Second Act Dating: My Boyfriend Wouldn’t Sleep With Me

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My fellow single BFF, Cici Rhoads, blurted out the following, “My new boyfriend wouldn’t sleep with me. Instead I slept in a twin-size bed, alone!”  I chuckled so loudly my neighbor could hear me through the paper-thin condo walls.  I’m pretty sure Cici was not looking for that kind of response. She was not laughing so I shoveled the laughter back into my mouth and steadied my voice.  “Explain, please?”

And she did, in great detail…

CICI: I use the word boyfriend very loosely.  I still had feelings for another man. Besides, I wasn’t sure if this new boyfriend was solely seeing me or if he had others between the sheets. 

After meeting online and going through several months of the ritualistic phone calls, texting, sexting, dates, dinners, and eventually meeting his young son, I was asked if I wanted to spend the night. Hmmmmm? Normally, that question is usually followed by an immediate yes,  but something was holding me back.

This new guy was one of those single dads who allowed his son to share his king-sized bed. We talked about this on more than one occasion. I wasn’t sure where I’d be sleeping, since I knew his son would be home that night. After a short hiccup in time, I said yes to his offer. I clearly did not think that a sixty-year-old man would expect a woman in her fifties to sleep anywhere but next to him, so I refrained from asking about the sleeping arrangements.

I was wrong. Instead of having his son spend the night in his own bed,  I was given the infamous puppy dog eyes and asked if I would not mind sleeping in his son’s room until he had a chance to have a chat with him. Is it crazy to think that he would have considered all the logistics prior to my arrival?  I didn’t know what to do. It was late and we had already had a few glasses of wine. Suddenly, surprising myself, I agreed.

Pecking him on the cheek with a simple good night kiss, I trotted down the hall, leaving the sexy lingerie I packed exactly where it was: in my overnight bag. Mumbling under my breath at how silly I felt, I pulled back the blanket on the twin bed and saw that I’d be spending the night with Woody. I could do nothing but laugh out loud. Hey, I’m the first person to admit that I love going to bed on top of a woody but NOT when the woody I’m referring to is the Woody from Toy Story!!

Yes, there I was in my mid-fifties and sleeping alone, down the hall from my boyfriend, in a twin-sized bed with Toy Story sheets and Darth Vader, Mario Brothers, and Pokémon on the walls above.  I felt like I was in a twilight zone of animated characters. Was I going to have to check for monsters under the bed?

Unfortunately, this was NOT a one-off occasion. Not only was I surprised to find myself repeatedly sleeping with my woody-less Woody, but I was shocked that I had allowed myself to set this precedent. What was I doing? 

Several weeks followed where I continued to sleep with Woody and his son continued to sleep with him. Clearly, he didn’t talk to his son so I decided to spend fewer nights down the hall and more nights downtown at my beautiful condo in the city hoping that he’d take the hint sooner than later. But he didn’t, so I finally spoke up and he reluctantly agreed to let me sleep in his bed while his son slept with Woody. I wondered why do we, any of us single women, put up with this bullshit?

My friend Cici is normally the voice of reason for my less-than-stellar dating stories. This time it was my turn to be the therapist…only I couldn’t stop laughing. I cracked a Woody Woodpecker joke and Cici laughed too. I’m excited to say that Cici will keep us posted as to the end of this cartoon adventure as well as many of her other dating escapades.

Stay tuned!


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