Older, Rich, Sexy… and Emotionally Unavailable as Hell
- CJM

- Sep 8, 2025
- 4 min read
Picture this…you’ve survived speed dating, and then days later you meet this blonde, sexy, affluent man in a bar. You and your bestie spend hours talking to him over martinis. He offers to drive you home after you share a kiss, and it feels like fireworks.
Before we go any further...you can relax, I’m not totally going to roast him—he never asked enough about me to know that a blog could exist!
Two weeks ago, this was my Friday night, and I woke up the next morning insanely excited for what it might turn into. I immediately started building him up in my head (don’t you love being a girl?) and my anxious attachment gremlin inside was screaming at me that "HE'S THE ONE". This gremlin inspired me to text him to plan a date early in the week.
In classic Charlotte fashion, everyone in my life knew about this sexy man and our upcoming date. It was a spontaneous date wherein my hair was not washed, but we powered through!
He met me at a bar in Allston for dinner and arrived late, (I had already ordered Grey Goose on his tab) expressing how frazzled, stressed, and busy he was. Uhmmm…sorry? I immediately felt guilty. For what exactly?
90 minutes turned into a free therapy session about his foot surgery and family issues while he drank tequila on the rocks. My gut was firing off alerts to me of him being a massive red flag. It was hard to get a word in edgewise, and I found myself saying “Oh god” in my head the entire time. Not to mention we didn’t even order food! Liquid dinners for everyone.
He brought up how he skis, his 3 vacation homes, and how he loves to travel. He offered to come to all my upcoming weddings on his private jet. Hmm…can I make this work anyways? My anxious attachment monster was trying to make excuses for his behavior and minimize the red flags. Misogynistic? It’s fine, sounds like he’s had negative relationship experiences! Claiming he isn’t an alcoholic? Hmm…well maybe 2-4 drinks daily is fine!
Lord have mercy. He tried to invite himself over to 'rest his ankle' on a couch, but I politely declined. He eventually dropped me off—not without telling me how constipated his pain pills make him—and I went home to call everyone reporting back that it was a ‘great date.’ I framed it as he was very busy with family issues and his own health…but he’s a great guy.
I don’t know why I framed it in a less toxic light. I guess I felt ashamed it turned out like this and not better. It was a mix of my anticipation, and my anxious attachment gremlin wanted to frame it as ‘good’ in hopes that it eventually turned out that way. I didn't want to share another failed first date story. And how was I supposed to weave in that he trauma dumped (no pun intended) about his constipation?!
From fireworks to foot-pain-and-tequila reality, my heart and my anxious attachment were at war.
In true self-centered fashion, he only texted when I reached out. But the weekend after, while I was at a family wedding in Florida, he called me no less than five times—even though I only answered one. It felt like boundary testing and slightly obsessive. But how nice was it to be wanted.
When I flew home, he wanted to see me that night, even though I was exhausted. I asked about the plan three hours before he said he'd pick me up, only to have him cancel- blaming it on ‘personal issues’—proof that his availability always operates on his own terms.
Did I ever hear from him again?
Not until a few days ago, while I was in NYC, did he call. He was drunk at a bar—and told me he was going to sleep with a girl he just met. Total power move to test my reaction.
Because nothing says ‘emotionally unavailable’ like calling to brag about a bar hookup. I mean really...do I need that update? Hey Alexa! Play Nobody's Son by Sabrina on repeat!
Logically I know that if I reach out, he will answer, but what's the point? Why do I want a disrespectful man who only operates from his own terms? He’s so wounded he can’t show up for anyone—and as much as it makes me sad, he’s not mine to fix.
In the days after we cancelled our date and he was MIA; my anxious attachment monster was firing off in all directions. A constant push and pull of “should I just text him?” on repeat in my head. He promised all those amazing plans to me...and he is a regular at that expensive steakhouse that I've dreamed about going to!
16-year-old me was begging for these breadcrumbs of love, while 28-year-old mostly healed me, was saying “No thank you! We don’t need to be reaching out to a man who uses us for his own validation.”
This is a hard position for someone like me who craves romantic validation and attention above all else. It consists of a lot of reframing, alternating my thoughts around ‘unworthiness’ and ‘not enough’, to him not being able to provide what I need. And that is okay.
Closure comes from a man’s actions. Not their words. And how do I expect a partner to love me when I haven’t healed all parts of me yet? I'm proud of me for knowing I deserve more.
We trek onward ever forward…wiser, mostly healed, and still a baddie.
Love,
Uncle C
PS- Remember I’m not completely trashing him here…mostly because he’s blissfully unaware I have a blog where I could! Thanks for never asking more about me babe!


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