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Michelle Singletary
Washington Post Columnist
Thursday, January 31, 2008; 12:00 PM

Personal finance columnist Michelle Singletary hosted an online discussion with Jeanne Fleming and Leonard Schwarz, the authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press, $21), on Thursday, Jan. 31 at Noon ET.

This Story

In her column from Jan. 6, Michelle writes that the authors provide tips for diffusing the uncomfortable and potentially hostile situations that occur when you mix money and personal relationships.

The transcript follows.

Read Michelle's past Color of Money columns.

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Michelle Singletary: Welcome. This should be an interesting chat. So let's get started.

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New York, N.Y.: Hi! My ex-friend and I agreed to meet regularly for lunch and take turns picking up the check, but then she started bringing her mother along, so when it was my turn to pay, I had to pay for three people, not one. But when it was my friend's turn to pay, she paid for just two people, because her mother always paid for her own meal. It was never her mother's turn to pay. Don't say that I should have brought my mother along, too, because I couldn't, because she had died.

I tried unsuccessfully to get my friend to see that this wasn't fair to me, but she just couldn't see it. And she was a Phi Beta Kappa and Dean's List and had a Ph.D.. But she wouldn't agree that I wound up paying more than she did. That's why she's my ex-friend. How would you have convinced a friend that this situation wasn't equitable?

Leonard Schwarz: Where did she get all those honors and degrees, the Univeristy of Self-Indulgence & Ethical Bankruptcy? You are never going to convince this woman that the arrangement is unfair, because she doesn't want to be convinced. We suggest you make her not only an ex-girl friend but an ex-lunch date.

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LaPlata, Md.: Michelle,

I have a quick question. I just bought a second house and now I am thinking about moving in with my boyfriend who I have dated for the past 8 years. I have no immediate plans of marriage and neither does he although we are planning to get married at some point in our lives. He wants me to add his name to my mortgage and I insisted that this is not a good idea. He feels uncomfortable paying rent/mortgage for a place that is not legally in his name. Is this really a good idea? I know what the implications could possibly be if I add his name to my mortgage but how do I protect my assets and my relationship at the same time?

Leonard Schwarz: Does he want his name to go on the mortgage (which would make most of his payments tax deductable) or does he want his name to go on the title (which would make the property half his)? ... We suggest you see a lawyer about this. Sounds to us as if he wants half of what's your -- half of what you paid for. How can that be fair?

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Rockville, Md.: My boyfriend and I have been together for 2 years and we've gone on several vactions together. I always take care of the travel arrangements because he moves slow and things would be sky high when he got around to doing it. I generally also take care of the financial aspect whether I pay or use my frequent flier miles. Our last vacation was supposed to be "his" vacation that he planned by himself and paid for but of course he moved slow so I did it. The trip cost about $3,000.00. Right after the trip, we both started new jobs and he is now making considerably more than I am with less expenses. When I've asked him for the money back he started arguments and said it was all about the money with me. I hinted to the fact that I was broke but that started another argument. I took a second job but I still haven't been paid back despite telling him about it. He's taken trips of his own and done other things but I still don't have my money. How can I prevent this from occuring again in the future? What do you suggest?

Leonard Schwarz: There's an old saying, you can't get blood from a stone. Hate to say it, but your boyfriend sounds like both a cheapskate and a deadbeat. So to answer your first question, the best way to prevent this from happening again in the future is to NEVER advance him any money. And to answer your second question: perhaps you need to find a more honorable boy friend.

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Maryland: Hi Michelle,

My brother has a live-in girlfriend, and he pays all the bills - living expenses, groceries, ultilities, activities, etc.. She pays for nothing, and then routinely gets upset when he refuses to buy six $90 tickets to a show she wants to see. Her parents also seem to be very interested in the amount of money he makes, and go so far as to suggest he pay for bills for which he is not responsible for.

To his girlfriend's credit, she does make about a sixth of what he earns, but I find it astounding that she will buy $4 cups of coffee from Starbucks, gym memberships and clothing, but then turn around and insist she has no money for bills. I don't understand how she (and, really, her family) can expect him to constantly pick up their tabs, while she spends money as she pleases!! Furthermore, I don't understand why he lets her get away with it!

