Wait! You’re ordering for me? And…did you say no tipping?” Welcome to the wild, weird, and wonderfully awkward world of online dating after divorce.
In the final pages of Just Separated: A Hands-on Workbook for Your Separation & Divorce, we dove headfirst into one of the most surprising chapters of post divorce recovery: dating again. And not just the glossy, rom-com kind. We're talking about the real stories, the ones that make you laugh, cringe, and sometimes question reality. The kind of stories that remind you that healing can come with humor, and that the road back to love often includes a few bizarre pit stops.
As we flipped through the insightful pages, the atmosphere shifted to shared experiences and candid discussions about our endeavors in online post-divorce dating. Anecdotes flowed freely, each one a tapestry of craziness and unexpected twists, not limited to our encounters but extending to the stories we had heard over the years from friends and acquaintances.
When Laughter Becomes a Lesson
These were no ordinary tales; they were accounts of shocking and somewhat strange first meetings that sparked laughter among us. Amid the amusement, Kirk's co-author emphatically insisted, "These stories need to find a place in our workbook."
And why not? These narratives weren’t the stuff of fiction; they were genuine, relatable stories that served as more than just sources of entertainment. They stood as tangible reminders that the unexpected is par for the course in the realm of online post-divorce dating. By sharing these stories, we aim to prepare readers for the unpredictability of dating while providing a dose of humor to lighten the journey.
For further insights, check out my previous blog, Spotting Narcissistic Red Flags in Post-Divorce Dating.
Infusing Wisdom with Humor
Including these real life dating experiences in the workbook serves a dual purpose: equipping individuals with practical tools to navigate post-divorce dating and infusing a sense of light-heartedness into what can be a challenging journey.
Dating after divorce is often a mix of unexpected twists and lessons learned. That’s why our workbook includes a section called The Dating Game, a lighthearted yet practical guide to help readers tackle the twists and turns of dating after separation. Here, real-life scenarios meet actionable insights, offering a blend of humor and wisdom.
A Taste of "The Dating Game" Workout: Post-Divorce Dating Tips and Scenarios
If you’re navigating the unpredictable world of post-divorce dating, our workbook has the tools, humor, and insights you need.
Here’s a sneak peek into The Dating Game section of our workbook. Reflect on how you might respond if you were on these dates:
The Silent Toast
(Sitting at a wine bar)
Your date says, “Before we order, would you mind if we have 10 minutes of silence in memory of our failed marriage?”
How would you respond?
The Pre-Planned Meal
(You arrive 5 minutes late to a restaurant on your first date.)
You: “Sorry I’m late, I had trouble finding the place.”
Your date: “No worries. To save time, I ordered for you. You’ll love the octopus and beef tartar—it’s my favorite dish.”
What’s your next move?
The Non-Tipper
(At a restaurant, the waitress brings you the bill.)
Your date: “Throughout school, I worked part-time at a grocery store.”
You: “Waitressing got me through college.”
Your date: “We’re going 50/50, right?”
You: “Oh, okay.”
Your date: “I’m using these coupons for my half, and by the way, I don’t believe in tipping.”
What do you do?
Embracing the Rollercoaster of Post-Divorce Dating
Post-divorce dating is an unpredictable rollercoaster where each encounter is a unique experience. While some may never experience the craziness of these tales, others will undoubtedly have stories to share with friends and family. Amidst the chaos and shock, it’s important to remember that many successful couples have emerged from the world of online dating, even after enduring rough initial dates.
Tips for a Positive Dating Experience
Online dating casts a wide net of potential connections, and finding the right one may take time. Here’s how to make the experience more enjoyable:
Embrace humor: It helps lighten the challenges.
Stay curious: Each person has something to teach you.
Prioritize safety: Meet in public places, share your plans with a friend, and trust your instincts.
Set boundaries: Know your limits and communicate them clearly to protect your emotional well-being.
Focus on connection: Look beyond initial chemistry to find shared values and deeper compatibility.
Take breaks: Pause when needed to recharge and return with a refreshed perspective.
Above all, remember: the best dates aren’t always the ones that go according to plan. Sometimes, it’s the missteps and surprises that make for the best stories, and the most growth. Whether you’re meeting new people or rediscovering yourself, the important thing is to keep moving forward with confidence and a smile.
🎧 Want more guidance? Listen to our Just Separated Podcast episode: Online Dating After Divorce – How to Be Successful, featuring Chapter Two Dating. It’s packed with insights on staying safe, keeping your expectations in check, and having fun while finding the right connection.
Still wondering if you’re in recovery—or just hoping you are?
There’s a point in divorce when the chaos quiets down… but that doesn’t mean the healing is over.
You might feel more clear. More focused. More like yourself again.
But are you really in recovery?
✨ Take our 3-minute quiz: “I’m Ready”
Find out if you’re truly moving into the rebuilding stage—or if you’re still stuck in a pattern that’s holding you back.
🔎 This quiz helps you get honest about where you are so you can take the next step—confidently.
