Torn up over a loser

So, this last spring after coming back from a project for my company abroad I met a man at a store and he approached me with compliments and we exchanged numbers. We went on a date, our only date really, and he took me to a divvy bar that was kinda sleazy (of all the places he could take me in an upscale neighborhood) and when I told him I was 40 he looked disgusted but then told me he was 42. He told me he wants someone younger, he works in Hollywood as a cameraman and has access to 19-year old actresses. Then, despite being kind of low quality there was a deep attraction I felt to him and he began complimenting me and essentially trying to let him come home with me. I didn’t let him, and he never called again. I mean I am a successful graduate level professional with friends who are also the same and have, in the past, only dated like-minded individuals (my deceased fiancée was a surgeon). I couldn’t get this man off my mind despite the fact that I KNOW we had nothing in common, that I thought he was uneducated and drank too much and was a total mismatch and not even good-looking to me, so I texted him over and over and finally, I offered to have sex with him just in the hopes that he would ask me out again. And he did and when I went there was a lady at the bar with him and she said she was his married friend. THEN, when I went home with him, she came with him and showed up there at his house and asked if she could watch us. I said no and told her to leave and she did, and he said I should have not kicked out his friend. He said no big deal, he is kinky like that too and he wanted to see if I was up for that as his “friend” (a married woman with a child at home) wanted to. At that point, I was kind of creeped out by him, but my attraction took hold and we ended up sleeping together….it was not good sex. He lived close, I was starting a new good position I was promoted to and somehow the idea of him kept creeping up on me, so I kept on texting him and getting breadcrumbs. I went to his house a few more times and we had sex as friends with benefits (always with me initiating except the few nights he would call late at midnight asking me to come and cuddle with him when I couldn’t because I had to work the next day). Only one time I went there he was sober because his stomach hurt from so much alcohol use and the other time I went, he was wasted beyond recognition. I still texted him despite all though he NEVER asked me out, nothing. Finally, once I texted him about sex and he said he had found someone else (this after telling me he had no interest in relationships or anything and a week after asking me to come over). He is a man in debt up to his ears, who can barely pay the mortgage to his luxury home, and his Harley and other things. The woman he found is 26, and job hops from one bar to the other, and certainly not at all what would be called “good looking” while pretty much everyone I meet says I am very good looking (which he said over and over again). I see him on social media chasing her and spending his money (credit cards) on her which he never did on me. Basically, he acts in love with this woman but also looks like a crazy older man chasing a younger girl who is just having fun at his expense. I don’t know why I care so much about this, why I am thinking about him or about this at all, why I am so torn up but I feel depressed and am crying all day. I have self-esteem, it is not that, but why would a person like him affect someone so much? I have plenty of friends and family and friends keep saying he is garbage and a loser.

He is a playa, an alcoholic and a man who prefers younger women. You are making yourself available to him while he basically gives you zero attention. And you offered to have sex with him because you wanted him to date you?

Ask yourself, is this all I'm worth by chasing a man who treats me like dirt and who shows little to no interest in me? Girl it's time for you to pick your self esteem off the floor and block and delete him. You are worth so much more.

He is a playa, an alcoholic and a man who prefers younger women. You are making yourself available to him while he basically gives you zero attention. And you offered to have sex with him because you wanted him to date you?

 

Ask yourself, is this all I'm worth by chasing a man who treats me like dirt and who shows little to no interest in me? Girl it's time for you to pick your self esteem off the floor and block and delete him. You are worth so much more.

Agree with this and I think this is precisely why you should be honest with yourself about where your self esteem truly is and why you feel you have to prove yourself to this, as you say, loser. I’m going to guess that you’re lack of an explanation to all this because there’s really only one explanation. Just because someone is successful and beautiful doesn’t mean their mental and emotional health is all together.

It sounds like you are lonely, grieving and grasping at straws for affection. Some therapy would help a lot more than hookups with sleazy strangers.

I met a man at a store and he approached me with compliments and we exchanged numbers. We went on a date, our only date really, and he took me to a divvy bar that was kinda sleazy. when I told him I was 40 he looked disgusted. I was kind of creeped out by him, but my attraction took hold and we ended up sleeping together.

It seems that you can't handle rejection and when he messed with your head and told you that he prefers young girls to you, it triggered you into a frenzy of proving yourself to him and....of "winning" an imaginary competition with those younger women where he will chose you.....except it's all messed up and all in your head and all you are doing in reality is humiliating yourself bending over backwards chasing after a loser. I actually think the very part that you see him beneath you and he dared reject you is what's driving you the most if you are willing to be brutally honest with yourself.

Probably a really good idea to schedule some sessions with a good psychiatrist and address your grief, loneliness, and self esteem issues. Yes, you have major self esteem issues. If your self esteem and self respect were healthy, you would have rejected this guy yourself half way through the first date. This isn't about some magical chemistry, it's about you trying to prove something to yourself....except....it's self destructive and proves nothing at all. Please get yourself sorted and get the help that you need to do so.

It seems that you can't handle rejection and when he messed with your head and told you that he prefers young girls to you, it triggered you into a frenzy of proving yourself to him and....of "winning" an imaginary competition with those younger women where he will chose you.....except it's all messed up and all in your head and all you are doing in reality is humiliating yourself bending over backwards chasing after a loser. I actually think the very part that you see him beneath you and he dared reject you is what's driving you the most if you are willing to be brutally honest with yourself.