Leonard Schwarz: Love and economic illiteracy are the answer. Love seems to have blinnded your brother to the fact that his girl friend is exploiting him. And economic illiteracy has led everyone but you not to notice that the money she should be spending on necessities are going to self-indulgences. ... It's not wrong for your brother to treat his girl friend to some nice things since he makes much more than she does, but it's very wrong for her to look to him for her general support.

Michelle Singletary: Ok, I know I'm going to get in trouble but here goes.

First, I understand your concern about your brother being taken advantage of BUT:

-- He's a grown man.

-- He's shacking up. No concern about that?

-- He's acting like a husband without all the commitment of a husband so if the little gold digger is taking advantage of him he should take it like a man (not a husband)

-- Is he complaining?

-- Grown people in their right mind will only let something like this happen to them because they want it to happen. If he were upset enough that it really bothered him he would kick her to the curb.

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Washington, D.C.: I'm a senior level staffer on the Hill. I recently started seeing someone who I really believe is just the type of person I want to be in my life long term, we both seem to agree. Because of a divorce and coming from a non-wealthy family, I don't have an abundance of money to throw around. She on the other hand, comes from a great background and has inherited a great deal of wealth. She never makes a big deal of it, and has not in any way said or did anything to make me feel inadequate, but I do personally. I feel like she deserves the best, I just don't always have the resources to give it to her. How do I work through this with her without drawing even more attention to what I don't have? How do I beat the personal feeling of inadequacy associated with it?

Jeanne Fleming: The first thing to remember is that the situation you're in is really common. The second is that she's already figured out that you don't have as much money as she does she, and she is interested in you ... so stop feeling inadequate. When you've known each other for a while -- say, close to a year -- start talking directly about what your financial resources are. When you're an established couple, you do need to figure out who's going to pay for what.

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General money question...: First of all, I love your amazing advice!

I have a question for you that I've been rolling around in my head for a while, wondering if I can get your opinion 1. I am 23, earning $47K a year. 2. I have $13K in a MMSA (currently earning 3.5%), and am contributing (after the company match) 12% in my 403(b). 3. My only debt is $13K in student loans, and 13 years left to pay them. $10K of this is at 2.6% and the other $3K is at 4.5%. I have been paying just the minimum on the student loans, but am considering taking $3K to pay off the higher-interest one in one lump sum

Aside from $5K as my emergency fund, all of my savings is there for a "someday" house and/or a "someday" wedding. The soonest either of these would happen is in 2 years, but I am aiming for that ideal 20% down payment, which in my area, takes a LONG time to save for. What do you think? Pay off the smaller loan, or keep the cash in savings? Either way, I will continue to save about 35% of my take-home pay in the MMSA.Thanks!

Michelle Singletary: If it were me and I had $13,000 in savings of which $5,000 is earmarked for emergency I would take the remaining $8,000 and get rid of as much of that student loan debt as possible. Then finish up the $5,000.

Then you are debt free and FREE to start your home, married life off in much better shape then many others in this country.

As I've said before don't hang onto student loan debt like it's a pet. The difference in what you are earning on the savings vs. the interest rate doesn't impress me enough to keep that debt. And even if it did I would still get rid of the debt.

Then take the payments you were paying on the debt and add it to your saving for a home or wedding fund.

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Eating Out: The worst is eating out with people that have different values than you. We enjoy spending time with another couple but they always want to order many drinks and appetizers when we go out to eat. It drives us nuts. Then they want to split the check and that should not even happen since there should be separate checks. I don't want to pay for someone's fried spinach!!

Michelle Singletary: Just take control of the outtings. Be the adult that you are.

At the beginning of the meal without any discussion let the wait staff person know there will be two checks. Don't argue. Don't discuss. Don't judge. Don't say anything more.

Just, "Would you please run two tabs. Thanks very much." Then say to the couple, "So what looks good to you."

