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An interesting FWF question, I recently ended a relationship with a girlfriend (not wife) who owed me around $2,000.  When we returned each other's personal property, I asked when I could expect to see that money (expecting to be told I where I could stick that request) and the ex wrote a personal check on the spot. She told me she didn't have the money, but she had overdraft protection so I could at least get my money.

The ex owns a business which is teetering on the edge of insolvency and bankruptcy and she's going into her busiest season so it would be most beneficial for her to have that cash to invest in her business instead of paying off her significant other.  It would be nice to have the money, but I'm in good financial condition and the $2,000 won't make or break me. I've gotten the suggestion that I should try and work out some form of payment plan, but I foresee one of two results:

1. I don't get many (any?) payments when she wakes up and says "screw big man, what's he going to do about it?"
2. She winds up in bankruptcy in the next 6 months and my changes for repayment go from slim to none, as enforced by a judge.

The way I'm looking at it is the money was spent by her with the agreement it be returned, her financial issues are her problem.  On the other hand, it seems crappy to kick her when she's already down.

Thoughts?

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Your cashing a check someone wrote you can be considered petty theft?! Really?

gremln007 (Sep. 29, 2016 @ 8:12p) |

Play your cards right and you can get all that and 2k in your pocket.

scrouds (Sep. 29, 2016 @ 8:14p) |

What? OP was given a check in good faith. He has no intention to defraud another creditor...

alamo11 (Sep. 29, 2016 @ 8:24p) |

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Sounds like you still have a civil relationship, in which case I wouldn't feel good about myself cashing a check knowing she doesn't have the money. Tell her you appreciate her willingness to repay but you're going to hold off cashing the check and to please let you know when she has the money in her account. If you're worried she's going to flake on you, have her sign a promissory note. If she winds up in bankruptcy, be thankful you're doing well enough that you can afford to lose two grand and then forget about it.

Great question. Ultimately, do what you think is right. Both options fine depending on your personal values and what $2k means to you. I never lend to friends/family for this reason, give if I can, otherwise offer to help explore their financial options with them.

My guess is she wrote you a check to avoid loss of face/feelings in a hard situation for everyone. Perhaps a polite phone call of "hey, would $100/mo instead of me cashing this check help you with your busy season?" If you can't decide, let her. Also depends on on how amicable you want the split to be...

@doveroftke - Part of me says if this pushes her into bankruptcy, I'm just leaving her bank holding the bag from the overdrafted funds and they're far better equipped to handle debtors with inability to pay than I. However, I would like to remain civil and that's what is keeping me from standing in like at the bank right now.

jarfykk - $2,000 is my after tax income every two weeks and I live in a low cost of living area. It provides some additional nice seed capital for some real estate investments I'm considering and could repay some very low interest debt I have. On the other hand, if it puts her in a position where she's getting some really crappy loans or something to try and keep her head above water, me paying 2% interest seems a lot more reasonable than her paying 18% interest...on the other hand, that's not really my problem.

BigManonCampus said:    and she's going into her busiest season so it would be most beneficial for her to have that cash to invest in her business instead of paying off her significant other.

 

  Apparently she doesnt have the cash regardless, repaying you is requiring another crappy loan on top of whatever she needs for her business.  Frankly, the business is either going to survive or it isnt; at best your $2k only delays the inevitable by letting her dig an even deeper debt hole before failing, $2k debt is $2k debt regardless of who it is owed to.

She may be intentionally resolving "important" debts in anticipation of bankruptcy.  I'd deposit that check ASAP, because it can be clawed back if she declares bankruptcy and it was cashed during the lookback period.  But also be aware, the check could still bounce even with overdraft protection; she may have used it with other checks as well, and/or the bank could freeze the line of credit if they see her financial condition deteriorating.

Of course, once you have your money, you can always offer to assist with any cashflow issues she might have going forward.

Overdraft protection will pay a $2,000 check for someone teetering on the edge of bankruptcy?

OP - this really depends on your personal feelings towards her, your interaction with mutual friends, how amicable your split was, etc.  If you want a purely "finance" answer, of course cashing the check is the right thing to do.  Business has no emotion.

