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He Asked For Nudes Before We Even Kissed And 5 Other Red Flags I Missed As A Dating Writer

3 0
09.08.2025

We met on Bumble.

He was a tall, handsome military doctor who used full sentences, proper punctuation and asked thoughtful questions about my writing and my life. It felt like grown-up dating was finally delivering on its promise: warm, curious and full of Oxford commas. I thought I’d found a good one.

I was wrong.

Here’s the thing about dating in your 40s and being a dating and relationships writer: you think you’ve learned something. You’ve read the books and been to therapy. You think you know what to look for. You know what an avoidant attachment style looks and sounds like. You know what “I’m too busy” really means. You know if “he wanted to, he would” is usually a legit litmus test for a man’s investment in you.

What defines a “red flag” for you may be different than the person you’re getting to know. It helps to know yourself and what you really want.

But then a hot Navy doctor slides into your life with good spelling and a defined jawline, and you forget everything.

Not because I’m an idiot who hasn’t learned anything, but because I’m human. I’m a single woman with a big heart and an unruly black cat, swiping on guys, asking one of them to love me (when warranted and vetted, of course).

When Hot Navy Doctor bounced (although I think “hot” is pushing it a little, but it has a better ring to it than “Above Average Attractive” Navy Doctor), I was disappointed, but I wasn’t surprised.

In retrospect, there had been a ton of red flags waving in my face like I was at a NASCAR race. As someone who’s been writing about dating and relationships for over 10 years, I couldn’t believe that I missed some of the most obvious ones. Maybe “missed” is the wrong word ― it was more like I “ignored” them or made excuses for them ― the very same excuses that I’ve written about not making in my professional life.

Here are the red flags I missed ― and ones that I would advise not ignoring or making excuses for, and, instead, letting their blatant disrespect or disinterest be enough for you to cut your losses and move on a heck of a lot quicker than I did.

He was busy — a lot.

He was a doctor and in the military. There were deployments, late nights and long shifts. This meant he was texting less and planning fewer dates, and sometimes going long stretches without contacting me. Near the end of our “situationship,” he didn’t contact me for a month. I chalked it up to him being on a Navy ship in the middle of the ocean.

But here’s the thing: If our connection had mattered to him, he would’ve shown up. He would’ve responded to a simple text, “Let me know how you’re doing when you can!” But he didn’t.

We didn’t talk about what we were looking for in terms of dating.

Which brings me to my next point. I think if our connection were something he was serious about (or at least, half-way interested in), he would’ve made more attempts at communicating and being clear about, well, everything. But we never discussed what we wanted in terms of dating. We didn’t ask each other, “Why are you on this app? What are you........

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