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Anonymous: Thank you so much for your commonsense guidance. My husband is a professional athlete with a much higher income than we ever envisioned. We come from upper middle class backgrounds, but still make substantially more than our families and friends. We still live fairly frugally (4 BR house in the 'burbs), and we tithe and then contribute some to charities and intend to help with college for our nieces and nephews. However, we have been so overrun with dubious requests ("if your kids have a grand piano, ours should have one, too") we have now hired a financial adviser solely to determine how the money we have earmarked for family and friends can be used. Of course, we still have the final say, and there's no question we would help out with medical expenses for our parents and the like. The questions you've listed have already made an impact on some of our financial decisions. Thank you so much for your help.

Michelle Singletary: You are so welcome. And I LOVE your idea of a family fund.

When I was doing financial workshops for rookies for the NFL Players assocication I created just such a fund. I called it the Family/Friend Fund Account"

The idea was the NFL rookies would set aside a set amount of money to help family and friends. Then they decide what type of requests would be funded given how much money was in the fund. So for example, I suggested they help out with college, perhaps a downpayment of someone to buy a home they could "afford," medical expenses, etc.

And ALWAYS the check or cash would be given to the vendor.

If requests came in outside what thy wanted to fund they could or should say without guilt I don't pay for that. I do believe that to whom much is given much is required. But you don't have to be a sucker for triflin relatives who want you to buy their kid a grand piano.

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Learning Lunch Lessons Early: In my early twenties, I initially went out to lunch at work with large groups for special occasions. There were two ladies who always took the check with their calculator and told everyone what they owed by what they ordered. No problem. One lunch I attended NEITHER one of these ladies attended. This lunch was running late so I gave a co-worker my fair share & tip for the bill and left. Later on she caught up with me and told me that the bill was split with equally non-beer drinkers (she and I) and the big beer drinkers. This poor women was stuck with paying a much higher bill. I mentioned this to another coworker and she said "I only go to luncheons when I know that Alice or Betty will be there to split the bill!!"

From that moment I only went to luncheons that Alice or Betty attended.

Leonard Schwarz: In situations like yours, many people -- when Alice & Betty aren't around -- ask for a bar tab separate from the food tab. Then the drinkers split that, while the eaters split the food check.

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Charlottesville, Va.: For my aunt's birthday my uncle offered to pay for me and my parents to fly down from D.C. to Florida. My mother feels awkward about accepting the invitation since it is her brother in law who offered to pay. I say he would not have offered if he could not afford it. My aunt and uncle, I should add, make significantly more money than my parents so I feel it really is no problem financially for them.

Round trip airfare for the three of us is about $2,000. Again, we know they can afford it without any problems.

Should we accept or kindly pass up the offer? We cannot afford to go otherwise.

Jeanne Fleming: Your uncle is treating you and your family to something nice, and it sounds like there's no reason why you shouldn't accept (he can afford to treat you). Two things, though: Be sure to reciprocate (say, with a particularly thoughtful gift for your aunt and a festive meal out for the family) and think twice about accepting the next very expensive treat from him (unless you want him to become your family's patron, that is).

Have a great time!

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Houston, Tex.: Dear Michelle,

Thanks for the great chats! I love your advice. I had a question regarding high interest checking accounts at online banks like ING direct or HSBC. How safe are these? Are they like any other checking account?

Michelle Singletary: You are so sweet. As for the online banks if they are FDIC insured they are safe. ING is.

Not sure of their fee structure but of course you want to make sure what you get in a great interest rate for your checking and savings isn't eaten up in monthly fees. But the online banks because they don't have the cost of running a brick establishment can offer better rates. But also check your bank, credit union, etc. Go to www.bankrate.com to check on rates.

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Seperate tabs at dinner: After going out with a a couple of friends and spouses for dinner to a prix fixe @ $30 each, that wounded up costing my husband and me $160 after tax and tip, we started asking for separate checks at the beginning of meals too.

The first time you're nervous, you don't want to offend anyone, but after that it's easy. It's also hilarious to watch their faces when they get their specific bill and they realize that yes, the were drinking $20 glasses of wine, and no, we were not going to pay for it anymore.

Michelle Singletary: LOVE IT.

