Sister Making Imprudent Financial and Relationship Decisions

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One of my sisters (early 20s) has been dating a guy fairly seriously for the past year or so. He’s the same age as she is, but is already divorced with a child in elementary school (high school girlfriend got pregnant, he “did the right thing,” she ended up being crazy, etc.) I have never met him, but parents assure me that he “is a nice guy paying for some dumb mistakes,” although they aren’t thrilled that my sister is dating him because there’s a LOT of baggage there (besides ordinary blended family issues, there’s substance abuse as well as suspected abuse/neglect by the ex, unfortunately all unproven, and this poor kid has a lot of issues.) They don’t say anything, though, because “your sister is going to do what she wants to do” (true) and “anyway, she’s an adult.” (Also true, but she lives at home rent-free, though she does have a job.)

However…

A recent phone conversation with my sister revealed that this guy has some serious financial problems. He recently went through bankruptcy, and my sister is apparently planning on paying for him to go back to school. If they were married, then, OK, maybe, but they are not even engaged. This sends red flags flying all over the place for me. Sis wants to be a SAHM. She has her own student loans to pay off. I am worried that at best she’s tying herself to a well-intentioned not bright guy and at worst a manipulator who’s out to use her. She’s been in two other serious relationships: one guy was an alcoholic who hit her, the other guy also hit her, and ended up committing suicide. She has a tendency to want to rescue people.

So far, I have just warned her to be cautious about her money and work toward being secure before getting married. She was dismissive, which is her right. I think she might put more stock in my mother’s opinion, but my mother tends to never say anything because she hates confrontation. But I don’t know if my mom knows about the money. My sister did not tell me it was a secret of any kind (she was in a room with other people when talking to me on the phone), and while I know I can’t stop her from doing anything, she’s tried to rescue two guys before and nobody said anything to her (I was across the country and didn’t know, Mom and Dad knew something was up but “didn’t want to pry.”)

I really don’t know if and how to help her.(Emphasis on the " if," too - I do not want to tattle, I pray for her - I just feel like if somebody saying something is going to help, then I want to make that happen. A lot of teens and young adults say they want parents to butt out, but my parents take that to such an extreme that it can be interpreted as uncaring.)
 
It sounds like your parents won’t say anything, even if you ask them to.

As for whether you should say anything anyway - well, each family has it’s own dynamics that outsiders often don’t understand. In short, only you can judge what the best thing to do is, whether your sister would resent your talking to your parents and involving them, and whether there is really any way to help her in this situation. Maybe all you can really do is be there in case she needs to talk to someone and for when everything turns sour. And pray of course.
 
Fiirst, I would have a talk with your parents about how this can affect your sisters future. If
your sister gives him money- for a class or two,at a community college it is not so bad-but still bad enough probabaly aound 500.00 or so to lose.

He may also ask her to co- sign a student loan and that can finacially ruin your sister when he does not pay the loan. Inform your parents about this possibility. If your sister is finacially dependent on your parents to provide free room and board, this shows that she does not really have a grasp of how to manage finaces for herself let alone support another persons education.

I would do this to protect your sister and motivate your parents to talk to her. If you paint a very bad scenario-they may step up and advise her.

They should tell your sister in a kind way to be smart with her money and try and get her to make this guy postpone school until she saves more money. She will buy time this way and he may go away.

If nothing works, you did all you could.
 
One of my sisters (early 20s) has been dating a guy fairly seriously for the past year or so. He’s the same age as she is, but is already divorced with a child in elementary school (high school girlfriend got pregnant, he “did the right thing,” she ended up being crazy, etc.) I have never met him, but parents assure me that he “is a nice guy paying for some dumb mistakes,” although they aren’t thrilled that my sister is dating him because there’s a LOT of baggage there (besides ordinary blended family issues, there’s substance abuse as well as suspected abuse/neglect by the ex, unfortunately all unproven, and this poor kid has a lot of issues.) They don’t say anything, though, because “your sister is going to do what she wants to do” (true) and “anyway, she’s an adult.” (Also true, but she lives at home rent-free, though she does have a job.)

