Some of the guys I was with in my newly single years I bump into every now and then. Some still show up in my DM’s every now and then, all these years later. I have so many regrets from this difficult yet fun part of my life.

On a scale of regret, from zero to ten, Joe was an eleven.

I was out with friends. Having a great time. Innately I love people and with a few drinks in me, I’m ridiculously friendly. I’ll bounce from table to table, chatting to anyone and everyone. This particular night I ended up at a table with a coworker and her husband.

Along came a friend of theirs, Joe. To be honest I was not even paying attention to Joe. Although I always liked older men, he was maybe a bit too old and not very attractive. But of course, we chatted quite a bit over our drinks.

He was newly separated from a lengthy marriage, kids grown and nearly my age. I think I felt sorry for him. He latched onto me like a lost puppy, a puppy I couldn’t shake. But there’s something powerful about feeling adored.

We ended up at my place. I felt mean, I didn’t want to lead him on, but I just wasn’t into him. Beyond the conversation anyway.

We slept side by side in my bed until morning but I made it clear nothing was going to happen between us and he respected that. I really give him credit for that too. A true gentleman.

I woke up with not just a hangover but feeling the hugest regret of my life. I really don’t like the thought of leading someone on just for nothing.

He asked for my number before he left and said he wanted to hangout again. He called me that same evening. A desperado. I couldn’t say no. I don’t know why. I just didn’t want to be mean. He suggested he come over with some pizza and beer. Okay. Not really my thing but okay, I’ll entertain it.

He definitely thought “date” two meant we were going to be getting close and I couldn’t get far enough away from him. He actually repulsed me and I’m not even sure why.

I think I made up a lie to get him to leave and when he texted later asking when we would see each other again, I said we wouldn’t.