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The Dating App Disaster: Jordan's Journey
- Shade Goddess
- 5 days ago
- 6 min read
The Dating App Disaster
A 38-year-old divorced dad learns the hard way that you can’t skip the healing to get to the happy ending.
Jordan stared at his phone screen, thumb hovering over the download button. Hinge. Bumble. Tinder. The holy trinity of modern dating, according to his buddy Marcus, who’d been divorced for three years and seemed to have it all figured out.
“Bro, you’ve been single for a year and a half,” Marcus had said over beers last weekend. “Michelle’s already moved on. What are you waiting for?”
What was he waiting for?
Jordan didn’t have an answer. So here he was, Saturday night, kids at their mom’s house, downloading his first dating app in 15 years. How hard could it be?
The Profile That Screamed “I’m Not Ready”
Jordan scrolled through his camera roll looking for photos. Most were of Emma and Tyler. A few work headshots. Then he found it—a picture from his buddy’s wedding two years ago. He looked good. Confident. Happy. Never mind that he was still married then.
Bio time. Jordan typed:
“Love to laugh and have a good time. Enjoy sports, traveling, and spending time with my kids. Looking for someone genuine. Great dad. Hard worker. Let’s grab coffee!”
He hit publish and felt a small surge of pride. He was back in the game.
Within an hour, he had three matches. By Sunday morning, he had a date lined up for Tuesday.
This was going to be easier than he thought.
The Coffee Date From Hell
Her name was Jessica. 34, marketing consultant, loved hiking and trying new restaurants. They agreed to meet at a coffee shop near downtown.
Jordan arrived ten minutes early, palms sweating. When was the last time he’d been on a first date? College? He couldn’t remember.
Jessica walked in—pretty, warm smile, exactly like her photos. They ordered drinks and sat down.
“So,” she said, stirring her latte, “tell me about yourself.”
And that’s when everything went sideways.
“Well, I’m divorced,” Jordan started. “It’s been about 18 months. We were together for 12 years. She’s a great person, we just… grew apart, you know? She felt like I worked too much, but I was just trying to provide for the family. I mean, someone has to pay the bills, right?”
Jessica nodded politely.
Jordan kept going.
“The hardest part is the kids. I have them every other week, and it’s just… different. Michelle—that’s my ex—she’s already dating someone. Can you believe that? I mean, good for her, I guess, but it’s only been 18 months. Seems fast to me…”
Forty-five minutes later, Jordan was still talking about his marriage, the divorce mediation, how his ex loaded the dishwasher wrong, and how he missed his old house.
Jessica glanced at her phone. “Oh wow, I didn’t realize the time. I actually have a… thing I need to get to.”
“Already?” Jordan checked his watch. They’d only been there an hour.
“Yeah, sorry. It was really nice meeting you, Jordan.” She stood, grabbed her purse, and was out the door before he could offer to walk her to her car.
The Rearview Mirror Moment
Jordan sat in his car in the parking lot, replaying the date in his head. What just happened?
He pulled out his phone and opened the dating app. No new messages. He refreshed. Nothing.
Then he looked up and caught his reflection in the rearview mirror.
“Who am I now?”
The question hit him like a punch to the gut.
For 12 years, he’d been a husband. A provider. Part of a unit. Now he was… what? A divorced dad? A weekend father? A guy who couldn’t make it through a coffee date without trauma-dumping on a stranger?
He wasn’t ready for this. Not even close.
Jordan deleted the app.
The Lessons: What Jordan (and You) Need to Know
1. Healing Must Come Before Dating
Jordan’s biggest mistake wasn’t his outdated photos or generic bio—it was thinking he could skip the grief and jump straight into connection. You can’t build a healthy relationship on an unhealed foundation.
If you’re still processing your past relationship, still angry, still talking about your ex on first dates—you’re not ready. And that’s okay.
2. Your Dating Profile Reflects Your Self-Awareness
“Love to laugh. Great dad. Hard worker.”
Who doesn’t love to laugh? Jordan’s profile was generic because he didn’t know who he was anymore outside of his old roles. Your dating profile should reflect your authentic self—your interests, values, what makes you unique.
