I’m Dating a Grandmother?

R. James Miller
6 min readJul 9, 2020

The Crazy eX-Files: Part 1

Photo by Alex Harvey 🤙🏻 on Unsplash

“Are you seriously dating my sister?”

“Yes, she seems like a great girl. BTW nice to ‘meet’ you.”

“Did she tell you she is about to be a grandmother?”

She did not, in fact, tell me she was about to be a grandmother. To be more specific, she did not tell me she had a 20-year-old daughter. I knew about the 9, 11, and 18-year-old sons. However, at no point during our first month of dating did she inform me of the daughter who was about to make her a grandmother.

This was my introduction to exactly how deceitful the woman I would eventually fall in love with could be. It was also the first day we had officially become a couple. It was also the moment I really began to ignore serious red flags.

I was having this revealing text conversation with her sister via Facebook Messenger as I was walking home from a bar where she had gone to meet the guy she was dating before me. Yes, I know that sentence is confusing so let me give a little background on our first day as a couple.

I had asked her if she wanted to make things exclusive the night before. We drank and sang karaoke all night to celebrate. We made things “Facebook official” the next morning while we lay in bed.

--

--

R. James Miller

Mental health, emotional wellness, opinion, & travel-focused writer. Writing about my weight struggles, personal growth, and wanderlust.