It’s been a month since my great five-year-long relationship ended and it’s my fault. We were both in our mid-forties, got along, and had amazing sex three to four times a week. Yet I felt unsatisfied with the sex, as it was almost always “maintenance sex,” at least on my ex-partner’s side. While I found it enjoyable, I knew she often didn’t. Another reason for my dissatisfaction was her inability to converse about the things I am most passionate about: music, movies, anime, and the paranormal. Her interests were tax codes, insurance rates, and other administrative topics. It should also be noted that my ex was a heavy pot smoker due to terrible menstrual cramps and, as a consequence, I became a huge pothead.

I actually broke up with her after our first year, but we ended up getting back together after she texted to tell me how heartbroken she was. I loved her and felt terrible about the whole situation, so I caved. Afterall, I enjoyed my time with her, and, despite conversations that were often boring, the pot-fueled maintenance sex was amazing, and the cuddling afterward was nice.

Fast forward three years and an attractive woman in her twenties moves in next door and we quickly become friends. She would bring pastries over for my child (I’m a single dad) and once brought soup over when I had the flu. On one occasion she drunkenly knocked on my door late at night, wanting to hang out. I couldn’t, as I had my child at the time. Due to the dissatisfaction I had long felt about the maintenance sex that characterized my relationship, I was tempted to have sex with my neighbor, if she was interested. I told my girlfriend about the late-night incident, and she demanded that I no longer hang out with my neighbor. I agreed but soon I was hanging out with my neighbor behind my girlfriend’s back.

My girlfriend found out by snooping through my phone and broke up with me. I was devastated and begged for her to forgive me, which she did on the condition that I cease all contact with my young neighbor. I agreed and another (pleasant) year passed until I met another young woman who seemed to like me.

This young woman, also in her twenties, was interested in all the same things I am. Knowing I couldn’t trust myself, I made the difficult decision to break up with my girlfriend. When she left my house for what I thought would be the last time, I felt like I had destroyed a functional relationship. It wasn’t perfect — lack of common interests, uneven sex drives — but we enjoyed each other’s company. So, a week later I asked her to take me back again. She agreed. A few weeks later, I was again scheming to hang out with this twenty-something young woman. I was almost immediately busted by my girlfriend — she snooped and read my texts (this time on my laptop) — and upon discovering my betrayal, she screamed at me at the top of her lungs before slamming the door and exiting my life, this time, I fear, forever.

Will the regret and shame I feel ever go away? I’m utterly “maiden-less” now I’m utterly ‘maiden-less’ now and, in my mid 40's, am having a difficult time finding someone in my wheelhouse. I was kidding myself that two cute women in their twenties would be interested in a man like me. So, not only did I wreck a perfectly good relationship, in the end I wrecked it for nothing. There was no pussy at the end of this shit rainbow. Please, Dan, tell me something that will make me feel better about this flaming dumpster. Will I find my way? Or am I condemned to forever lay in the bed I shat?

Anonymous Magnum Subscriber

So, you didn’t actually cheat on your ex-girlfriend, right?

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