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Ask E. Jean For DearSugar: Does He Have True Feelings For Me?

Dear E. Jean,

I’m an elegant, attractive, educated and well-spoken 37-year-old woman. After nothing but eight long years of dating horror stories, three months ago I met a really attractive, sexy, open, bright, educated, and interesting 40-year-old man who was well raised and comes from a very nice family.

Since then we have been seeing each other up to three to four times a week, including sleepovers at both my house and his. Given that we both talk openly with one another about desiring marriage and a family, we realize the need, and share the same interest in spending lots of quality time together. We also realize that by doing so, we have put our relationship on a rather fast track. That can be an exciting thing to do, but it can have some major pitfalls too that are rather unexpected.

So, the major issue we are contending with has to do with altogether too frequent discussion and many detailed references to past relationships — on both sides. Honestly, my new man opened this line of communication with me very early into our relationship. I believed at that time, and appreciated, that it was purely for informational purposes — not to make me jealous and certainly not to showboat. In turn, I felt safe opening up about my past heartbreaks in order to let him know he was in good company, but that I was serious minded about him and what we could build together based on what lessons we had cultivated from our past choices and subsequent disappointments.

But now, three months later, I am growing increasingly concerned by his constant references to not only the most recent failed relationship (nothing more than an extended "Summer fling" type of love affair with a seriously-troubled woman in her mid-30s), but also to the many women he has dated over the last 20 years. How he remembers so much detail is beyond me. I can scarcely recall what any of my exes looked like in the nude, nor do I care to recall for that matter. I have pointed out several times how much better it would be for me, and for us, to converse about more interesting and more appropriate things. We do, by the way, laugh often and have a wide range of topics that we chat about. And he has been agreeable each time to my request. But then, at some point soon after, he launches into yet another story or analysis of what might have been wrong with so andso or how hurt he was when his attempts to help and/or intervene with this one or that one failed. To me, he seems hung up on the past failed relationships.

But the most damaging thing of all is that he provides me with far too much detail about past sexual matters. Sometimes he tells me that sex with so and so was awful, then he recants and says that in the beginning with her he actually really enjoyed it. It is becoming more clear to me as I grow to know him that almost every single lady he has been with since he was in high school had serious emotional and/or psychological problems. We're talking about family histories of severe alcoholism and physical abuse, women with eating disorders, girlfriends who may have been sexually abused by parental figures, rape, neglect, poverty, etc.

Yet again, this is just the beginning so


His most recent ex-girlfriend currently works as a high-school special education teacher, but at night and on weekends she sells drugs (pot, pills) out of her basement, to some of these same students she teaches by day!

My most recent mistake was a relationship with a man I came to view as secretive, commitment phobic, and probably living some kind of double life. I think the whole affair was one great big lie. Admittedly, it was a traumatic bond and a most painful experience for me. It has now been a year since I ended that nightmare, and sufficient time has passed so that I am more than ready, not to mention eager, to move on.

My new man, however, did not make a clean break from his most recent affair with the teacher, and when he met me he was still interacting with her. I cannot be sure how often. He finally informed me last week that he recently received a long-winded letter from her, filled to the brim with apologetic words and sorrowful language and leaving no doubt in my mind that she would like to pick it up where they left off and try again. He insists that he is over her, well aware that he'd be stupid to ever go back to her, that he is happy with me, that I blow her out of the ballpark in terms of just about everything. But my anxiety grows by the day and I am uncomfortable and uncertain of his true feelings for me, and for her. I have an impossible time anymore taking a man at his word. Burned a few too many times I guess. Help!!! — Connected in Buffalo

Buffalo, My Luv,

The man is a giant ass.

His being an ass, however, is beside the point. You must deal with the genuine travesty here, which is this: You’ve told us that his “most recent” girlfriend is a special education teacher, and that she’s selling drugs to kids — not only to kids — but to her special kids who need extra care.

This is murderous! The drugs she sells to the kids may interact with their medications. The effects of the interactions — memory loss, hallucinations, convulsions, seizures, brain damage, car crashes, death — if I listed just the obvious ones would take up the whole page here on DearSugar. So call the police at once. Also alert the Board of Education. The women needs to be in jail by tonight.

I’ve never heard of such a weak, deluded, manipulative, talky-talky, embarrassing excuse for a man in my life.

That this “bright, educated, and interesting” boyfriend of yours didn’t stop his drug-pushing “Summer fling” from imperiling the children in her care tells me everything I need to know about him.

This is not a man a smart woman would ever consider as a husband and father. Underneath that “nice family” veneer, he’s a 40-year-old narcissistic pantywaist. He’s so involved with himself and all the sex he had with screwed-up, alcoholic, sexually-abused women in the past, he will never see you for the healthy, worthy, lovely woman who you are.

Get rid of him, Miss Buffalo! You can do a thousand times better.

To see more advice from E. Jean, visit Elle magazine and

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