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Why does my boyfriend seem obsessed with a woman he hasn't seen for a few years?

Tagged as: Crushes, Dating, Friends, Social Media, The ex-factor, Troubled relationships, Trust issues<< Previous question   Next question >>
Question - (18 November 2019) 19 Answers - (Newest, 29 April 2020)
A female United States age 36-40, anonymous writes:

Hello, so I have been working with my boyfriend on and off helping him out in some of his work projects and he pays me, so he gave me his work laptop, not personal and I was working from there, so I remember I needed to search for a word meaning on google so I opened up mozilla and went to the google bar and when I began typing, his search history shows up and I can see that he typed the name of this woman he went out a couple of times with( nothing serious that is) they were just getting to know each other, but there was never a relationship between them.

They happened to have met in their work environment in 2017, he talked to me about her a couple of times of how beautiful, supermodel looking she was and that she had this great management job in a luxury building residential ( this is were they actually met) so I started feeling a little insecure and jealous because he talked so highly about her, physically speaking that is yet he told me she was a diva and was always flirting with everybody and other negative aspects about her.

The times that he has mentioned this woman to me, he would always start with:” this girl is so pretty, she looks like a model, that all the women that lived there always told her what an amazing hourglass body she had, that all these rich man driving expensive cars where after her, sending her flowers, messages and so on and then he would start saying all her negative traits and why he did not like her anymore and that she was empty, was too much of a diva and that he did see her true colors.

He told me that he was very glad that god took her out of his way, nevertheless he still has her in facebook and for some reason he always mentions the building were she worked in, or thinks that some random person lives there, so he always ends up mentioning it. He does not know in any way shape or form that I am aware that he has her in facebook and that I know her name as well.

And now I found out he has searched for her on google on several occasions ( about some months ago and now recently) ,why would this be? Is he still intrigued by this girl after 2 years or he is somewhat still curious, aggravated about her and the fact that nothing happened between them.

Should I ask him about this? What can I do to understand the reason why he is searching for her. It does not even make sense because he has her facebook. I have a close friend that knows her ex bf and knows her as well and according to my friend she works on another even more luxurious building now.

Why so much obsession with the building, this woman, at least this is what I feel here. this seems like if he was deeply impacted by all of this in that particular moment in his life and for some reason he can’t get over it.

View related questions: facebook, flirt, flowers, her ex, insecure, jealous

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A reader, anonymous, writes (29 April 2020):

I really don't see anything to worry about in this most recent post. I think you are spoiling for a fight; and anything even remotely related to that woman, and you go off.

Sorry, I defer to Honeypie. I'm not getting through to you, and your jealousy and insecurity towards this woman is impenetrable.

You're smart, articulate, and the guy is still with you. You see he hasn't said anything to the woman in the last three years; and you're still waiting to pounce the minute she's mentioned. I told you, he likes it when you're jealous; and he messes with you. He winds you up like a toy, and you bippity-bop all over the place about this woman.

Sweetheart, stay safe. I wish you the very best.

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A reader, anonymous, writes (29 April 2020):

This is verified as being by the original poster of the question

@WiseOwLE, Hello everyone, I hope everyone is doing fine and it’s ok, I have had been busy before quarantine had to travel, that I was not able to do a little update: So at the beginning of this year I decided to talk to him about this woman instead he mentioned her again In feb as I stated in my last post , so at the end of February we were in a hotel I traveled with him for his job, so one of those days being there, he went to shower he left his cell phone in the bed and all of a sudden it lights up and it was facebook messenger message, so my curiosity killed me and I had to check.

So hold on tight it was this woman , they had text for nearly 3 years, and all of a sudden she says: hi how are you? I know it’s not your birthday but I wanted to say hi, I was in shock cause you can see in the conversation window that they had not talked since when we started going out, that he wished her a happy birthday and that’s it.

What caught my eye is that he had not replied at it was like the third day since this girl had send the message( so she sent it on a Monday and he Replied on a Thursday ) he replied:” Hi how are you,I hope you are doing very good and I wish u all the best).