 

Probably a really good idea to schedule some sessions with a good psychiatrist and address your grief, loneliness, and self esteem issues. Yes, you have major self esteem issues. If your self esteem and self respect were healthy, you would have rejected this guy yourself half way through the first date. This isn't about some magical chemistry, it's about you trying to prove something to yourself....except....it's self destructive and proves nothing at all. Please get yourself sorted and get the help that you need to do so.

This EXACTLY. Somehow you allowed your emotions to control your actions here instead of taking a stand for yourself... not so good for the self-esteem.

At the end of the day I can understand how you feel as a woman in her 40's trying to date... it's definitely a different world then it was when we were in our 20's, not just because of technology but because of our age. Men our own age seem to have this desire to date younger women... some because they have kids and want someone willing to help them raise said children, some because they WANT kids and want a woman that can easily have them and some are just like this above a$$hat and think they will somehow feel younger if they date a younger woman.... at the end of the day, there is nothing we can do about how old we are... instead look at it as something to be proud of, and that you have worked hard for, and that you are deserving of someone that is on the same level as you.

Do not be thrown by this guy, there are and will be many guys like this... take that energy and channel it into being awesome and celebrating who you are now.

It seems that you can't handle rejection and when he messed with your head and told you that he prefers young girls to you, it triggered you into a frenzy of proving yourself to him and....of "winning" an imaginary competition with those younger women where he will chose you.....except it's all messed up and all in your head and all you are doing in reality is humiliating yourself bending over backwards chasing after a loser. I actually think the very part that you see him beneath you and he dared reject you is what's driving you the most if you are willing to be brutally honest with yourself.

 

Probably a really good idea to schedule some sessions with a good psychiatrist and address your grief, loneliness, and self esteem issues. Yes, you have major self esteem issues. If your self esteem and self respect were healthy, you would have rejected this guy yourself half way through the first date. This isn't about some magical chemistry, it's about you trying to prove something to yourself....except....it's self destructive and proves nothing at all. Please get yourself sorted and get the help that you need to do so.

Read this again and again.

Actually, to be perfectly honest, I don't really want him. I want the idea of him to be true, I want the relationship that could never be with him. It normally takes me about a month to stop looking up an ex's social media and a year or more to recover. The thing is, I had a great dad who has a great marriage with my mom and treats her with great love and kindness but somehow I am attracted to this kind of "bad" man and I don't know why.

This last year was a year of loss, of my life I built abroad when I got transferred back to a large US city that is much more isolating than where I lived before, my grandmother whom I was close to died, I lost the apartment I used to have and have to save to buy a new place. I felt like he could have been a ray of light but obviously that is not reality.

As for self-esteem, when I tell people my story, they say "but you are stunning" so I guess there is the idea that I am a good looking but somehow that doesn't give me much confidence because most men don't really, at the end of the day, care much about looks.

It doesn't sound like you repeatedly fall for "bad boys". It sounds like you are grieving, isolated, lonely and trying to fill voids, but not addressing any real issues in a productive manner. Therapy would help you unpack some of this. So would getting to a doctor for a physical to assess any medical/ mood etc. issues that may need medical treatment.

Also work on a self improvement plan to rebuild some confidence. Get in shape, update your looks, clothes, hair ,etc. Try to quit some bad habits if you have any. Get more involved socially where you are. Join some clubs groups, takes some classes courses, volunteer. Try to meet a better class of men and more like-minded friends. Get a good profile and pics on some better quality dating apps and start to message and meet men.

I am a successful graduate level professional with friends who are also the same and have, in the past, only dated like-minded individuals (my deceased fiancée was a surgeon).

“I want the idea of him to you true”

What’s this based on? Serious question because according to you he’s never done anything to show himself to be anything but a loser, your title is literally ‘torn up over a loser’ so which is it?

Is your ego in overdrive causing you to lie about the reality of what happened or is your ego on overdrive and causing you to reject the fact that although you’re successful and attractive your low self esteem and probable past, (we don’t know your whole story, that’s something to unpack with a therapist), is causing you to dive into disfunction and lap it up like a 10’course gormet meal.

You keep acting like your situation is some sort of annomoly and is a mystery how it happened, it’s only a mystery to you and if you allowed your ego to stand down you might see what the rest of us see. If it typically takes you a month to stop stalking men’s social media and a year to move on it might be time to recognize that that’s not normal. After a long and serious relationship or marriage sure, expected, after every dating expierience? Especially with the one you’re describing no, somethings off.

Actually, to be perfectly honest, I don't really want him. I want the idea of him to be true, I want the relationship that could never be with him. It normally takes me about a month to stop looking up an ex's social media and a year or more to recover. The thing is, I had a great dad who has a great marriage with my mom and treats her with great love and kindness but somehow I am attracted to this kind of "bad" man and I don't know why.

 

This last year was a year of loss, of my life I built abroad when I got transferred back to a large US city that is much more isolating than where I lived before, my grandmother whom I was close to died, I lost the apartment I used to have and have to save to buy a new place. I felt like he could have been a ray of light but obviously that is not reality.

 

As for self-esteem, when I tell people my story, they say "but you are stunning" so I guess there is the idea that I am a good looking but somehow that doesn't give me much confidence because most men don't really, at the end of the day, care much about looks.

That's correct, you don't actually want him, you want to win this imaginary competition you've pitted yourself into where he picks you over these younger women. That is a serious case of ego and damaged self esteem issues. Whether you are aware of it or not, the idea that you can win and control this gives you a boost, unfortunately, it's just a toxic mess and not really a boost at all. So I'll just echo other posters that you need to do some serious unpacking of what's really going on with you and also deal with your loneliness, moving, loss, grief in a healthier way than lowering yourself to chasing after a loser.