Ask yourself: If someone read my profile, would they know what makes me different from every other person on the app?
3. It’s Okay to Not Be Ready
There’s pressure to “get back out there” after a breakup or divorce. Friends mean well, but only you know when you’re ready. Taking time to heal isn’t weakness—it’s wisdom.
Jordan needed to rediscover himself before he could share himself with someone new.
Expert Commentary: Nyomi’s Take
Let’s keep it real—Jordan’s date was a disaster, but it was also a gift.
Here’s what I see happening: Jordan is carrying unprocessed pain, unresolved identity questions, and unhealed wounds into the dating world. He’s looking for external validation to fill an internal void. That never works.
How to Know If You’re Ready to Date After Divorce
Ask yourself these questions:
1. Can I talk about my past relationship without bitterness or excessive emotion?
If you’re still angry, still defending yourself, or still processing—you’re not ready. You should be able to discuss your past calmly, with perspective and ownership of your part.
2. Do I know who I am outside of my past relationship?
Jordan lost himself in his role as husband and provider. Who are you now? What do you enjoy? What are your values? What do you want in life?
3. Am I looking for a partner or a distraction?
Be honest. Are you dating because you’re lonely? Bored? Trying to prove something? Or are you genuinely ready to build something new with someone?
4. Have I done the inner work?
Therapy. Journaling. Self-reflection. Processing your emotions. Healing isn’t passive—it’s active work. Have you done it?
Creating an Authentic Dating Profile
Your profile should answer three questions:
· Who am I? (Beyond your job and parental status)
· What do I value? (What matters to you in life and relationships)
· What am I looking for? (Be specific about what you want)
Example:
“Recently rediscovered my love for cooking after years of takeout. Sunday mornings are for pancakes with my kids and terrible dad jokes. I value honesty, growth, and deep conversations over surface-level small talk. Looking for someone who’s done their healing work and ready to build something real.”
See the difference? Specific. Authentic. Self-aware.
The Importance of Doing Your Inner Work First
Dating before you’re healed is like building a house on sand. It might look good for a while, but eventually, it will crumble.
Inner work includes:
· Processing your emotions about your past relationship
· Identifying patterns that led to the breakup
· Rebuilding your sense of self
· Healing your attachment wounds
· Learning healthy relationship skills
This isn’t optional. If you skip this step, you’ll repeat the same patterns with different people.
Reflection Questions
Take a moment to honestly answer these:
1. Am I dating because I’m ready, or because I feel like I should be?
2. What unresolved emotions am I still carrying from my past relationship?
3. Who am I now, outside of my past roles and relationships?
4. What inner work do I need to do before I’m truly ready to date?
What’s Next for Jordan?
Jordan deleted the dating apps, but his journey is just beginning. In Episode 3: “The Co-Parenting Conflict,” Jordan faces a new challenge when his ex-wife introduces her new boyfriend—and Jordan has to confront feelings he didn’t know he still had.
Will Jordan learn to set healthy boundaries? Can he process his jealousy without becoming the bitter ex? And what does healthy co-parenting really look like?
Find out in two weeks.
Join the Conversation
Have you ever gone on a date before you were ready? What happened? Share your story in the comments below—your experience might help someone else on their journey.
And if Jordan’s story resonates with you, subscribe to our newsletter to get notified when the next episode drops, plus exclusive resources for men navigating love after divorce.
Remember: Healing isn’t linear, and there’s no timeline for when you “should” be ready. Take your time. Do the work. Your future self—and your future partner—will thank you.
Always Keep It So Sexy,
Nyomi
Related Resources:
· Download: Co-Parenting Communication Guide
· Read: “5 Signs You’re Not Ready to Date (And That’s Okay)”
· Shop: Self-Worth Workbook for Men
Tags: #AskHim #JordansJourney #DatingAfterDivorce #MenAndRelationships #HealingJourney #DivorcedDad #RelationshipAdvice #SelfLove #PersonalGrowth
This is a fictional character story created for educational and entertainment purposes. Jordan’s journey is designed to help real men navigate similar challenges in their own lives.
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