Skip Nav
40 Hilarious Costumes For the Funniest Couples
7 Reasons I Wish I Hadn't Taken My Husband's Last Name
The Top 15 Movies With "Cougar" Characters

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

Join The Conversation
snowysakurasky snowysakurasky 9 years
Cool, thanks for the details... Hope you are over it, if it were me I'd be trying to forget about him ASAP, like, I'd be ashamed to have been with such a loser kind of thing. Did anything happen to protect the children? Hope you can follow up with that... does anyone know how she can get that lady fired without putting herself at risk? Surely the lady's not in a gang or anything...
ichigo-ichie ichigo-ichie 9 years
Hi everyone. It's me. The Buffalo gal who wrote this account. Thank you, first of all, for so many truly wise and helpful comments. I especially like this new expression "narcissistic pantywaist". That very tidily sums it up. So you all understand, I wrote to E. Jean a couple of months ago about this guy, so a lot has occurred since then. At the time, I was, peculiarly, on the fence about him, which prompted me to write in the first place. I guess I was a little caught up in the situation and couldn't see it clearly enough. There were certainly several "red flags" and I am embarrassed to have looked past them. Simply, I expected more from a 40-year-old man than what I got, and it took me time to gather my wits. I had just about had enough when it came to all the gratuitous commentary about so many ex-gf's and the pornographic sexual references - like when he told me about once "getting it on with his gf on the picnic table at his mountain cabin". I definitely had enough when, after losing the excess 15 lbs I had on me within 2 months, he told me how relieved he was because when he met me he thought I was "obese". He explained that now that my ass was getting smaller, he was growing so much more sexually attracted to me. What an a--hole. One time, after an arduous 3-hour bike ride together one Sunday afternoon (whereby I kicked HIS fat butt), and we were having a small turkey sandwich together at my house, he leaned over to pinch flesh on my back underneath my braline. I gave him a penetrating stare square in the face and asked him what the heck that was for. With a grave look on his face, he asked me, "Have you gained weight back?". I almost spit my mouthful of chewed up turkey and lettuce at him and I had a strong desire to kick him you know where. Instead, I maintained my composure and told him sweetly that he needed to sit down with a therapist. I eventually told him he's got a sick orientation to screwed up, broken women and that my guess was that by getting involved with losers, it makes him feel like a winner. I also told him I am not a loser, and that by calling attention to any physical flaws I might have does not turn me into another one of his losers. To the gal who anticipated he would turn tables on me, you are so right. He actually started to tell me I came from a dysfunctional family and that I was unfit for marriage and motherhood on account of it. Ladies, have you ever read either "How to Spot a Dangerous Man" or "Maybe He's Just a Jerk"? Well, after I gave this dangerous jerk the royal heave-ho, I read both and learned that I was dating an emotionally/psychologically abusive narcissistic pantywaist and sleazy lover. Before I go, and I really hope to read more comments because this is so validating, about the skanky drug pushing ex-gf: I had someone make an anonymous call to the authorities, including the Board of Ed, to turn her sick ass in. It is a small world here and I live alone. So, while I want justice for all of those special students, I want to be safe at the same time, hence the need for anonymity.
JaimeLeah526 JaimeLeah526 9 years
He's only telling you this because he needs someone to talk to and validate his feelings. He's never had a successful relationship, you don't want to marry this man. If he's only ever been with fucked up woman, what is wrong with you? He wouldn't be with you if he didn't have a story to tell to the next girl about how screwed up you were. You need to consider that for a moment. People in relationships are not supposed to talk so much about their past relationships, especially not about the sex life. Tell him to get a therapist and talk to HIM about it.
sparklestar sparklestar 9 years
You need to notify the police about his ex-girlfriend NOW. Then you need to get the hell away from him. I've been with guys before who are hung up on their past relationships and it's just so DRAINING. Like E Jean said... find somebody who can appreciate you without you needing to be a broken excuse for a woman first!
Janine22 Janine22 9 years
I 100% agree with E.Jean here. Also, the fact that he cannot help himself but to go on and on about his exes is just rude, disrespectful to you, and also shows you that he is not over them. I am suspecting he was still involved with his last ex when he met you, by what you have written. Trust your instincts on this one!!!! If you feel that it is not right, then believe your feelings. I am also suspicious of a man that has not been married or had children by that age.