However…

A recent phone conversation with my sister revealed that this guy has some serious financial problems. He recently went through bankruptcy, and my sister is apparently planning on paying for him to go back to school. If they were married, then, OK, maybe, but they are not even engaged. This sends red flags flying all over the place for me. Sis wants to be a SAHM. She has her own student loans to pay off. I am worried that at best she’s tying herself to a well-intentioned not bright guy and at worst a manipulator who’s out to use her. She’s been in two other serious relationships: one guy was an alcoholic who hit her, the other guy also hit her, and ended up committing suicide. She has a tendency to want to rescue people.

So far, I have just warned her to be cautious about her money and work toward being secure before getting married. She was dismissive, which is her right. I think she might put more stock in my mother’s opinion, but my mother tends to never say anything because she hates confrontation. But I don’t know if my mom knows about the money. My sister did not tell me it was a secret of any kind (she was in a room with other people when talking to me on the phone), and while I know I can’t stop her from doing anything, she’s tried to rescue two guys before and nobody said anything to her (I was across the country and didn’t know, Mom and Dad knew something was up but “didn’t want to pry.”)

I really don’t know if and how to help her.(Emphasis on the " if," too - I do not want to tattle, I pray for her - I just feel like if somebody saying something is going to help, then I want to make that happen. A lot of teens and young adults say they want parents to butt out, but my parents take that to such an extreme that it can be interpreted as uncaring.)
I think this has two ends: your parents and your sister.

With your sister, I think I’d ask her (in a quiet moment) how this is going to work. How is it that she going to pay off her loans, send him to school and be an SAHM? To my ear, that sounds like she’s going to be working indefinitely. The SAHM route and the send-future-husband-to-college route are two different routes, not the same thing.

You can also tell her about your experiences of paying on your student loans as a SAHM–feel free to lay it on thick talking about your lifestyle. You can go ahead and criticize past you to your sister and point out to her where you think you went wrong and how much struggle is ahead of her, even if everything goes exactly to plan.

I’m sure she doesn’t really understand yet what the implications are of her plan because she hasn’t had a live-fire exercise yet. Of course, if it’s just a community college certificate, then no biggie, but one concern that comes to mind is that your sister’s boyfriend is not four year college material, so there’s a very large probability that he is going to do a little college and then bail on it (and that would be consistent with his life trajectory so far). So it might be a good idea (if sister is still listening at that point) to encourage them to have him start at the community college level before trying a four-year college. If he can’t hack community college (and I have my doubts from reading his story), he won’t be able to hack a four year degree. If he can manage CC, there’s a good chance he can cope with a four year college.

Your parents are the other end of the problem. You can tell them what her plan is and that you’re worried, because you don’t think sister understands how hard it’s going to be. One possibility is to encourage your parents to start charging sister rent and bank the money for her (or just make her saving the amount). Figure out how much more a month her new lifestyle is supposed to cost, and then start banking that every month. One possibility is that as sis’s savings grow and she cuts down her lifestyle, she’s going to become less and less enthusiastic about the prospect of carrying her boyfriend. (There’s also unfortunately the possibility that she just moves her spending onto credit.)

But I don’t know that it will be possible to persuade your parents to do the forced savings plan. But it would be a very good thing for them to do. (That’s what I hope to do with any of my kids that live at home for college and young adult years–I’d like college students to save $100-$200 a month and graduates to save around $300 a month. I don’t think that’s unreasonable, especially for graduates.)
 
As a parent to adult children, I say to cut your parents some slack. They are in a tough spot. They can give gentle loving advice (that you may not be privy to since you are not in the house) or they can alienate their adult daughter and risk rushing her into a marriage that may not be ideal. More than likely, your parents are keeping their door open for their child. When a parent doesn’t like a girlfriend or boyfriend, that is when they need to actually show more love to the new potential family member.

Besides, your sister is an adult. If you feel the need to give her advice, do so. But don’t lay it at the feet of your parents. They have another role to play.
 
