Need advice on what to do with a close friend (long read, sorry in advance)

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First a bit of a background. I've known this guy since 04, considered him a brother. We partied together, had great times, bad times. Always had each others backs and all that. Time passed by and we both settled down with our girlfriends (in my case i got married). While he still played the field and was in and out of relationships. some solid ones and some not so great.

We still kept contact through the years, he lives close by, So once in a while we would hang out.

So fast forward to the present... i haven't actually seen him in 2 yrs. We still call and text, keep in touch through facebook.

Alright, here's the situation (gonna try to break it up as much as possible to avoid wall 'o texts. apologize in advance for misspelled words. ):

I get a text from him a few days ago asking right out if he can borrow money. Now, he always starts his texts with "hey man how's it going", "how you been". Before asking for a favor of any kind (but this marks the first time he has asked me for money).
I respond with a hey man, hope you're doing ok. Sure thing i can let you borrow a few hundred bucks. he responds with awesome man, can you download this app and transfer the money to my account. I hesitate because i have used this before and ended up with an error from the transaction and lost out on the money (not much, but still). So i tell him that. and say that i actually have the money in hand, and i can meet him anywhere to hand it over.

And this is where things start taking a turn for the weird:

He responds with those apps are perfectly safe, etc. I say, i understand , but i rather just meet you for the money. I call him and he doesn't answer. He texts back that he can't talk because he's at work. I say ok cool. When you get a chance, call me then. He then says i didn't want to tell you this, but my son is addicted to meth, he stole my wallet and my account is negative. and it hurts my pride to ask you for money.
I tell him i'm very sorry to hear that (but his texts are becoming a bit pushy for me to download that transfer app). And at that point im thinking his son could be the one to reach out to his friends on his phone (i'm thinking he may have stole his phone too). I tell him that i haven't seen him in such a long time, and it would be nice to see him and talk for a bit, and of course give him the money that he needs.

Honestly i just want to make sure it's him at this point.

So he then texts, sorry man I have to drive to my ex's house, my ex called me (he had kids with a woman many many yrs ago, they share custody) My kid is coming off a high and he's turning violent and i gotta go calm him down.

How could he not speak to me, but can answer his ex's call (i get they have a kid and he's in trouble so i let it go). He then reiterates he really needs the money and if i can download the app and send it.

I start getting very skeptic about this, because this doesn't sound like the friend i have known all these yrs. Sooo, i go and contact his sister on facebook and ask her how she's doing, before i lay down the situation. I ask her if she knows if his phone was stolen, because of his weird texts. her response read like she hasn't spoke to him in a bit. She asked what the favor is about, and i tell her he asked me not to say anything. But i know they've been so close the whole time ive known them. And i still have my suspicions that it might be his kid.

*During the conversation i have with her, he actually calls me*

He says he's on his way to his ex's house to calm him down and he's actually gonna drive him down to austin texas to a rehab facility. I say ok, If you still need the money i can meet you off an exit from the highway you're gonna be driving south on. Since that Hwy passes close to where i live... He says, he's on a timeline and he also sounds very agitated. He says he doesn't know how long he's gonna be at his ex's because the son has locked himself in his room. I tell him ok. just let me know, if i have to drive up there to deliver the money, then so be it. * Call is over with him*

His sister tells me he that he's not doing well emotionally. He had broken up with his girlfriend turned fiancée of 3+yrs (i knew this because he called me when it happened) But she also said he lost his job (this i didn't know) and that she actually lend him money (his sister). He has a job now, so she said she doesn't understand why he needs money from me.

I really didn't wanna contact her guys, but this was very unlike him and i was legitimately worried about him. Specially the way he sounded on the phone. I then go ahead and tell her what he's been telling me that day. And she calls me to tell me what i didn't wanna hear... Yes, the son has had drug trouble, but he's already in his rehab facility down in Austin Tx (3 weeks ago). She says she has no idea why he would lie. I ask her then if she thinks he may be on drugs. But she says no way, because he knows better. She asks that i keep her updated if i want to, but she also advices me that while she can't tell me whether or not i should lend him the money. She thinks that i shouldn't. We end the the call at this time. His sister also told me that he's been on and off with this chick he just broke up with and that she's no good for him.