So I felt like I needed to tell him in a natural way that I had seen his phone light up that day and it was a facebook message and so on, so When I told him he was like:” its nothing important, neither you should worry about her, I met this girl like 3 years ago and have not talked to her ever since. So i just said in a very nice way to keep her at arm length :” Hi how are you I hope you are doing very good and I wish u all the best). its basically like brushing her off in a nice way, so no more conversations lies ahead or anything,

So he says to me that he did not feel the need to engage in a conversation with her, thats why he did not tell her” oh I’m great and happy, I have a girlfriend which is 17 years younger than me. He said this was unnecessary and would be a SLAP in the face for this girl and would ultimately make her feel bad ( she is 42) I am (32).

To me it sounded shitty!,why not tell her, he didn’t even have to tell her I was 17 years younger than him, just that he is happy, has a girlfriend and that’s it.

Another thing I found weird is that I have a friends cousin that works in the new building where this girl happens to work at now,YUP little world that we live in huh, (and my boyfriend knows exactly this is the new building where she works at, I mean he has her on facebook and she publish photos of this building and mentions it and what not, he always says negative comments of this new building that she works in ( he says it looks weird, that is ugly in his opinion, nothing special etc) .

So in regards to his negative comments of this building,I told him that my friends cousin works there as the Spa Director and said that it was a very luxurious building but nothing special or anything different than all the other luxurious building in the city.

So a week before quarantine we went to a beautiful outdoor park and this building is in front of this park, it was a Saturday, so when we were leaving I had to go to the bathroom to pee, so as soon as we are walking in front of this building to go get the car he says very naturally: Oh why don’t you go tell your friend in the building to let you go use the bathroom , she’s your friend right” I was lost for words, I was like she us my friends cousin, I don’t know her personally, so I insisted and we left.

Now what do you think about this ? Too much right.

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A reader, anonymous, writes (18 February 2020):

Aren't you getting the impression that he's messing with you? He has discovered you're insecure and harbor a deep jealousy for this girl. He's probably making up stories and exaggerations just to make you squirm!

He knows it gets you going, and I think he's triggering you. He's pressing your buttons! I guess no matter what Honeypie and I say, he's the one who has his finger on your trigger.

You'll just have to press through this until you become immune to it. You'll develop a tolerance over time; but if you overreact, you give him fuel to mess with your head. He's getting his kicks and thrills at your expense!

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A reader, anonymous, writes (17 February 2020):

This is verified as being by the original poster of the question

@ WiseOwlE UPDATE: Here we go again, he mentioned her again, but it was my kind of my fault cause we were talking about having chemistry with someone, and I told him the story of a good friend of mine, and he had the exact same happen to him, except that he was telling me that he was connected emotionally to her, that they had chemistry but they had a deal he would not have sex with her due to the fact that she asked for it because she was vulnerable because her boyfriend at that time broke up with her, left her for this other girl and got married little after breaking up with her.

So he has the nerve to explicitly tell me, she was in a bra and panties with this amazing body, and he had boxers on, they were kissing, cuddling and nothing else happened because they made a deal they wouldn’t have sex until a little more ahead.

And again tells me with an insisting manner, that this is really precious, that she had a whole bunch of men after her, she has this amazing body of working out at the gym, this work position, etc etc, and he always seems frustrated or almost bitter when TALKING ABOUT IT, about it, I wonder why!! They had nothing serious, just going out and getting to know each other.

I think he is somewhat frustrated because he did want to have sex with her but due to respect he did not. He sounded intense about this, like somewhat bitter.

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A reader, anonymous, writes (3 January 2020):

This is verified as being by the original poster of the question

@Honeypie UPDATE: I just found out they did not meet for the first time on February 2017, they actually met since August 2016, no wonder he has such obsession and when they met, she had a huge ring, then when they saw each other again on February 2017 she did not have the ring anymore and that’s when she told my bf that her bf had dumped her fir another girl, who happened to be his ex. So she was devastated, plus a month after dumping her, he married this girl. Imagine how traumatic this was for her.

Still I think he is obsessed about a person he was just getting to onow and went out of couple of times, and slept with her without sex ( I found out this too).

the weird thing is that be told me that he could not have sex with her like he fid not want to do it, especially knowing that she was vulnerable after her bf dumped her, so he even questioned himself and talked to a good friend of him of why he did not have sex, with her being such a wanted girl by all the man( according to my bf), and so beautiful and blah blah.....

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A reader, anonymous, writes (20 December 2019):

Well, at some point you'll either settle-down and have a happy relationship; or she'll always be a pebble in your shoe, and your nemesis.

If being with him is all about her, maybe you should let him go.