It’s not your circus and they’re not your monkeys. Any advice that you give your sister will not be appreciated or listened to and will only serve to alienate her. I can tell you the only thing that I do for members in my family who make really poor financial decisions is put aside money to keep them off the streets. And the money is only for keeping them off the streets - it isn’t to keep them in their house or provide them with a vehicle. It is “I’m living in a van down by the river” type of money.
 
Thank you for the replies.

Unfortunately, after reading them and considering some more, I think it’s unlikely that a train wreck will be avoided. My parents are the definition of “emotionally unavailable,” and there’s zero indication that has changed since I left home -most of the evidence points the other way.

Sis definitely has very poor understanding of finances. None of her income goes toward necessities (except minimum debt payments). She does have a lot left over every month, and she puts that in savings. She doesn’t know how much is in there, nor does she know how the interest rate compares. I told her to check because the loans are probably higher, in which case they definitely need to be paid back first. Even if she started today and didn’t touch her savings she could be debt free in a year.

She’s convinced boyfriend is going to leave school and immediately have a 6 figure income. Average starting for his desired field is around 100k, but I definitely have my doubts that he gets there. One positive is that he’s ex military and qualifies for benefits from the GI bill. But she was very sketchy on the details, which makes me nervous. I tried to be very delicate and not judgey about the concerns I had, so maybe she’ll consider them. But I have a feeling that’s the best I’m going to do. 😦
 
Thank you for the replies.

Unfortunately, after reading them and considering some more, I think it’s unlikely that a train wreck will be avoided. My parents are the definition of “emotionally unavailable,” and there’s zero indication that has changed since I left home -most of the evidence points the other way.

Sis definitely has very poor understanding of finances. None of her income goes toward necessities (except minimum debt payments). She does have a lot left over every month, and she puts that in savings. She doesn’t know how much is in there, nor does she know how the interest rate compares. I told her to check because the loans are probably higher, in which case they definitely need to be paid back first. Even if she started today and didn’t touch her savings she could be debt free in a year.

She’s convinced boyfriend is going to leave school and immediately have a 6 figure income. Average starting for his desired field is around 100k, but I definitely have my doubts that he gets there. One positive is that he’s ex military and qualifies for benefits from the GI bill. But she was very sketchy on the details, which makes me nervous. I tried to be very delicate and not judgey about the concerns I had, so maybe she’ll consider them. But I have a feeling that’s the best I’m going to do. 😦
Wait until she brings it up next.

It’s good that your sister has actual savings but pretty aggravating that she could have it all paid off in a year but isn’t. I suppose it all sounds very unreal without having actual expenses to take care of (especially family expenses). But, then, by the time you have real expenses, it’s too late…

If he has GI Bill benefits, why does she have any financial role to play in keeping him afloat? (Of course, it might be a long enough program that it wouldn’t apply, but that means that her whole SAHM plan gets pushed out that much longer, too.)

I share your concerns about the $100k a year. Those things do not grow on trees, especially for new graduates, and the ones that do pay that are very intellectually demanding, not to mention selective. (I suppose it’s something like a physicians assistant?)

I guess it all boils down to your sister probably wanting more emotional engagement than she grew up with, and being able to find it with guys who need her badly.
 
…A recent phone conversation with my sister revealed that this guy has some serious financial problems. He recently went through bankruptcy, and my sister is apparently planning on paying for him to go back to school. If they were married, then, OK, maybe, but they are not even engaged. This sends red flags flying all over the place for me. Sis wants to be a SAHM. She has her own student loans to pay off. I am worried that at best she’s tying herself to a well-intentioned not bright guy and at worst a manipulator who’s out to use her. She’s been in two other serious relationships: one guy was an alcoholic who hit her, the other guy also hit her, and ended up committing suicide. She has a tendency to want to rescue people.