So i have a bit to think about, and the whole thing is... If i needed money and someone is offering to lend it to me and all i have to do is meet them, im gonna do it.

I just don't understand why he lied about the situation with his kid. He wasn't on his way to calm him down, and he definitely wasn't taking him down to rehab. So i think he's actually on drugs. About 4yrs ago, before he got with the girl he just broke up with, he was actually on cocaine (he told me this). And i talked to him and straightened him out.

And the fact that he was sooo hesitant to meet up with me for the money makes me think he doesn't want to see me because i'll be able to tell he's on something.

I love this guy like a brother, but at the same time i don't want to enable him. I have no idea what to do guys. he actually reached out to me yesterday. And i told him i'll still meet him if he needs the money. But he stressed the app again.

if you're still reading. i really appreciate it guys. I rarely post personal stuff. But i really need help on this one.

Thanks for taking the time to read this.
 
He shouldnt have asked you to download the app, that was the wrong thing to do
 
I'm sorry that your friend is going through a rough patch right now. Do NOT send money to him via that app. It just sounds too shady and if sounds shady....

If he really wants the money, he'll agree to meet, if not, then something in the milk ain't clean.

Be careful and keep the sister in the loop. Sounds like she knows what's up.

I'm praying for you bro.
 
Coming from someone who's been a piece of shit who didn't learn his lesson, don't give him any money.

You'd only be enabling his bullshit behavior and not actually helping him at all.
 
He can fuck off. He's shitting on what's left of your friendship.

Don't download some sketchy fucking app. If he is in serious need of money he can meet you face to face and tell you like a man. Him lying to you speaks to his intentions.
 
any chance of cliffs?
I mean i could sherbro. but i'm also having problems of my own ( besides the ones with my friend). I'm drinking a bit right now. I may post a different thread to talk about those, But i don't think it's that long of a read bud.
 
If you want to help him whether you think the problem is with him or his son, I think you should tell him that you want to meet up with him, no matter what the circumstances, you're not going to negatively judge him or look down on him, you understand things don't always go the way we plan or hope, you just want what's best for him, and you see him as a brother. If he doesn't go for that then he might not be open to bringing you into his situation which I think may answer you're questions. I know money problems can be hard to deal with but is a few hundred dollars really going to make or break somebody? You would know more about that with regards to him than I would.
 
Yeah, you're being a good friemd here. You're treating him like a brother, but he isn't doing the same. It sounds like drugs, especially since you said he had dabbled with cocaine before...but , maybe something else is going on?

For me, I would have also refused to download the app, regardless of why he needs the money. You guys don't live far away, and you even offered to drive to him, so there's no excuse.
I would probably try to force the meeting and get the real story out of him. If this is a drug thing , and i felt i wasn't getting the real story out of him, i think I'd ask his sister if it was cool if i let him know that i talked to her already, and that he needs to be truthful if he wants the money.

I have a few friends that are like brothers to me as well, and if they're doing something stupid or dangerous, im going to set them straight, as a brother should. He should trust you with the truth if he's going to ask you for money, and if you guys are that close.
 
It wasn't right for your friend to stab that midget, I don't care he said about his grandma.
 
Straight up tell him you talked to his sister(because you were concerned for his well-being) and ask him to give you the real story. Don't transfer money via an app and likely don't give him any anyway(depending on real story).

Also if you do give him cash don't miss it as there is a high chance you won't see it again.
 
Sometimes caring about someone, and not trusting them is the same thing.
 
Call him out on it and take it from there. You tell him that you were concerned and reached out to his sister. He could just be bad at managing money or on drugs. But that's not the point. You need to call him out on that bullshit.
 
