Ex Files: The High School “Friend”

Marlin Monroe accepts a drink from a man while sitting next to Sammy Davis Jr. Text: I love You. Thanks

In my attempt to not only be Carrie Bradshaw, but entertain us all with the horror stories that can make up single life it’s Ex Files! Every month you get a look at some (real) bad dates that I have endured, and lived to tell the tale. Names and some facts have been changed to protect people, but I own the stories!

Need more horror in your life? Check out: The One Who Wanted His Money Back, The One Who Got Married, The One Who Wouldn’t Take No, The One Who Commented on my Weight. And if you aren’t scared stiff, the search tab has even more stories for your dating horror pleasure.

This month we have : The High School “Friend”

Because sometimes dating horror stories come from those you never even dated, like your high school “friends”. Jon and I knew each other in high school, we had friend circles and activities that overlapped, we went to the same church, our moms were friends. But I never would have considered him a friend. He wasn’t NOT a friend, and wasn’t an enemy, but I (for the life of me) can’t recall any one on one time or conversation with Jon. We were friendly. And I didn’t hate him. But to this day I can only remember the bare minimum about Jon (and most of that is because of Facebook and my mom).

Again, it’s not that we weren’t friends, but Jon and I were never close or personal friends; it was more that Jon was in circles I sometimes ran with.

So, as it goes, Jon and I graduated from high school and went off to college. (Fun fact, I can’t even remember where he went!). We would see each other over the years when each of us come back home, on summers home from college and vacation as we became adults with jobs. (Again, I think Jon works in Tech but I am not sure!). As we got older what began to creep me out about Jon were the comments he would make to me about my body.

I wasn’t fat in high school, but I was much more chubby than I am now and didn’t have a lot of confidence. I always had a sense of style, but college and being out in LA really let me grow into myself (I’m sure I’m not the only one with some issues from high school and a less than Disney experience). As I found workouts and diets, style and confidence that really let me shine, Jon would always compliment me. Which is nice. But we all know that compliments are one thing and a guy leering at you and saying “WOW. You look SO Good” and almost licking his lips are two different things. (In a moment of petty, let me say the years haven’t been as kind to Jon, and while he would love to tell you how much smarter he is than you are, Jon is not my type. At all. In a kindness way especially.) Understandably, Jon became someone I never sought out while I was home.

Which worked out! Jon married someone he met on an internship, they have 3 kids, and from Facebook look suburban happy! For the past few years, I haven’t really interacted with Jon at all, even on Social Media.

So, imagine my surprise when I got a DM from Jon recently. When I first saw his name I assumed it would be about the “unofficial” class reunion he was helping to plan. I was mistaken. Jon was messaging me to let me know that he had planned to go to a concert in my town and was expecting to sleep on my couch. Yes, that’s right, someone I had never been close to or spoken with in years was thinking that I (in his words) “owed” him a place to stay for a concert and he was “looking forward to catching up”. For many reasons, including that my couch is unavailable, I let him know that I wouldn’t be able to host him and that he was on his own for a room to stay in at the out of town concert he had planned for himself.

Surprisingly to no one, once I let Jon know that I couldn’t accommodate him, he got very angry. Jon let me know that he always liked me (yes, he’s still married), and that I should be a better friend to him after all we’ve been through (I think these Dms are our first real one on one convo). Even my mom, who I related the whole thing to, was appalled by Jon’s behavior. In my mom’s words: “Why would a married man assume that an attractive single woman he has no connection to would go out of her way to let him stay alone at her apartment?” Good question Mom. In fact, regardless of Jon’s intentions, I was incredibly creeped out by his behavior. I stopped responding to his messages, once he let me know how mad we was at me. Did he get a place to stay? Sounds like a Jon problem to me!

Have you ever had a casual acquaintance all of the sudden think that you owe them? Isn’t it the worst!?


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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.

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