So far, I have just warned her to be cautious about her money and work toward being secure before getting married. She was dismissive. … she’s tried to rescue two guys before …I really don’t know if and how to help her.(Emphasis on the " if," too - I do not want to tattle, I pray for her - I just feel like if somebody saying something is going to help, then I want to make that happen. A lot of teens and young adults say they want parents to butt out, but my parents take that to such an extreme that it can be interpreted as uncaring.)
This sends red flags to me as well. It sounds like your sister is trying to pay for her own dowry! Dowry systems are notoriously problematic.

Apart from the obvious financial concerns of her giving away money for someone else’s education when she already owes money for her education, the dating history reeks of someone who feels better about herself by hanging around with “fix-up projects”. She looks good by comparison to the people she’s dating, and if she manages to fix-up her boyfriends life, then it makes her look even better in her mind. I have that Disney song, “He’s a bit of a fixer upper” running through my head now. More Disney–she saw his potential–he’s a “diamond in the rough”–just waiting to be polished-up by someone like her.

This looks a lot like a female version of “knight in shining armor” syndrome when dating turns into trying to “rescue” someone in distress. Charity and help for the less fortunate shouldn’t be confused with courtship. That creates an unbalanced relationship, where one party “owes” the other party for rescuing them. It sets up weird roles for their future together: one party feels she/he is the one in power/control and the other one is the one in distress/need. She gets to be the “responsible one” and he gets to be the “needy one”. While I see your worries that your sister may be taken advantage of, I also see worries that *she *may be the one taking advantage of him, trying to make him feel somehow “obliged” to her.

She doesn’t want you to help her; she wants to be the one who “helps someone in need”. What she seems to be missing out on is the fact that who we date and marry reflects how we see ourselves. We pick someone who either is like us or who balances us out in some regard or who is somehow familiar to us–or all of the above. It sounds like she’s selling herself short in order to buy a husband. If she thinks he’s the kind of man who can be bought, then that doesn’t speak well of what she really thinks of him or herself.
 
It makes me nervous when a person describes their ex as “crazy.” Sometimes it’s true; sometimes the truth is complicated, and sometimes the person talking is the type to believe everything is the other person’s fault.

These questions aren’t meant to be answered publicly but are things I thought about while reading this.

If she is crazy and abusive/neglectful, why isn’t he trying harder to get custody? If there’s no evidence that can be brought up in court, what is he seeing? Is he really advocating for his child or is he complaining about his ex’s stability while really not doing much himself to step up to the plate as a father. Also, is he getting the benefit of the doubt as making “dumb mistakes” while the child’s mother is viewed as the bad person in this?

I don’t know the truth but it could be that the child’s mother is a great person and doing the best she can at parenting, and his accusations are untrue. Or maybe he’s right and there is a bias in favor of the mother, and he’s unable or unwilling to work with lawyers and pursue the detailed documentation that would be required for any changes. Or maybe she is severely mentally ill and he has abandoned his child by leaving the care partly/mostly up to the mother.

Or something else, but is he letting things slide as a parent with a child who is having trouble? I’d be concerned. Your sister may or may not listen though.

If the ex is crazy and/or manipulative, your sister may have to deal with harassment or drama b/c the ex may want to control the situation. Is the child in therapy or getting other help?
 
Thank you for the replies.

Unfortunately, after reading them and considering some more, I think it’s unlikely that a train wreck will be avoided. My parents are the definition of “emotionally unavailable,” and there’s zero indication that has changed since I left home -most of the evidence points the other way.

Sis definitely has very poor understanding of finances. None of her income goes toward necessities (except minimum debt payments). She does have a lot left over every month, and she puts that in savings. She doesn’t know how much is in there, nor does she know how the interest rate compares. I told her to check because the loans are probably higher, in which case they definitely need to be paid back first. Even if she started today and didn’t touch her savings she could be debt free in a year.

She’s convinced boyfriend is going to leave school and immediately have a 6 figure income. Average starting for his desired field is around 100k, but I definitely have my doubts that he gets there. One positive is that he’s ex military and qualifies for benefits from the GI bill. But she was very sketchy on the details, which makes me nervous. I tried to be very delicate and not judgey about the concerns I had, so maybe she’ll consider them. But I have a feeling that’s the best I’m going to do. 😦
Prayer prevents a lot of train wrecks. The Good Lord has been known to look out for fools and little children.