This is much more personal decision related than finance related. You'll get both sides of the coin here. Some are more "moral" than others here. Personally, I'd just write it off (as you should have done when you loaned the money, like most people say) if you truly don't want to kick her while she's down. If any part of you thinks you may regret that decision later, take the money and go about your life. Any written contract or promissory note?

She owes you money and wrote you a check. You no longer have access to her goods that you were renting. This is a question?

@dcwilbur - Just stopped by the bank that the check is drawn on and they verified my check would clear if I deposited it at my bank today, they needed to call her for verification if they were going to cash it (didn't feel like poking the bear today).

jaytader - No written contract, I covered some mutual expenses for a vacation we took in Europe and the deal was that I would cover everything and we'd split the balance 50/50. I made the mistake of not demanding immediate payment when she didn't have the ready cash when we returned.

I'd cash it. The money is yours, not hers. Otherwise you probably won't ever be able to recover it, which means you'll be giving your ex a $2,000 gift.

Cash it. You can give her $2000 later in the unlikely event you change your mind.

....I'm in good financial condition....


Whatever that means to you. If you'd never miss the 2k I'd consider a gift & never collect on it.

I was given advice long ago if I "lend" money to a loved one or a friend. Then it's a gift & never expect to get it back. So if I can't afford to lend the amount or I'll be resentful if I don't get repaid. Then I don't loan it out.
 

If your still attracted to her, you can have her work it off via other means... LOL.

pic?

Cash it and post pics of ex

Sounds like you wouldn't miss the money terribly and that she would. It is also apparent that you have some compassion for her still and would feel bad about putting this additional hardship on her, especially now at her busy season. My advice, follow your heart and don't cash the check. Either consider it a gift and let it go OR let her know that you would feel better about it if she paid you some smaller amount of xx per month until she is better able to pay off the remaining balance. If it were me, I would call it a gift and feel good about it. She will feel the pain of paying the money back to the bank but it's just a paycheck to you... You already know what to do though, don't you?

zapjb said:   
Whatever that means to you. If you'd never miss the 2k I'd consider a gift & never collect on it.

I was given advice long ago if I "lend" money to a loved one or a friend. Then it's a gift & never expect to get it back. So if I can't afford to lend the amount or I'll be resentful if I don't get repaid. Then I don't loan it out.
 

  That is good advice, but the question here isnt if he should pursue repayment of the money.  Its if he should refuse the repayment he has in his hands, whether he was expecting it or not.

I'd try to have her write you something like several checks amounting to $2000, with various dates. One for right now, and others for after her busiest business season of the year. If her business is not on healthier footing after its busiest season (I'm assuming it's also time for most revenue generation), then it'll probably go under and I'd rather the money be a write-off for some lender than for me. So make it so the last check coincides with shortly after the end of the busy season.

Overdraft protection isn't as great as a lot of people think. I wouldn't cash it since it will probably bounce anyway.

Glitch99 said:   
zapjb said:   
Whatever that means to you. If you'd never miss the 2k I'd consider a gift & never collect on it.

I was given advice long ago if I "lend" money to a loved one or a friend. Then it's a gift & never expect to get it back. So if I can't afford to lend the amount or I'll be resentful if I don't get repaid. Then I don't loan it out.

  That is good advice, but the question here isnt if he should pursue repayment of the money.  Its if he should refuse the repayment he has in his hands, whether he was expecting it or not.

  If he abides my suggestions then the answer is clear.

Shandril said:   I'd try to have her write you something like several checks amounting to $2000, with various dates. 
  They may have a cordial relationship, but this request would be a bit much for almost anyone.  A check is a legal promise to pay, and she could be on the hook for all of them if OP got vindictive and cashed the lot in one go.

/edit:  I misread your comment as suggesting that she write several checks for $2000, with the OP only cashing one of them.  I don't know why I thought that made sense.

I'll leave my original post intact so that the rest of you can laugh at my shame.

If her busiest season is sales for the holidays, can you agree to cash it Dec 31st?

Not sure if you cashed it already or not. But I'd suggest you cash it now, or write it off forever. The heat of the breakup is only going to cool off. If you don't cash it now and try some of these other ideas; like having her write you multiple smaller checks, wait until she's through the busy season, etc. you'll just be dredging up the breakup again. She could be upset at you at that point for even bringing it back up. She's given you a chance to get paid, if you pass on it, pass on it for good.

