as a child of the 90s, plus a Disney lover, I’ve seen about every single movie “meet-cute” you can think of. The dog leashes getting twisted at the park, getting in the same taxi, you name it, I’ve probably seen it. But one that always sort of stood out to me as especially cute was the grocery store meetup.

Chapter 39: The Disappearing Act

March 9, 2021.Reading time 18 minutes.

Hello, friends! Sorry for the unexpected hiatus. I had another shortage of material and then a crazy week so I’m a bit behind.
Speaking of unexpected disappearances, that brings me to this week’s post. Let me introduce you to Mac, yet another Bumble-bust.

Chapter 38: The Actor

February 16, 2021.Reading time 17 minutes.

Don’t judge me, but back in the day, I was VERY into “Teen Wolf.” And by ‘back in the day,’ I mean five years ago. I’d like to say that I was mostly interested in it because Tyler Hoechlin is a beautiful man, which is true. Or, because I fell for Dylan O’Brien’s comedic timing, […]

Chapter 37: One Hit Blunders, Part VI – The Russian

February 9, 2021.Reading time 14 minutes.

When I got back to Boston after the holidays, I was eager to get back into the dating world. Like I said in my Q&A last week, lately I’ve been doing a lot of work on myself. After taking lots of “me-time,” I finally feel ready for a real relationship. I just need to meet […]

Chapter 36: Questions & Answers

February 2, 2021.Reading time 23 minutes.

Hello again, friends! Welcome back to another week. It feels so good to be writing again, and I’m especially excited for this week’s chapter. A little while ago, I asked my friends on Instagram to ask me some dating and sex-related questions that I could answer on my blog, and they delivered. So while I […]

Chapter 35: The Stage-Five-Clinger

January 26, 2021.Reading time 11 minutes.

It’s been a minute (or lots of minutes), but I’m back at it! Welcome back to Confessions of a Singleholic, ladies and gentlemen. Today I have a fun little story for you about my favorite type of person. A guy I’ve never even met getting clingy and needy. This story is brought to you by […]

Madeline Olsen

Category: Confessions of a Singleholic