Mr. Insecure

After attending a social group recently, I was asked out by one of the members. He was attractive and funny, so I accepted. He texted me multiple times before our non-date (he told me if this casual meeting over drinks and food went well that he’d ask me out on a real date) and I got a weird vibe from the texts, but he had mentioned he hated texting because of the lack of context, so I chalked it up to an impersonal method of communication.

The non-date began fairly well. He’s new to the city, so I chose a tapas restaurant that never disappoints and is a local treasure. We talked about movies and music and food, all fairly casual subjects. I was unpleasantly surprised when he chose to mockingly impersonate a person who was sitting fairly close to us, yet thought I’d see how the rest of the evening went. As the night progressed, the pattern I began to see was of a man who was deeply insecure. He verbally assessed my body language to try to gauge my interest in him. He continued to comprise little tests, to try to figure out if I had a hidden agenda or was just being nice. He mentioned his interest in me several times, then anxiously said, “See? Now you have all the power.” He tried to cross several boundaries that I was uncomfortable with.

And in my head, I kept envisioning the new social group that I’d just joined and how awkward it would be to run into him there…because I sensed it was all going downhill.

He asked me out again and like a coward, I said yes. But driving home, I knew that I couldn’t possibly keep the date. I kept praying I’d be given a really good reason to cancel that would let him down easy and not create a big scene.

Be careful what you pray for.


In the week since the date he has texted me close to 100 times. He has sent pictures of himself, repeatedly, with the captions going something like this:

“This is the tie I’m wearing today.”

“This is what I look like today.”

“What do you think about this look?”

He was clingy and needy and ridiculously over-the-top and I felt increasingly annoyed. Until finally, he asked the question that started it all.

“Is it okay if I ask you a very forward question?”

Uhm…no. Not even slightly okay. I used the chance to set some boundaries straight and let him know I hadn’t appreciated some of his behavior the week before. He launches into a full-blown text panic attack, completely overcompensating and going on and on about how he didn’t mean it, he would fix it, he’d be better…but always ending with something along the lines of “But I can tell you don’t like me now.”

Finally, he tells me how much he misses me. To which I reply: “How? You’ve met me twice!”

Another long, novel-length text about his attraction to me, his interest, his willingness to prove his interest…”But I can tell by your answers that you’re disinterested.”

Finally, even my non-confrontational, passiveness about the situation had reached a breaking point. I canceled our plans (which I didn’t want to keep anyway) and told him I couldn’t deal with the drama and insecurity after ONE date.

Lengthy, pleading texts ensued.


He seemed normal when we met at the social group. Now I suppose I’ll get to circle the room at the next event and pray he stays far, far away from me. I prayed for a reason to cancel the plans that left him with dignity and me with a gentle exit strategy. Talk about a half-answered prayer! I got my reason, but now I have no doubt he is completely humiliated and I hope to never see him again…which isn’t great…considering the social group.

Double sigh.

How does one go from seeming normal to full-blown crazy within two weeks?

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