EX Files: The Date That Wasn’t

Investment Piece: Ex Files: Valentine's

It’s ex-files, where we stop chatting fashion for just a minute and talk dating horror stories. An attempt to be like Carrie Bradshaw? Sure. But let’s be honest, dating horror stories are both horrifying and funny. Names may have been changed to protect identities, some details moved about. Hungry for more? Try: Tinder on an Airplane, Jumping to Conclusions, and The One Who Asked for his Money Back. There are quite a few more when you search “ex files” in the search tab!” Also if you want to be written warmly about- behave better! xo RA

This month’s ex files may take liberty with the word ex- as it’s not like we are exes. BUT. Let’s admit that dating is supposed to be the process of seeing who might be compatible with you for a long term relationship. Or at least at short term meet up. So when the person you’re supposed to me (or are writing about!) throw red flags as if they were confetti what do you do- other than not go??

And to be fair? This dude may not know that he was giving off red flags. And in my 20s I would have politely bit my lip, met up and hated him. Now that I’m not 22– I just said no. Here’s what happened:

Ryan and I met in an alumni club. What may be my fault: he is in real estate. My sister and I do notary on the side so when he messaged me in an alumni local group I assumed that was what he wanted to meet up about. He never mentioned drinks or dinner- it was always “meet up”. SO – I would give our availability and leave it. This went on for months.

Then. Messages got to the point where I got that he was asking me out (aka all of the sudden he mentioned he was interested in meeting me and wanted to get to know me)– and yet when I let Ryan know when I was free he was either busy or didn’t respond. After checking him out (yes- the internet works both ways thankfully!) I was pretty determined Ryan and I weren’t a match.

Then. He messaged me letting me know he was desperate to meet me. HE would do anything. I gave him some times. We made a plan. He canceled last min. As I was raised to be over accommodating I let him know that I was fee for coffee all the next morning. He texted me at 4p that day asking what my day looked like. I let him know that at this point I was in, I had given him times and hadn’t heard from him, had an early morning the next day and that it wasn’t good timing for me.

Ryan responded by throwing a fit over text. Letting me know that he wanted to me. That he didn’t understand the time frame. That he was going out (although in a different city) and I should meet up. Whining when I said no. Whining more when I mentioned that was not where I lived (think- Manhattan to Brooklyn), and whining MORE when I said I had a bed time as I had an early call time. Essentially crying and pushing back at all my boundaries.

And in my 20s- I probably would have relented. I would have said yes. And met him and have secretly been mad. Or when Ryan suggested a drink after my early call time I would have said yes and made sure I made it. Great news for me? I’m not in my 20s!! I no longer care about what random Ryan’s think- because truly- if they wanted to they would make a plan. Ask you out. Take all your notes into the plan.

Whining at me. Blaming me for “not meeting sooner”, acting like a 5 yo when someone said the slightest no? Not something I want in a partner. And perhaps the difference in my dating now is that I’m not looking for a date- I am super happy at home with my closet. To get past that, I need a partner. And if you let me know from the get go you’ll be a horrid one- why would I get past “hi”?

AKA. The older I am the less I let red flags fly. What are some of yours? What was a sign that someone was not for you?


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Actress, avid shopper, and a lover of fashion. Hoping to make the world a better place one pair of shoes at a time.