Dear DSO: “I’m a Ladies Man”

Dear DSO,

My story: Before I met my wife, I had sex with at least 200 different women. I worked at a night club for several years. It was like shooting fish in a barrel. I’m a pretty good looking guy and keep in good shape. I still work out five days a week. My friends all thought I had it made. I slept with some of the most gorgeous women you’ve ever seen. A couple of these women were actually kinda famous (my club was in Miami and we had lots of celebrities come in). 

I was working on my getting my CPA degree while working at the club at the same time. I didn’t want to be in the club world for the rest of my life. I’m actually good with money and I enjoy accounting. Most of the time the school work was done on the internet, but I had to go in every now and then for group work at the University. That’s where I met Karen. I eventually fell in love with her. We dated for about two years before I proposed to her. The entire time we were dating I was still working at the club and still sleeping with women. I felt awful about it. She had no idea. She used to be jealous, but never thought I would do anything. She trusted me. She’s never asked me about my experience with women, and I’ve never asked her about her past, either.

Karen comes from a really great family. That was something I really liked about her. My family was a mess. My dad cheated on my mom a lot and they got divorced. My mom ended up with three different guys after my dad. I was always embarrassed about my parents and I was glad to find a new family and a new set of parents that I could look up to. Her dad and I really got along.

I managed to stop sleeping around once we got married. It helped that I left the club and we both started our own accounting practice. We work from home. Karen got pregnant and we almost lost the baby. Thankfully everything ended up okay. Our child is now almost one year old.

The problem is that when we went through the stress with the baby, I started sleeping around again. I texted some women that I knew would be down for some fun and had sex with three of them. One of them I connect really well with and we slept together four times. 

Unfortunately, I was stupid and left my phone out and my wife saw messages from one of the women. She took the baby and went back to stay with her family. The family refuses to talk to me. She won’t answer my texts or calls. She just tells me to leave her alone.

I realize what I did hurt her a great deal. I had such a great thing going and I’ve let everyone down. I realize I’m just like my dad and it makes me furious. If I don’t get my wife and daughter back, I just want to move across the country and start all over.

I found your site because I was searching for stuff about “starting over” after cheating on my wife. I like your articles, but I know they’re not for guys like me. What would you tell somebody like me who wants to save his marriage and start over with his wife?”

Thanks for reading,


Dear Juan,

You’re right, I don’t typically receive emails from guys in your predicament. What’s interesting about your situation is how much it mirrors that of the majority of guys I talk to… but with the roles and genders reversed. Many men I talk to fell in love with girls who, they admit, were “trouble” or “had more red flags than a Chinese parade”, but they jumped into the relationship pool anyway. The women made them feel amazing.

These men persevere through more and more red flags. Eventually they get to the point of feeling like everything is secure and comfortable (usually after years of being married, having kids, moving to a new town, etc). Then… it happens. Their world collapses. At the time it was a giant surprise that sent their head spinning… but the later realize that it was so very predictable.

A lot of my thoughts on these situations can be summarized as, “Well… what the hell did you expect?!” I think I would say the same to your wife.

You’re a handsome ladies man. By virtue of your vast experience with women and your time at the club, you are probably a natural flirt and have REALLY great social skills. You’ve probably never met a stranger. This is insanely attractive to women. Your “normal” wife isn’t the first to fall for the hunky Lover who has a conga line of women in his wake.

It’s easy to write off a past like yours as being “cool” or “normal” for a good-looking and social guy. When we dig a little further, we see a broken little boy who is acting out the actions of his dysfunctional family. This boy BADLY wants the security and safety of a stable home life, but his deep-seated programming and inability to cope when shit hits the fan continuously pushes him in the wrong direction.

At this chapter in your life, you are not ready for a wife and kid. Let her go. She may come back… probably not.

Being a married family man takes a certain disposition and set of skills that you just DO NOT have right now at this time. You can work on you, and work really hard, but your wife may not come along for the ride. Your only hope is to put in the time and effort on yourself. Go get some help. Figure out why you do what it is you do and how you can prevent it in the future.

Good luck, my friend.