The more I think about this, the more I see her actions as a bit of a dick move. She's the one in a tight spot, so maybe that's the best she can manage. But given what OP knows, I think her options in descending order of The Right Thing would have been:

1. Give OP the check and don't bother him with the costs & complications that are likely
2. Tell OP that she still really can't pay it all. Pay what she can now and give honest expectations about when the rest can come
3. This is the one she picked. Make a gesture to pay it all as agreed, but make sure OP knows about her troubles, hope he takes pity and gives her a break without actually asking for one
4. Tell OP to pound sand, see advice above about loans vs gifts

I'm all for helping out someone who needs it when you can, so I'm not suggesting OP should justify handling this harshly. But if in the full picture of their relationship, his financial situation, impact his handling will have on relationships with others, etc he decides to cash the check now, I don't think it would be fair for him to be the bad guy.

SlimTim said:   The more I think about this, the more I see her actions as a bit of a dick move. She's the one in a tight spot, so maybe that's the best she can manage. But given what OP knows, I think her options in descending order of The Right Thing would have been:

1. Give OP the check and don't bother him with the costs & complications that are likely
2. Tell OP that she still really can't pay it all. Pay what she can now and give honest expectations about when the rest can come
3. This is the one she picked. Make a gesture to pay it all as agreed, but make sure OP knows about her troubles, hope he takes pity and gives her a break without actually asking for one
4. Tell OP to pound sand, see advice above about loans vs gifts

I'm all for helping out someone who needs it when you can, so I'm not suggesting OP should justify handling this harshly. But if in the full picture of their relationship, his financial situation, impact his handling will have on relationships with others, etc he decides to cash the check now, I don't think it would be fair for him to be the bad guy.
 

  Op just broke up with her, I'd assume he already had a good sense of her financial situation and she didnt "make sure he knows about her troubles" before giving him the check.  And he simply asked if the check will clear, and she simply responded that it will because she has overdraft protection.

Update: talked to some friends and some of my family, thought about it a bit more and realized the question doesn't boil down to "am I screwing her", it boils down to "am I screwing myself"?

I fronted money for a couple weeks in good faith to make things easier and cheaper for both of us during vacation. When she didn't have the cash when the loan was due (at the end of the vacation), I was generous enough to float it at 0% for half a year. The note comes due and I'm getting guilt tripped on how she's having money problems. As I think about it, I was a pretty darn nice guy to hold off collecting this long. Today she complained that she only has $2,500 in cash total and her and the business have $6,000 in bills due. That's extremely unfortunate, but she's around $500k-$600k in debt all together; me writing off $2,000 doesn't fix the problem, it just delays the inevitable by a month max.

Overall, if I can't sleep tonight and am racked with guilt, I can get an envelope full of hundreds and drop it off at her home or office tomorrow. I was already out with a much hotter girl last night, so I have new financial priorities. She has some very wealthy family (including the family she bought the business from) and if they want to take responsibility and help her out, that's a great thing for them to do. It's not my job anymore.


EDIT: Stopped by a branch of the bank the check was written on and tried to cash it yesterday, I was told they would have to call to verify the check was legitimate.  Not ideal, but they couldn't reach the ex and told me to come back. They verified funds so I just deposited it at my bank.  We'll see if it bounces....

OP, thanks for the update and your explanation of your reasoning.

-----
The additional details that you were still going out for 6 months after the vacation BUT she didn't try to pay anything back to you during that time, that she is a substantial $500,000 in debt with her business, and that she comes from a very wealthy family from whom she bought the business, do give a different spin on things than I imagined from reading the first part of the thread.
I had imagined that you had broken up with her right after the vacation during which you had floated her the $2000, that she wasn't in so much business debt as she is, and that she was from a non-wealthy family who didn't have business dealings with her and who couldn't help her financially.

Even if someone has very little, if they agree to go on such an expensive vacation that they agree to pay their fair share of, and then ask for a substantial loan from the travelling companion during the vacation, and afterwards they do not quickly try to start paying it back (not even offering a small recurring amount, such as "Can I pay you $50 or $100 per month, starting with my first payment today, and do that until I can get my business turned around, when I'll give the rest to you in a lump sum?"), then that isn't very honorable in my opinion -- it sounds like she assumed that you'd just cover that part of the vacation for her without bringing it up again or expecting repayment.