If you want to help him whether you think the problem is with him or his son, I think you should tell him that you want to meet up with him, no matter what the circumstances, you're not going to negatively judge him or look down on him, you understand things don't always go the way we plan or hope, you just want what's best for him, and you see him as a brother. If he doesn't go for that then he might not be open to bringing you into his situation which I think may answer you're questions. I know money problems can be hard to deal with but is a few hundred dollars really going to make or break somebody? You would know more about that with regards to him than I would.
i just don't want to enable him. Honestly the money isn't a problem. But it's the principle of the thing, he lied to me. And we have always been honest with each other. I have had his back when he's been though very rough times. So him lying doesn't fly with me. I'm a very loyal friend man, all i ask for is honesty and loyalty.

i understand it's probably embarrassing/humiliating to go what he's going through. But i won't judge him. He's a brother to me. So there's no need to BS
 
i just don't want to enable him. Honestly the money isn't a problem. But it's the principle of the thing, he lied to me. And we have always been honest with each other. I have had his back when he's been though very rough times. So him lying doesn't fly with me. I'm a very loyal friend man, all i ask for is honesty and loyalty.

i understand it's probably embarrassing/humiliating to go what he's going through. But i won't judge him. He's a brother to me. So there's no need to BS

Yeah, what I'm saying is you need to get him to understand that. Just the way you explained it in your response to me. I wish you the best.
 
First a bit of a background. I've known this guy since 04, considered him a brother. We partied together, had great times, bad times. Always had each others backs and all that. Time passed by and we both settled down with our girlfriends (in my case i got married). While he still played the field and was in and out of relationships. some solid ones and some not so great.

We still kept contact through the years, he lives close by, So once in a while we would hang out.

So fast forward to the present... i haven't actually seen him in 2 yrs. We still call and text, keep in touch through facebook.

Alright, here's the situation (gonna try to break it up as much as possible to avoid wall 'o texts. apologize in advance for misspelled words. ):

I get a text from him a few days ago asking right out if he can borrow money. Now, he always starts his texts with "hey man how's it going", "how you been". Before asking for a favor of any kind (but this marks the first time he has asked me for money).
I respond with a hey man, hope you're doing ok. Sure thing i can let you borrow a few hundred bucks. he responds with awesome man, can you download this app and transfer the money to my account. I hesitate because i have used this before and ended up with an error from the transaction and lost out on the money (not much, but still). So i tell him that. and say that i actually have the money in hand, and i can meet him anywhere to hand it over.

And this is where things start taking a turn for the weird:

He responds with those apps are perfectly safe, etc. I say, i understand , but i rather just meet you for the money. I call him and he doesn't answer. He texts back that he can't talk because he's at work. I say ok cool. When you get a chance, call me then. He then says i didn't want to tell you this, but my son is addicted to meth, he stole my wallet and my account is negative. and it hurts my pride to ask you for money.
I tell him i'm very sorry to hear that (but his texts are becoming a bit pushy for me to download that transfer app). And at that point im thinking his son could be the one to reach out to his friends on his phone (i'm thinking he may have stole his phone too). I tell him that i haven't seen him in such a long time, and it would be nice to see him and talk for a bit, and of course give him the money that he needs.

Honestly i just want to make sure it's him at this point.

So he then texts, sorry man I have to drive to my ex's house, my ex called me (he had kids with a woman many many yrs ago, they share custody) My kid is coming off a high and he's turning violent and i gotta go calm him down.

How could he not speak to me, but can answer his ex's call (i get they have a kid and he's in trouble so i let it go). He then reiterates he really needs the money and if i can download the app and send it.

I start getting very skeptic about this, because this doesn't sound like the friend i have known all these yrs. Sooo, i go and contact his sister on facebook and ask her how she's doing, before i lay down the situation. I ask her if she knows if his phone was stolen, because of his weird texts. her response read like she hasn't spoke to him in a bit. She asked what the favor is about, and i tell her he asked me not to say anything. But i know they've been so close the whole time ive known them. And i still have my suspicions that it might be his kid.

