Recently, two women emailed me about difficult cohabitation situations with men. Both women admit to ignoring red flags in the early days of their respective relationships.

Jeanne emailed that she met a man online in 2015. In 2018, she allowed him to move in with her.

Jeanne said,His landlady knew he and I were dating; she called to tell me that he might ask to move in with me. She kicked him out of her house because of ‘lifestyle differences,’ namely that he was a hoarder and had boxes piled high in his bedroom.


“She was right. He did ask to move in with me. It was easy; just open the door and let him. I admit I ignored some red flags.

“I thought he would weed out the boxes before moving in. But no, the boxes came with him and into my garage and house. He has even more stuff in a neighbor’s garage.

“He is very quick to anger and is an incessant talker and takes over conversations and hates being interrupted or countered. Two wives left him; apparently, they hated being lectured to and that he was always right and having it his way.

“He refuses to get rid of the bicycle, motorcycle, and kayak. He isn’t going to use them as he’s in his late 70s and out of shape.  

“His flaws are too much for me; they killed my love for him. I didn’t like the person I had become — yelling and fighting back or shutting myself in my bedroom.

“We don’t have a cohabitation agreement. He says that I can’t kick him out, and the only way he will leave is if I sell my house. Maybe I should ask my lawyer! Getting him to move out is nearly impossible.”

Beth (not her true name), 70, wrote: “Sixteen months ago, I started dating an older gentleman (79). We met online at the beginning of COVID-19. We missed the dating process because of COVID shutdowns.

“We walked often, and I cooked for us and cooked for him before I went home. We Facetimed every night we weren’t together. He’d call eight times a day asking when I would come to his house. He asked me to marry him early on, but I said no.

“He wanted me to move in, but I said no. He started to fail physically, losing his balance and falling occasionally. I started going to doctor appointments with him. I went from girlfriend to caregiver in a few short months. Staying at his home for three months, I cooked and cleaned with no days off.

“He was very demanding of my time. He had brain surgery. I had to shower him. I started pushing back and told him when he got well, I was returning to my home. He asked me to stay another month.

“One day while he was on the phone, I packed and left. I felt guilty for leaving but knew no time would be a good time to leave. I am so burned out. I decided to just enjoy my life.”

Here are my seven lessons learned from these two situations.

Before cohabitating:


1. Heed red-flag warnings.

2. Trust your instincts.

3. Get to know the person well.

4. Don’t rush your decision.

5. Agree to a written exit plan before the move, in case it doesn’t work out.

6. Don’t do it just to save money.

7. Remember, moving in is easy; moving out is difficult.


For dating information, previous articles, or to sign up for Tom’s complimentary, weekly e-newsletter, go to

Have questions?

We are just a click away!