(Though she might be quite used to boyfriends/family treating her like that, and we strangers here don't know how your relationship worked in general with who paid for what and when; maybe given the overall dynamics, she wasn't being as grasping or 'entitled' as it might sound, though maybe she was.)

-----
Let the thread know if the check goes through okay and if there's any fallout that you know of.

BigManonCampus said:   ... she's around $500k-$600k in debt all together; me writing off $2,000 doesn't fix the problem, it just delays the inevitable by a month max.
 

  That says it all. Cash the check (hope it clears) and call it a day.



BigManonCampus;19645691 said:Update: ..I was already out with a much hotter girl last night, so I have new financial problems

Corrected for you

Update, check cleared. I was pretty surprised but also pleased. I can only assume she's knocking on bankruptcy's door and I'm quite hopeful that this check doesn't somehow drag me into it down the road. Overall, I'm sleeping great at night and it's nice to have the extra cash in the bank.

"but she's around $500k-$600k in debt all together" Wow, what kind of business is that? ya, I know it's not related to the OP.

BigManonCampus said:   Update, check cleared. I was pretty surprised but also pleased. I can only assume she's knocking on bankruptcy's door and I'm quite hopeful that this check doesn't somehow drag me into it down the road. Overall, I'm sleeping great at night and it's nice to have the extra cash in the bank.
  Just because your bank has given you access to the funds does not mean the check has cleared.

@ZenNuts - It's a business she bought from a family member, she took out a $500k SBA loan to buy the business and has some credit cards and lines of credit on top of that.

@Glitch99 - I suppose that's true, they held the funds for 3 days and today the entire balance was available in my account.

I'm late to the party but since everybody is looking for me to respond in a thread about a relationship gone south, here's my two cents.  

You broke up, you no longer have a physical or financial interest in her.  Cash that check and move on with your life.  Besides, you donating $2000 to her isn't going to save her from going bankrupt if her business is failing.  

The only way I would forgive the debt is if you thought 2am booty calls were a probability.  You go on a date and strike out, you're kinda drunk, you text your ex 'Hey, whatcha doin?' and she's at your house 20 minutes later.  You can't buy that for any price muchless $2000.

Well having the new info of xgf being 500k in debt before my 1st reply. I am changing my answer. I now agree with OPs chosen path.

kriskos4 said:   I'm late to the party but since everybody is looking for me to respond in a thread about a relationship gone south, here's my two cents.  

You broke up, you no longer have a physical or financial interest in her.  Cash that check and move on with your life.  Besides, you donating $2000 to her isn't going to save her from going bankrupt if her business is failing.  

The only way I would forgive the debt is if you thought 2am booty calls were a probability.  You go on a date and strike out, you're kinda drunk, you text your ex 'Hey, whatcha doin?' and she's at your house 20 minutes later.  You can't buy that for any price muchless $2000.

Actually you can get the kind of service for 2k

scrouds said:   
kriskos4 said:   I'm late to the party but since everybody is looking for me to respond in a thread about a relationship gone south, here's my two cents.  

You broke up, you no longer have a physical or financial interest in her.  Cash that check and move on with your life.  Besides, you donating $2000 to her isn't going to save her from going bankrupt if her business is failing.  

The only way I would forgive the debt is if you thought 2am booty calls were a probability.  You go on a date and strike out, you're kinda drunk, you text your ex 'Hey, whatcha doin?' and she's at your house 20 minutes later.  You can't buy that for any price muchless $2000.

Actually you can get the kind of service for 2k

  
Yeah...maybe 4 times for 2 grand.  And you have no idea what you're gonna get....an ex-gf knows what you're into and is good at it.  And with an ex-gf, you can rinse and repeat for months or years.

IANYL

In California you can take another's funds to apply to a debt only if you have a judgment in your favor. Absent a judgment, it might get treated as a petty theft or an embezzlement (civil or criminal). Why take a chance?

Your cashing a check someone wrote you can be considered petty theft?! Really?

Skipping 2 Messages...
Crazytree said:   IANYL

In California you can take another's funds to apply to a debt only if you have a judgment in your favor. Absent a judgment, it might get treated as a petty theft or an embezzlement (civil or criminal). Why take a chance?

What? OP was given a check in good faith. He has no intention to defraud another creditor...



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