Why does he like my friend and not me? Episode 1

As written in Episode 3 (but yes, the first installment), it’s inevitable that there will be men who reach out to my friend Katharine and me at the same time. Or who like one of us and not the other. So far, these few incidents have always been in her favour, but I’ve gotten laid a lot more. So I guess success depends on your measurement.

The first occurrence of this was just weird. It was late November, and Katharine had been telling me about this guy named Dave who had reached out to her online and they connected due to his intelligence, wit, and interest in her. He was obviously a high-powered executive and that’s something she is looking for. They moved to texting. She told me that he was highly annoying on text because if she didn’t respond right away, he would send messages like “zzzzzzzzzzzzzzzzzzzzz” to get her attention. He ended up saying something bitchy to her and she stopped reaching out.

This story, sadly, wasn’t memorable because it was so similar to the other stupid shit with dudes we were going through at the time.

Fast forward a couple of weeks. I’m looking at my “who is interested in you” list on the same site, and I see a photo of a guy who looks really familiar. He looks familiar because, although he’s wearing sunglasses, I swear it’s my old boss from a decade ago. Now, this is weird for several reasons:

  1. Alright, obvious one is that he was MY BOSS.
  2. While some of you may argue that the workplace is a great place to meet lovers (and yes, I’ve proven this to be the case), this man never showed any interest in me whatsoever.
  3. He was exceedingly impersonal. We never talked about anything but work, when we went on business trips together there was never an after-work hangout with drinks, nothing.
  4. Ever since we stopped working together 10 years ago, we would meet for lunch once a year or so. Once we got stuck at a crazy table that only had a small loveseat and it was the most uncomfortable thing ever because he seemed to not be able to get far away enough from me.
  5. My photos really look like me. So it’s not really possible he thought I was someone else, was it?

This kind of freaks me out. But I’m curious at the same time. I find myself saying stupid shit like “maybe he was always attracted to me and that’s why he never seemed to be?” Eventually I just decided to respond. So without using his name, I reached out to him and asked something vague. He responded back, was a bit flirty, and didn’t use my name. This was strange. I was puzzled.

On Christmas night, Katharine and her two children came over for dinner (along with my parents, my step-parents, half-brother, my ex husband – all good times!). I told her I was weirded out because my ex-boss reached out…and then showed her his profile…and he said “oh my god, that’s that jerk Dave”.

No. Fucking. Way.

So then I knew for sure it was him and decided to have a little fun. I sent him the following note (paraphrasing of course since I can no longer access it):

Hi Dave,

I’m curious whether you’ve subsequently had an “oh shit” moment or if you always knew it was me. I am [blah blah about being split from my ex, a bit about my job, etc]. It’s been a while since we’ve caught up about work so if you would like to meet for lunch or a drink after work, let me know.

His response?

Hi Ann. Sure.

Needless to say, with that resounding show of interest, I didn’t pursue it. But now if I actually need to talk to him about work…how the fuck do I reach out now?

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