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A reader, anonymous, writes (19 December 2019):

This is verified as being by the original poster of the question

@WiseOwLE, I recently found out, they first met on August of 2016, not Feb 2017, and they actually did sleep together, cause in a message she asked him,” was I comfy to sleep with? What can this possibly mean? It’s obvious that they did have sex.

Maybe they both lost interest, plus they send my bf to another country during that time, so maybe she lost attraction towards him.

And maybe there is more to the story that I don’t know.

I just feel he is obsessed and frustrated with this woman, for some odd reason.

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A female reader, Honeypie United States +, writes (23 November 2019):

Honeypie agony auntI can't imagine having a partner that bangs on and on about an ex or an "almost ex" (in your case as nothing REALLY happened or worked out). But someone who KEEP talking about an ex, I always feel like, they aren't OVER that ex.

Yes, curiosity is also a big thing. I don't look up anyone from my past. Mostly because anyone I am still thinking about or talking to, are still in my life one way or another. I'm talking to them.

I honestly get WHY you question his behavior, but the only ONE who can really answer the question is him.

And the BEST time to bring it up is when HE brings her up, just simply say - Do you realize how MUCH you talk about this woman you supposedly don't like, what is that all about? And why do you think I'm interested in hearing about her?

Those would be good and valid questions.

Would he answer them? I don't know.

CAN he answer them, maybe, maybe not.

The things is HIM bringing her up as a "apparently interesting" topic is making you go HMMMM.. what is it about THIS one woman that makes him do that?

So it adds NOTHING positive to conversations or your relationship. It's like someone talking about diarrhea at the dinner table... it's just not going to HELP anyone enjoy dinner, is it?

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A reader, anonymous, writes (22 November 2019):

Sweetheart, don't let this woman become a thorn in your side. You go to that event! Seems this woman is contagious!!! First you accuse him of being too obsessed with the thought of her, and now you seem a little obsessed.

Work on whatever insecurities or weaknesses you feel you have in your relationship. You've already made it known to your boyfriend that you're uncomfortable with the frequency of the mention of this woman; and if from time to time you need to remind him to drop the subject...FEEL FREE TO DO SO! "That's enough about her, you have a girlfriend!!!" If you have to blast this reminder every-time she comes up, sobeit!

You both need to sit-down and ask each other to get this female out of your relationship; so you "both" can move on.

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A reader, anonymous, writes (22 November 2019):

This is verified as being by the original poster of the question

@Honeypie That is right!, btw just to make this clear this girl is pretty , I in no way shape or form want this post to sound like I am belittling her, it’s just that to the people close around me that have seen her pictures, see her just pretty, nothing wow about this girl, neither super model looking as he sees her, cause the way my bf described this girl to me is as she is the IT most beautiful creature he has seen in this world, I thought he was referring to a brooke shields type of girl, then when I saw her pics out of curiosity of course, I was like: oh yeah she is pretty, but not what I expected her to look like.

Another thing is that I was not aware of is that a lot of girls use tons of filters nowadays and as I have seen she uses lots of filters, so like my friend said we would have to see her live and in person to see what she is all about or what he truly saw in her.

Lets also take in consideration that her job and all the “supposedly” man that are after her makes her seem more interesting and a trophy like girl.

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A reader, anonymous, writes (22 November 2019):

This is verified as being by the original poster of the question

My friend who happens to be a psychologist as I mentioned before, told me that also due to the age gap and that I am younger than him, he will say all these stuff to keep me guessing and feeling insecure, since I am very pretty it’s like he almost wants this girl and I to have some sort of competition and this is why he threw all this beauty remarks of her to belittle me and keep me thinking, oh wow he went out with a girl that he thinks looks like a model and thereby keep the mystery on.

Sometimes I feel as if he would love me to be her or something. Or wants me to convert into her. Just me thinking if this could be it.

Also my friend told me to go to the event, to dress to impress and see what his reaction will be when he sees her.

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A female reader, anonymous, writes (21 November 2019):

I am going to be completely honest here, as almost the exact same situation happened to me with a now ex.

I think he IS looking her up because he finds her hot and sexy, and wants to look more at her for his pleasure.

To be honest I think it is more common than not nowadays, that men have access to whoever they like at the tips of their fingers on social media, that most men are probably doing this, even most men married or in relationships are still doing this (just looking up pics of women they used to find sexy in real life), BUT many men are better at covering their tracks.

