A
female
age
36-40,
anonymous
writes:I recently made contact with a guy from my high school from years ago. We talked for about a week, mostly through text, and made plans to meet up over the holidays, when he dropped a bombshell, and I need help sorting through it. Basically, he told me that last year, a homeless woman approached him. She was lost, so he invited her to spend the night. He says he is "paying it forward" for all the nice things people have done for him over the years, and she was cold and confused. She ended up staying for a while, and he found out she was using drugs. He says he had to call the cops on her 3 times due to domestic issues, but always took her back in out of pity. He says the relationship turned intimate and he felt she "taught him to love again after a failed marriage." He says now she just stops in every once in a while to shower, but that's it. She stopped in last night, and he called and left me a lengthy voicemail so I could hear their conversation. It was really weird, and the message was garbled and I could only hear that it was a female voice along with his. Could not make out what was actually being said.This story triggers a lot of things inside of me. How would you interpret this story, if someone you were interested in told this to you? Would you see red flags like me? Or am I being too sensitive?
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female
reader, anonymous, writes (25 November 2019): This guy sounds like a jerk. You're only seeing him through rose coloured glasses and are holding on to a fantasy version of him. Wake up and see the person in front of you. Before you let him hurt you because you are so desperate for some kind of escape. He is not a good guy.
A
female
reader, anonymous, writes (22 November 2019): Sounds a lot like he took advantage of someone who had very few options and no security. If he came on to her, how free do you think she would have felt to say no given that he was the only thing between her and being homeless?
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A
male
reader, no nonsense Aidan  +, writes (21 November 2019):
CindyCares is spot on with this one.
The flags are as red as red can be I’m afraid. Whatever way you look at it, it’s going to end in disaster. Let’s say we take him at his word: being a kindly soul, he took in a homeless woman and fell for her. She taught him how to love again after his failed marriage. He is still seeing her and letting her stay at his place, so if his story is true then he’s not over it and expects you to put up with him hanging out with someone he was in love with. Does that sound like someone who’s going to be committed and put you first?
Then there is the other view: he took her in and gave her a place to stay, found out that she is vulnerable and has a drug problem, and took advantage of her. That’s the view I’m inclined towards. You don’t have to have sex with someone just because you want to, but he did. That makes his actions rather less selfless. And you’re supposed to believe that she (who he may or may not have loved but certainly lusted after) just pops around for a shower because he left his voicemail recording while they were chatting? He’s hardly going to let it run while they are in the middle of having wild sex is he?
I’d quit while you’re ahead and let this guy go.
I wish you all the very best.
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A
female
reader, CindyCares  +, writes (21 November 2019):
 Most definitely a red flag. Very red.
So, he is " paying it forward ", uh ? That's one way to see it.
Another way is, he was / is sexually exploiting and taking advantage of a poor wreck of a not so lucid human being. He is / was making her pay for her supper through sexual favours. Now I am sure he did not put it in these terms, and does not see it this way, and I am not implying that he raped the woman ( although, how " informed " must have been her consent with a drug addiction and a visisble state of mental confusion,- that may be debatable ): my point is : what other option did have this homeless woman , if it was hinted / implied / even vaguely suggested that her welcome under this guy's roof, with heating, running water, food etc....was quite a bit linked to her being a good sport and playing nice and putting out on request ?....
And all the drama, the cops, the back and forth ?... Too dysfunctional for my tastes, even if it was actually out of the goodness of his heart , which to me is hard to believe. This seems such a BS , contrived story to me …. But, the problem is that , even it all was absolutely true and above board … it would make me seriously doubt of the soundness of his judgement, the balance of his mind, and the maturity of his life choices.
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A
female
reader, anonymous, writes (21 November 2019): I would be extremely worried and I would not continue having anything to do with him. A crush on highschool is very different to forming a relationship as an adult. This woman clearly has issues if she hasn't sorted herself out in three years and goes there to shower ? In my head I'd be concerned of his motives of letting her stay and then ending up sleeping with her. If she does drugs what other high risk behaviour is she involved in? I wouldn't touch him with a barge pole. There's plenty more people out there then clinging onto teenage crushes with a divorced man who takes in homeless women. She must be vulnerable and some people play on that
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A
female
reader, Honeypie + ♥, writes (21 November 2019):
 Definitely a red flag.
He is creating a scenario where HE is the "white knight" and took in a homeless woman out of the goodness of his heart, magically it turned into a intimate relationship and she stayed but caused problems for 3!!!! years and he did nothing?
I'm sorry, he might have been someone you had a thing for back in high-school but you are TOTALLY fooling yourself if you think he is STILL "that" guy from back then.
He also left you a voice mail that basically told you nothing of what really is going on between them other than she is a woman, for what purpose? To clean things up? Because it didn't, it's "clear as mud".
OP, I get that you had hoped something could happen romantically with you and this "blast from the past" but right now? He isn't who you think he is. He is now 15 years (at least) older and have a whole lot more baggage than back then.
Secondly, you have NO way of really know who she is and what their actual relationship is.
Thirdly, you haven no idea if HE is also into drugs, if he is the one who has been in trouble with the law, whether HE was the cause o those domestic issues etc. etc. YOU don't know. And he SURELY wouldn't tell you.
All you know is that HE is TRYING to paint a "pretty picture" for you.
You two talked for a week and all was dandy, but when it came down to perhaps meeting up he suddenly come up with this story of him being this VERY compassionate Hero and she being a damsel in distress that HE rescued and kept around. FOR 3 years. Who does that?
If you want to meet up in hopes of rekindle High-school feelings I think what you are going to get is a LOT of heart ache and drama.
Don't be naive.
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A
female
reader, anonymous, writes (21 November 2019): I don't quite believe his back story. I have found in my life that when someone tells you a story in which they are painted as being altruistic and kind and having no part in approaching someone or making something happen, that it's not true.
I don't think I'm explaining myself very well but when a man tells someone that he was just standing around minding his own business and a woman approached him, I'd be wary. It may well be true, BUT when it is followed with 'I asked her to stay the night because I am giving back to society', then I would start to get more wary.
AGAIN, it MIGHT be true. But it doesn't sound it, to me. He is painting himself as having no part in meeting her or instigating anything and also painting himself as being incredibly kind and going way beyond the call of duty by asking a confused homeless woman to stay at your home.
If there were no feelings and his story was true and he WAS kind enough to do this, then I suspect that he would have found her a hostel or SOMETHING. I find it unlikely that he would let a homeless person who he does not know and therefore does not know how she would behave in his home, especially if she was confused, stay at his home.
This back story being somewhat embellished, is now further confirmed by the fact that he DOES/DID have an attraction for her otherwise they wouldn't have had sex. And he wouldn't be so concerned for her welfare.
I don't know what the situation is now, all I can say to you is that I don't believe his back story. He is leaving quite a large chunk out I would suspect.
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