I’ve been dating someone I care, but something is severely wrong. He said he loved immediately after we met and became hyper attached, obsessed with me. He was very jealous and would accuse me of cheating if I went out with friends and didn’t text for a few hours. I managed to calm down his jealousy and to his credit, he stopped worrying about much 2 months into the relationship.

Sexually, he was into cuckholding and wanted me to talk about humiliating him and sleeping with guys in front of him, telling him he wasn’t allowed to sleep with me. He wanted to masturbate to me clothed. But he also claims emphatically that he enjoys sleeping with me more than anyone ever (which I believe). This created a paradox for me with the jealousy concerns however. Concurrently he talks obsessively about his ex-girlfriends who he also became obsessed with while dating. Literally he brings them up (some from over 14yrs ago) a few times a day.

The final “straw” was when I found out that he has been essentially online obsessing and masturbating (via social media) to nearly every woman he’s either slept with or has been interested in/rejected by all the while saying he’s just not that into sex. He insists that he’s just not that sexual of a person — but masturbates 1-3 times a day, and after just a few weeks of us sleeping together he started doing things like waking up in the night next to me and masturbating despite me asking him to wake me up so we could have sex. He frequently has problems getting an erection with other women and in his last relationship didn’t have sex with her more than 12-15 times in 2 years.

His father was very emotionally abusive, but he claims his mother was very caring and that his upbringing was fairly normal. But he’s 42 and has never had a relationship longer than 2-3 years and is consumed with dating and many women. He moves every 1-2 years. He also takes great pride in being socially popular. His sister is 40 and has never been in a relationship before. She’s also HIGHLY OCD and sterilizes her apartment.

I’d like to get information about what the issue might be, as it seems pretty serious.

A. Here are the things that concern me. He masturbates 1 to 3 times a day, yet claims that he does not have a high sex drive. He chooses to masturbate rather than to wake you up, as you have requested, to have sex with you. He talks about ex-girlfriend’s incessantly. According to your understanding, he became hyper-attached and obsessed with you at the very start of your relationship. He is 42 and has never had a relationship that has lasted longer than 2 to 3 years. The behavior of his sister appears odd to you. He takes great pride in being popular.

Altogether, this suggests that he is quite successful in shallow relationships but is a failure in deeper relationships. Shallow relationships are simple and not at all complex. They are much easier to maintain, little is asked of the participants in the relationship. Deeper relationships are more challenging. They require skills and abilities that are qualitatively different from that of the shallow relationship. A deeper relationship is not like water. A deeper relationship, when talking about water, is when 3 feet changes to 4 feet. It is the same thing, only more of it. A deeper or meaningful relationship, involves a qualitative change. We are not talking about simply more water as the relationship deepens but we are talking about moving from water to something different and thus a qualitative change. A deeper relationship is not simply “more” of a shallow relationship. Your boyfriend is successful and has the skills necessary to thrive in a shallow relationship. However, it appears, from your written description, that he does not possess the skills that are necessary to be successful in a deeper or more meaningful relationship.

It is reasonable to conclude that in his long dating history a number of relationships would have succeeded had he possessed the skills necessary to make them work once they changed from shallow to deep. Without professional help, it is very unlikely that he will develop the necessary skills. With professional help, there is a high probability that he can develop the necessary skills.

Please bear in mind that I have not had the opportunity to work with your boyfriend. I have not had the opportunity to ask him a single relevant question. I have only the words that you have chosen to write to me. Hopefully, it is quite obvious that I do not, nor does anyone else, have the ability to diagnose someone that they have never worked with professionally. I have attempted to share my professional knowledge with you. I have not attempted to advise you or diagnose your boyfriend. I would, if I could but as I have just explained, I can’t because it simply is impossible.

If your boyfriend will not enter therapy, you could make an appointment with a professional. Though the therapist that you see will still be limited because they are unable to work directly with your boyfriend, at least they would be able to question you in great depth and you would be able to provide them far more knowledge than was contained in the short email sent to this site. Please don’t think that I am blaming you for sending a short email. If it’d been twice as long, or even 10 times as long, it would not have been enough information to have enabled me to make a diagnosis or advise you with reasonable certainty.

I cannot diagnose or do therapy over the Internet. I would suggest that he or you or both, see someone locally who will have the ability to question and probe and do therapy or at least advise with reasonable certainty. Thanks for writing.

Dr. Kristina Randle