Does it mean something serious? No, I don't think so. I think it is an indication of what almost all men do, which is fantasize about women who are not their own partners from time to time.

BUT now that you KNOW, will it be too much?

In my situation YES it was. I could accept intellectually this is what many men do and it wasn't that serious, but I KNEW about the googling and pining and facebook stalking of the sexy ex and I could not personally handle it anymore so I dumped him.

What you choose to do it is up to you. I DO think it is also very insensitive of him to talk about her beauty and her curves to you. He seems a little fixated and he can't control what comes out of his mouth. I would confront him about what you saw on his search and break up with him for your own sanity.

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A reader, anonymous, writes (21 November 2019):

This is verified as being by the original poster of the question

@WiseOwLE it’s like an ego thing going on with him, I actually told this situation to a good friend of mine that studied psychology and she says that she feels that there is more to this story, like maybe they did not have a relationship but since they saw each other everyday during the time he worked on the building that she works in perhaps, he got very excited about this whole situation with her and went too deep in based on looks and like you said the fact that every rich/ millionaire men was chasing after her, he somehow felt the winner that she indeed liked him, flirt with him. And went out with him.

But then he realized she was not what he imagined, she was just looks, a diva, and shallow perhaps.

Another thing he told me is that they almost had sex, mind you when he met this girl her ego was really hurt, her boyfriend had just dumped her for another woman and then married that woman right away, so I bet this was a low blow for this girl. So in my mind heartbroken women (some) tend to do this thing of looking for affection just to alleviate their hurt ego. So one night they went out they went to my boyfriends apt, drink wine, dance and almost had sex BUT according to my boyfriend he rejected her, cause when they first went out she cried to him and told him “ please don’t play with me or treat me like that man or men did. So this is why he rejected her and they did not end up having sex.

And then the day after this when they saw each other at work he recalls that she gave him this look of hatred and he knew that it was not going any further, like if she was really pissed off. Then they grew apart, then started talking again, but it just did not go anywhere at all. I guess she lost interest in him after what happened and he realized he was getting to hot and heavy with her and she was just emotionally unavailable plus very hurt about her being dumped by her ex.

I’m in shock right now cause there is an event that I want my boyfriend and I to go to for a long time now and I signed up for it in facebook events, and she happens to be going to this same event as well. Should I goor not? My friend told me to get al glammed up and what his reaction will be when he sees her.

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A female reader, anonymous, writes (21 November 2019):

Female Anon is bang on! It's the insecure men who lack self confidence who try purposely to keep us off balance in a relationship. They do it on purpose or at least subconsciously to keep us on our toes. To try harder to make them happy. And to try harder to keep them while all the while they are shitty people and shitty boyfriends. You Jeep a woman by raising her up, not knocking her down. Eventually enough is enough.

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A female reader, anonymous, writes (20 November 2019):

She rejected him. That's pretty obvious. So now he has a petty grievance and is googleing her and getting himself all worked up about what she's doing. If a man says a woman is beautiful but 'empty' or a bitch or whatever word he decides to use, he's usually just pissed off that she wasn't interested in him. And why is he always bringing her up to you? he wants you to feel bad. A girlfriend who feels bad works hard to keep her crappy man. Don't fall for it.

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A reader, anonymous, writes (19 November 2019):

Our looks and our behavior don't usually correlate; thus the adage, "never judge a book by it's cover!" Yet that doesn't mean you won't be intrigued by the book; even if you end-up hating how the story ends. You might even read the book again, to see if you'll have a different reaction to the ending.

He was captivated by her persona. Only to find-out her looks were deceiving. He still likes what he saw on the outside. So sue him!

He realizes he can't help but to admired her outer-appearance and charisma; but was disappointed to discover her beauty is only skin-deep. She is still an interesting-person; and her mystique may still be captivating. He still wonders how her story will end...or will it just keep coming-out in sequels. Will she fail, or will she catch herself a millionaire, or a billionaire? He doesn't play in the league she prefers to scout! So rather than feel rejected, cast aspersions on her character! Typical male-response to a bruised-ego! She may have somehow conveyed the point..."he's not her type!" Which will be translated into meaning not good enough. Not usually what it means; but take it anyway you want to.