MisterPinkNoTip MisterPinkNoTip 9 years
E. Jean's response was perfection, again. Go E. Jean!
juicylove juicylove 9 years
also, bad things his friends (or ex gf in this case) get into.
juicylove juicylove 9 years
this sounds suspiciously like a few points off the list of "things he should never mention" post. talking about past hookups, that girl he tried to make it work with etc..
snowysakurasky snowysakurasky 9 years
I was actually going to say try to work it out with a couples therapist (who would recommend he get his own therapy on the side) until i realize i missed the part about selling drugs to special needs students. E. Jean rules!
snowysakurasky snowysakurasky 9 years
snowysakurasky snowysakurasky 9 years
Asia84 Asia84 9 years
I didn't read E. Jean's response (i've suffered enough with all the reading). I feel like this: he likes drama. he likes the girl who is just that...a girl. you are a full grown woman. he would've dumped you on some phony crap like you're too independent, or too head strong... you don't give enough. the truth is, you're not some needy freak. he sounds like he will take you through the wringer. i think you have kissed enough toads to see this. all in all, RUN. tell him you need to go your separate ways. you will be able to find somebody else . . .at your age, you're like the perfect wine. don't waste your time with somebody who has issues.
GlowingMoon GlowingMoon 9 years
I agree with E. Jean. Ironically, in my past, I dealt with a man like that. Seriously, at first, I thought you and I knew the same man. On the outside, and on paper, he seemed great -- well educated, handsome, comes from a good family, earns a good living, etc. But the qualities stop there. It's truly a veneer. On the inside, and in my opinion, that's what he truly is, he's a narcissistic chauvinistic womanizer. Thankfully, we were never involved. He pursued me, but I just wanted us to be friends.
xoxoxx xoxoxx 9 years should called the cops on that fucked up teacher - god knows what kind of damage she's done to those babies.
Fallen85 Fallen85 9 years
All of his ex girlfriends since HIGHSCHOOL (40 minus 18 equals 22 years of bad girlfriends!!) has had serious emotional and/or psychological problems? Now... lets see here... he's 40, you make no mention of children or an exwife so he's never been married and never had kids, he dates women who deal drugs to children with mental handicaps and he complains constantly about the women in his past... hm.... someone grew up with an Oedipus complex, me thinks! The only constant in all of these failed relationships with these psychologically screwed up women has been... well.... HIM! Doesnt that tell you something? Out of all the men you've dated in your 38 years have ALL of them been completely screwed up? Some of them might have been jerks, some of them might have been great guys but just didnt mesh right, or great guys that decided you werent the one for them, others might have even been psychos... but ALL of them being completely emotionally and/or psychologically screwed up? I doubt it. This guy is messed up, he cant let go of last relationships, he is madly in love with himself and obviously enjoys the attention of any women... including drug dealing emotionally messed up psycho b!tches. He will ever see you for who you are when he is so distracted by himself. I know that you thought he would be "the one" but it sounds like your "inside voice" is screaming for you to tear the rose coloured glasses from your eyes and see who he really is: a "narcissistic pantywaist" Good luck.
Beauty Beauty 9 years
I now have to figure out how to incorporate "narcissistic pantywaist" into more conversations. Hilarious!
lawchick lawchick 9 years
Great answer E Jean. I'm so sorry to say this but your new man is a loser. I always think it's a bad sign when your new man goes on and on about how all his exes were "psychos." He'll be saying the same thing about you to his next girlfriend. Plus it's really disrespectful to you for him to talk about his sex life with his exes all the time! Run away!!
skigurl skigurl 9 years
E. Jean - telling it like it is since 1983
MartiniLush MartiniLush 9 years
I have to say, I am wondering where you are looking for men if this prick is a "good" guy!!
geebers geebers 9 years
Now for MY response haha - Like E.Jean said- the first thing that HORRIFIED me is that this woman is abusing her kids like that. PLEASE contact the authorities. And from what you wrote- how is this a "good" guy?? He sounds like a real doozy- any guy who has that many issues with his ex-gfs AND all of them had these problems...RUN! If anything- I bet when you leave him -he will tell his new girl how you had "commitment issues stemming from traumatic childhood". He sounds pathetic and you sound so much better than that. Let some other girl deal with his mess.
geebers geebers 9 years
Awesome response E.Jean - as always.
Sporky Sporky 9 years
Sounds like he needs a therapist to talk to instead of using you as one! I think despite you telling him you don't want to hear about it and him still talking about stuff like that, you should move on.
linb linb 9 years
Right on, E Jean. Sounds like there is a reason he is still single at 40.
Signs a Guy Is Interested in You
Disney Princess Zodiac Signs
Why You Should Wait to Have Sex
How to Know If You're in an Incompatible Relationship
From Our Partners
Latest Love
All the Latest From Ryan Reynolds