Dating Red Flags: Being Asked Out Via MSN

Originally posted on

After my first ‘relationship,’ if it can even be called that, you would have thought I knew better. Yesterday, I posted a poem I wrote in 2004 where I realized I could not shoulder the world’s burdens. That girl must have taken a time out in 2006. My 16-year-old self relapsed into thinking she could carry the weight of the world on her shoulders. It was that way of thinking that would lead me through three months of red flags.

This is just too much for one blog post. I’m calling this the *Zachery Saga.


High school is fulled of crazed children with even crazier hormones. I didn’t care for any of the drama I saw so many people get involved in, but I was always willing to offer my opinion if it was requested, especially for my best friend. She was in a bind between two brothers, one a year older than us and one a year younger. They both expressed interest in dating her and she was trying to make a choice.

These brothers were like night and day. The younger was a lively goofball with an annoying habit of pushing people’s button. The older was introverted and quiet. He hung around our group of friends, but rarely engaged. To an onlooker, it would have seemed like he was eavesdropping on us because he never really stood with our group either.

She choose the younger brother.

Some awkwardness followed because the older brother, the one and only Zachery, felt like my friend had been stolen from him. Eventually, things seemed to settle into a normal rhythm. That would be my mistake.

Not longer after my friend’s relationship began, I was talking with her over MSN. It was late and we were both getting ready for bed. The moment my friend logged off the instant messaging service, I had a message from Zachery.

He asked, via MSN, if I was interested in dating him. In hindsight, that was a big red flag. He couldn’t even ask for my phone number is use his voice to ask me out? It didn’t matter, because I didn’t really have the self-esteem to say no.

I wish my friend hadn’t logged off. All I wanted to do in that moment was ask for her opinion. He probably asked me out at that moment because I couldn’t lean on my friend for support. I was alone in this internet space, without a trusted companion from whom I could seek counsel. I accepted his offer after noting that I wanted to take things slowly.

 My relationship with Zachery would spiral real fast. He was both clingy and quick to anger. More than once during our relationship, I would fear for my well-being or the well-being of those around me.

I think about this moment, when he chose a computer as his method of asking me out, as a sign of bad things to come. He picked that method because it was easy and I would soon learn he took the easy way out when possible. He’d even speed up his car so he didn’t have to be bothered pressing his foot to the pedal for too long.

I still wonder if he picked me for that same reason. Did he think I was easy? Maybe he was just looking for an excuse to get close to my friend, even though she was dating his brother.

What is the worst way you’ve ever been asked out? Did you accept? Looking back, what sort of red flags do you see in your failed relationships? Would you ever date a family member of your friend’s significant other?

Stay tuned for next week, when Zachery drops a four letter word and I realize just what I’ve signed up for.

*Zachery isn’t this guy’s real name.

Twitter: @tkrv12


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