The Dating Chronicles

So… you’re dating again. I’m sorry. Also, congratulations. Also… what are we doing? Because if you’re anything like me, re-entering the world of dating after divorce feels less like “getting back out there” and more like being dropped into the middle of a reality show you didn’t audition for. No script. No rules. Just vibes… and a man named Steve who still uses Hotmail. And here’s the part no one really tells you about dating in your 40s or 50s: The entire world of dating has

The Spark, the Roller Coaster, and the Boundary Queen Era Let’s start with the truth: after a year and a half without a single romantic spark, my body was acting like it was about to file a formal complaint. Not a gentle nudge — I’m talking full “we need to speak to management” energy. I told a friend that even my most loyal gadgets were starting to feel like interns doing their best with limited resources. She nodded with the kind of concern people reserve for small kitchen

Armed with my therapist’s wisdom (and let’s be honest, a slightly delusional amount of optimism), I jumped right back into the upside-down carnival we call online dating. This time, however, I wasn’t going in alone. One of my girls from the tribe, Margot, decided to join me. This is our story. Margot Single mom (one teenage boy) Insurance expert. Introvert. Owner of a backside so impressive it deserves its own postal code. Margot is the kind of woman who reads policy document

The Decision to Pause My dating hiatus lasted one full year. Why? Well, I really meant it when I said I would not date again after Simon — unless I was fully supported by a therapist. The day finally came when my therapist made it to my name on the waiting list. I felt like I had just won the lottery! Therapy and Transformation Mario and I got to work immediately. We dove deep into hunting demons, unpacking baggage, and rebuilding my dating confidence, piece by carefully exam

Simon Age: 47 Occupation: Video game developer Hair: Receding, but deeply committed to the strands still holding the fort. Looks: Cute enough. His Hinge prompts had me laughing so hard I hit “like” before my brain had a chance to intervene. We messaged for about a week, then graduated to actual phone calls. Talking to Simon was like tuning into my own personal comedy show — sharp, witty, timing so good he could’ve charged admission. Before we could meet, he had a business tri

The weather started cooling down. Back-to-school signs popped up on every billboard like giant reminders that my carefree summer fling with freedom was officially over. The emotional trauma of dealing with Santos had subsided (therapy, wine, and selective amnesia helped), but the lessons remained. The tribe came to a consensus: dating sites weren’t the real issue. Nope. The culprit was Facebook Dating—because apparently, it’s where hope goes to die. No quality matches. Just a

So, I broke the ice. Not quite how I’d envisioned it, but still—a start. Or so I thought. After my first date in over two decades, I ghosted Facebook Dating. I was ready to delete the whole app, despite the “council” urging me to “just keep swiping.” That’s when I saw him: Santos. Multiple messages. Persistent energy. I politely replied, saying he seemed nice, but I wasn’t ready to date. He insisted. And… I caved. Naturally, I sent his profile to the council for review. Santo

Disclaimer: Not a psychologist. Just speaking from books, life, and experience. So where was I? Ah yes. The doorbell. I knew it was him. I threw on a robe with the grace of a woman who definitely didn’t regret letting this man into her life. Again. There he was. Puppy eyes. The face of someone who felt mildly bad about being a walking red flag. I sighed, mostly at myself, and let him in. Did my heart melt? No. My heart went, “Oh. It’s you again.” I always knew he was Mister R

I applied the finishing touches to my Facebook Dating profile on a Monday morning and released it into the wild. Then I went about my workday, completely forgetting about it—until lunchtime. As I stood in the kitchen making a sandwich, I decided to peek at my profile. The sheer volume of likes made me gasp equal parts excitement and absolute fear. I’m a relic from the ’90s, for God’s sake. The last time I dated was in 1997. How do you choose a person based solely on a photo a

Let me be clear: the fact that he was dating wasn’t a surprise. He had been doing that while we were still married—so technically, this was more of a formal announcement than breaking news. Still, when he called in the spring of 2022, freshly divorced, to inform me that he had introduced his new girlfriend to our boys… I felt it. Harder than I expected. And because I’m highly skilled at emotional repression (some call it “coping,” I call it “Olympic-level denial”), I took thi

After 22 years of marriage, I didn’t expect to find myself single, over 40, and emotionally supported by a 300-year-old vampire named Dimitri. But here we are. Some women ease into solitude with yoga and green smoothies. I, on the other hand, escaped into books where the men are half-wolf, fully ripped, and declare their undying love in the most unhinged, possessive ways imaginable. It’s toxic, it’s dramatic, and honestly—it’s working for me. Life in the Post-Partner Lane Bei