As for your sister, give advice sparingly and respectfully when you are asked. Express a positive belief in your sister’s ability to make her own decisions. When you are given to know that your advice is not wanted, keep it to yourself.

If there is a train wreck, never say, “I told you so.” You could not give a better gift, and “the measure you measure with will be measured back to you.” Mercy will always be its own reward, in the long run.
 
Prayer prevents a lot of train wrecks. The Good Lord has been known to look out for fools and little children.

As for your sister, give advice sparingly and respectfully when you are asked. Express a positive belief in your sister’s ability to make her own decisions. When you are given to know that your advice is not wanted, keep it to yourself.

If there is a train wreck, never say, “I told you so.” You could not give a better gift, and “the measure you measure with will be measured back to you.” Mercy will always be its own reward, in the long run.
I like this answer. It always helps to be reminded of the benefits of prayer 🙂 I agree with not saying I told you so as well.
 
It makes me nervous when a person describes their ex as “crazy.” Sometimes it’s true; sometimes the truth is complicated, and sometimes the person talking is the type to believe everything is the other person’s fault.

These questions aren’t meant to be answered publicly but are things I thought about while reading this.

If she is crazy and abusive/neglectful, why isn’t he trying harder to get custody? If there’s no evidence that can be brought up in court, what is he seeing? Is he really advocating for his child or is he complaining about his ex’s stability while really not doing much himself to step up to the plate as a father. Also, is he getting the benefit of the doubt as making “dumb mistakes” while the child’s mother is viewed as the bad person in this?

I don’t know the truth but it could be that the child’s mother is a great person and doing the best she can at parenting, and his accusations are untrue. Or maybe he’s right and there is a bias in favor of the mother, and he’s unable or unwilling to work with lawyers and pursue the detailed documentation that would be required for any changes. Or maybe she is severely mentally ill and he has abandoned his child by leaving the care partly/mostly up to the mother.

Or something else, but is he letting things slide as a parent with a child who is having trouble? I’d be concerned. Your sister may or may not listen though.

If the ex is crazy and/or manipulative, your sister may have to deal with harassment or drama b/c the ex may want to control the situation. Is the child in therapy or getting other help?
Those are all fair questions–especially the bit about being aware of people who talk about “crazy” exes.

I was thinking that the most charitable explanations of his bankruptcy was that he may have gotten in over his head with legal bills trying to obtain custody or visitation.

The less charitable explanation is that he had a good, steady job, but that he got sucked into the young soldier lifestyle of live-for-today with EZ payments on everything and it got out of hand, especially once he left the military.

But the reality might be a combination of those two.
 
Those are all fair questions–especially the bit about being aware of people who talk about “crazy” exes.

I was thinking that the most charitable explanations of his bankruptcy was that he may have gotten in over his head with legal bills trying to obtain custody or visitation.

The less charitable explanation is that he had a good, steady job, but that he got sucked into the young soldier lifestyle of live-for-today with EZ payments on everything and it got out of hand, especially once he left the military.

But the reality might be a combination of those two.
That’s true; maybe he has tried everything to get custody or better visitation and it didn’t work. I guess I would want to know about finances between him and his ex. Assuming he is paying child support, is that going smoothly? Are they working together at co-parenting reasonably well or is that really problematic. It sounds like there are issues there from what you said. Your sister may be placed in a stepmother type role, whether or not they ever marry, with a child who is troubled/special needs.

The more I think about it, the more I agree that prayer is great advice and realizing there may not be much you can say b/c she can’t hear it at this point.
 
Xantippe, gardenswithkids, and silver moon, those are very similar to the concerns I have been having. For my part, I feel like there’s a lot that doesn’t add up in this situation, especially regarding the legal issues. My thought is that the boyfriend either has very poor legal representation, or is misleading my sister about what’s going on. I think she actually went to the hearing where the mother was awarded majority custody, and references were made to neglect by the mother that needed to be corrected ASAP (the boy has a chronic health condition - it doesn’t negatively impact his quality of life when it is controlled, but apparently she was neglecting to get him to the doctor or get him his medications). Why on earth a judge would award a woman custody in that scenario is beyond me.