I think a lot of people wonder what has happened to the people from their distant or recent past. She made a distinct impression. We wonder about those folks in particular who rejected us, broke our hearts, or left a bad-taste in our mouths. Sometimes we hope to find-out they got what's coming to them; or just want to know if maybe they will change for the better. Mean-spirited people wish doom and gloom on those who reject them; but wishing people to fail is a curse that boomerangs! To the devil's delight!

Googling people of the past (or your exes) is no worse than spying on your boyfriend's search history.

If you keep digging, you may find something you can't handle. If you're insecure, you'll be devastated if something scary crops-up! The main reason I don't dumpster-dive! I don't wanna find a body! Nor do I want to get all mucky and gooey from the big nasties that might be found below! Catch my drift?!!

I think this is harmless curiosity, and your insecurity is getting the better of you.

Now comes my disclaimer:

Words of advice aren't usually effective when people are insecure and have developed suspicions. The suspicion has to to keep festering, until it evolves into some deplorable act; or manifests as a series of accusations. We advise here, but how effective is it, or how seriously are we taken? My job is to make you think, and you reach your own conclusions. I study, research, ask questions, and I've lived through many experiences. As a fellow human-being, I can relate. When a stubborn-emotion hits me; I've got to see it through, and then deal with the consequences.

He's curious about her, and you're curious as to why? You can ask, but you're probably more likely to reach a negative-conclusion; before giving him any benefit of the doubt. It all depends on how much you trust him. He's a dummy! He doesn't know when to stop driving at an issue until he makes somebody upset!

Jealousy is normal, but it is abnormal when you become paranoid and overly-suspicious.

In general, or better to say, that it is arguable; that when women are jealous and insecure, they have to see it through to the end. Either by sabotaging their relationship; or letting ill-will and suspicion so overwhelm them, that they are never secure in any relationship. No matter how good it is.

Men will usually try to pretend things don't bother us; while reacting stupidly and aggressively. I guess you will have to ask him why is he so damned intrigued about some female who has long forgotten that he even exists? Then he will try and contrive some lame-excuse that you will either buy, or you won't! I guess we'll have to wait until the sequel to find-out how your story ends!

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A reader, anonymous, writes (19 November 2019):

In my experience, men who talk about how beautiful, smart, etc.their exes are in dating relationships do want you to feel some insecurity. It's as if they're saying I could have had her but....(fill in the blanks).

Some curiosity is natural, but googling several times and still having her on facebook means he has not truly let go of this woman. I find it a bit odd that people here will tell others if you're done with this person block and delete them on phones, social media, etc. But now somehow, it's okay for your boyfriend to have not done this in the case of this particular woman whom he had only dated a few time.

I'd be curious to know if God took her out of his way or if she dumped him. I highly doubt God has that much interest in our relationships.

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A female reader, anonymous, writes (18 November 2019):

Same female who has posted about her boyfriends ex several times on here but you word it different every time but I can tell it is you. You have been given endless and in depth advice on here, why dont you take it in?

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A female reader, Honeypie United States +, writes (18 November 2019):

Honeypie agony auntI'd guess curiosity.

People are curious by nature, it's a fact. My teenage girls were spending 45 minutes Facebook-stalking someone from their high school. And another 45 minutes doing the same to show our new "daughter" (we have taken over the responsibilities for an exchange student as her former family failed her) their various friends so that SHE can recognize who is who, before they went to a social event.

It was partly out of curiosity and partly to make things just EASIER for her.

I don't know how often I have heard of people who check out their new partner's ex, family or friends mostly DUE to curiosity. Sometimes to compare themselves (for whatever reason), but I think mostly curiosity.

I don't think it means he is OBSESSED with her, but he might be curious if she is (for instance) still working where she was working, still single or perhaps dating one of those rick dudes who hit on her.

I don't think he would BE with you, if SHE was the one he wanted to be with.

Why he still TALKS about her, I am not sure. I think it's partly disappointment that he was temporarily blinded by her looks until he got a taste of her not-so-pleasant personality.

People have this odd notion that someone who is pretty or good looking SHOULD also be a great person. That is not how it works. I digress.

Lastly, he might be keeping tabs on her in hopes that she fails spectacularly. If things didn't end all that well for them. Schadenfreude (German)/skadefro (Danish), are good words for it, which basically means, pleasure derived by someone from another person's misfortune.

However, WHY not ASK him, next time he bring her up? Why he seems so interested in her still. He might not be aware of doing it.

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