*During the conversation i have with her, he actually calls me*

He says he's on his way to his ex's house to calm him down and he's actually gonna drive him down to austin texas to a rehab facility. I say ok, If you still need the money i can meet you off an exit from the highway you're gonna be driving south on. Since that Hwy passes close to where i live... He says, he's on a timeline and he also sounds very agitated. He says he doesn't know how long he's gonna be at his ex's because the son has locked himself in his room. I tell him ok. just let me know, if i have to drive up there to deliver the money, then so be it. * Call is over with him*

His sister tells me he that he's not doing well emotionally. He had broken up with his girlfriend turned fiancée of 3+yrs (i knew this because he called me when it happened) But she also said he lost his job (this i didn't know) and that she actually lend him money (his sister). He has a job now, so she said she doesn't understand why he needs money from me.

I really didn't wanna contact her guys, but this was very unlike him and i was legitimately worried about him. Specially the way he sounded on the phone. I then go ahead and tell her what he's been telling me that day. And she calls me to tell me what i didn't wanna hear... Yes, the son has had drug trouble, but he's already in his rehab facility down in Austin Tx (3 weeks ago). She says she has no idea why he would lie. I ask her then if she thinks he may be on drugs. But she says no way, because he knows better. She asks that i keep her updated if i want to, but she also advices me that while she can't tell me whether or not i should lend him the money. She thinks that i shouldn't. We end the the call at this time. His sister also told me that he's been on and off with this chick he just broke up with and that she's no good for him.

So i have a bit to think about, and the whole thing is... If i needed money and someone is offering to lend it to me and all i have to do is meet them, im gonna do it.

I just don't understand why he lied about the situation with his kid. He wasn't on his way to calm him down, and he definitely wasn't taking him down to rehab. So i think he's actually on drugs. About 4yrs ago, before he got with the girl he just broke up with, he was actually on cocaine (he told me this). And i talked to him and straightened him out.

And the fact that he was sooo hesitant to meet up with me for the money makes me think he doesn't want to see me because i'll be able to tell he's on something.

I love this guy like a brother, but at the same time i don't want to enable him. I have no idea what to do guys. he actually reached out to me yesterday. And i told him i'll still meet him if he needs the money. But he stressed the app again.

if you're still reading. i really appreciate it guys. I rarely post personal stuff. But i really need help on this one.

Thanks for taking the time to read this.

Tough situation. I wouldn't give him the money, it sounds like you won't get it back and he'd use it to buy drugs.

Go with your gut.
 
Talk to him face to face, find out why he lied, then determine if you still want to lend the money. Doesn't sound like a good idea. He's probably on drugs.
 
I didn't read thoroughly. If this was a movie I'd think the son was trying to trick you into wiring him money. Starring Edward Furlong.
 
You sound like a very conscientious person so i would say - for your own peace of mind - don't feel guilty for talking with your friend's sister - you didn't do that to snitch, gossip or get out of obligations, you talked to her to get a handle on the sitation with the intent of actually doing what's best for your friend/friendship in the long term. And to get information your friend should have provided you with in the first place.

I think the best thing you can do is continue what you are already doing: Getting a handle on the reality of the situation and letting your friend know that you are there for him, to talk with and to meet.

Be a friend, but not a moneylender/enabler.

Doesn't really matter if he's on drugs, needs the money to pay off other debts or plans on splashing out on something crazy to impress his on again off again girl. He has lied to you and he is trying to take advantage of your friendship. Like other's have said, trust your gut feeling, and stick to your principles, you will be able to help him much more in the long run by being true to yourself and to him.

But to be honest, from my point of view, him lying to you is a bad omen and a sign that he is already in a situation that probably requires help outside of what you can provide.

Best wishes.
 
I don't think assuming the worst, or 'going with your gut' is the right way to go here.
If this is a guy that's like your brother, and this behavior is out of the ordinary for him, I'd give him the benefit of the doubt.
We're all assuming it's drugs, but it could just be a really embarrassing or difficult to explain situation that he doesn't want to go into.
Just because he lied, that doesn't mean he has some nefarious thing going on.
 
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