Unfortunately (IMO) for both my sister and this little boy, she’s already playing stepmom. 😦 In addition to the craving emotional attention, my sister really wants to be married and have children. She talked marriage very early with the other two boyfriends, too. I do have to give my mom credit for warning my sister that even if this little boy is in their future home every other weekend, that’s enough to have a huge impact on her hypothetical children. (He shows signs of being emotionally disturbed as well - and if life with mom is as bad as she says, and if the custodial situation doesn’t change, it’s not like that’s going to get any better, and he won’t be a cute little kid much longer - he’ll be a big kid, then a teen.)

Thank you for the reminders to pray. I do, but I can get really wrapped up in the “but what do I do???” This was the first phone conversation I’d had with her in about a year - we send messages over Facebook and via text sometimes, but that’s not the same thing. We rarely get to visit.
 
…Why on earth a judge would award a woman custody in that scenario is beyond me…
Yet we all know that the justice system does not even work in ways we understand when we have the opportunity to sit through an entire trial. We may not see the wisdom in a decision, but that does not mean that some judge somewhere near us hasn’t made just such a decision.
 
Yet we all know that the justice system does not even work in ways we understand when we have the opportunity to sit through an entire trial. We may not see the wisdom in a decision, but that does not mean that some judge somewhere near us hasn’t made just such a decision.
That’s very true.

I have very little familiarity with family court, and apparently the state they live in is very “pro-mother.” By itself, it just sounds like something really unfortunate (though boyfriend can appeal and I think is or is planning to), but with everything else I have to admit I get suspicious.
 
Xantippe, gardenswithkids, and silver moon, those are very similar to the concerns I have been having. For my part, I feel like there’s a lot that doesn’t add up in this situation, especially regarding the legal issues. My thought is that the boyfriend either has very poor legal representation, or is misleading my sister about what’s going on. I think she actually went to the hearing where the mother was awarded majority custody, and references were made to neglect by the mother that needed to be corrected ASAP (the boy has a chronic health condition - it doesn’t negatively impact his quality of life when it is controlled, but apparently she was neglecting to get him to the doctor or get him his medications). Why on earth a judge would award a woman custody in that scenario is beyond me.

Unfortunately (IMO) for both my sister and this little boy, she’s already playing stepmom. 😦 In addition to the craving emotional attention, my sister really wants to be married and have children. She talked marriage very early with the other two boyfriends, too. I do have to give my mom credit for warning my sister that even if this little boy is in their future home every other weekend, that’s enough to have a huge impact on her hypothetical children. (He shows signs of being emotionally disturbed as well - and if life with mom is as bad as she says, and if the custodial situation doesn’t change, it’s not like that’s going to get any better, and he won’t be a cute little kid much longer - he’ll be a big kid, then a teen.)

Thank you for the reminders to pray. I do, but I can get really wrapped up in the “but what do I do???” This was the first phone conversation I’d had with her in about a year - we send messages over Facebook and via text sometimes, but that’s not the same thing. We rarely get to visit.
Oh dear.

Yeah, if that’s the degree of relationship you have, your influence is going to be limited.
 
You might try posting somewhere like this:

cafemom.com/group/114270

It is described as:
About Stepmom Central
Are you a stepmom? This is the place to share support, vent frustrations and find friendship with other stepmoms who understand your unique joys and challenges. The group is open to all perspectives – from birth moms to stepmoms and even moms who are step kids.
You may want to ask them about your sister. What worries me is both the potential burden on her and what might happen to the child if she is there for a while, say a couple of years, and then they break up. How will the child react if she is no longer in his life. And that’s a good point that since she wants her own biological children, this child will have an impact on them.

Best of luck to you. I can see that this is really hard.
 
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