People be bold. Stand up for yourself.

Just love ths story.

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Just wanted to say to wife of pro athlete...:...that was a refreshing post. Nice that you are living fairly modestly, tithing and helping family and friends. What a nice post to read.

Michelle Singletary: Amen!

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Alexandria, Va.: The crux of your book is that parents and others can pretty much spend and leave money as they desire. But can't you at least agree that fair is, or should be, fair? Sis went to UVA undergrad nd law school, and had a $30,000 wedding, all paid for by my parents; she has no student debt and is a 3rd year associate on Wall Street making something like $200,000 a year, and her husband is in-house counsel for a large corporation. I am not academically inclined, married out of high school at the county courthouse, and my husband and I are struggling to raise 2 children on around $50,000/year. I know things could be worse but hate it when parents say this is my own fault for wasting my life and not living up to my potential. Sister and husband take my parents on Mediterranean cruises and give us generous checks ($1,000+) at Christmas and birthdays, which makes me feel alternately deprived and beholden. Can you give me some perspective on this? Thank you very much.

Leonard Schwarz: Your parents are wrong -- very wrong -- to denegrate the choices you've made. Your life is yours to live as you choose, assuming you are not imposing on others or expecting them to help support you. However, you too must recognize that the wealth gap that exists between you and your sister is a result of choices each of you made. But there is no need to feel beholden to her. Presumably her generosity toward your family comes from her love for you.

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Santa Fe, N.M.: Michelle--

I did my taxes! YAY! I was spot on with my state withholding, which has never happened before, and the feds are giving me something like $300. I just wanted to give credit where credit is due -- I adjusted my withholdings last year around this time as a result of what I read in one of your chats. Not having to stress about paying is really nice.

Thanks.

Michelle Singletary: Oh how nice. Thanks for letting me know.

But really the credit goes to you. You it's easy for me to give the advice, much harder for people to take it.

So good for you.

Now what are you going to do with that $300 (smile).

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Washington, D.C.: I never have the check splitting problem when I go out with my friends. The biggest problem is usually ending up with too much money after the check has gone around and we've put our portion in. We always split according to our order.

It is crazy to me that anyone would do otherwise!

Michelle Singletary: So funny.

Good friends you have.

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Maryland: I was reading through the transcript of the last chat, and I wanted to say something to the person who was recovering from depression.I was in their shoes 6 years ago. I nearly got evicted from my apartment, had over $15,000 in credit card debt, and was behind on all of it.

Your advice was spot on. I got treatment, went to credit counseling and paid off all of my credit cards. (And refuse to ever use one again!) I went back to school and got a degree and got a better job. And last year I was able to buy my first house. So yes, it's possible to come back from it! Just keep paying payments for everything on time, and things will naturally improve.

Michelle Singletary: Thank you so much for sharing your story and hope.

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Caldwell, TX : I am widowed, on a fixed income, and have 2 daughers, 33 and 28. The older is a lawyer who married well. They live in a mansion in a gated community. Their house has a swimming pool and a 3 car garage. They drive a Jaguar and a Range Rover. The younger is a single mother of 3 small children who has never caught a break. Of course I give all I can to her, and will leave her whatever I can. My older daughter disapproves, and says I am enabling her dependent lifestyle. But with 3 small children and no skills or training, what else is possible? She's a talented artist but can't afford training. My older daughter takes me on trips but won't give me money because she doesn't want it to go to her sister. She somewhat grudgingly assures me she will see that her sister "doesn't starve" after I'm gone, but I find that small consolation. Is there some way I can turn her into a more loving sister? What did I do wrong? Sad Mom in Texas

Jeanne Fleming: Your older daughter has a point. Think about what you can do to encourage your younger daughter to become financially independent, because in the long run that's the only real solution.

Michelle Singletary: I couldn't agree more with Jeanne. In many ways you may just ben enabling her to play the "I'm single with kids, you should help me."

Or maybe she isn't singing that song but since it's in your head you go ahead and give money when you shouldn't.

Stoping giving and you may be surprise what your daughter may do on her own to improve her situation.

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Fairfax, Va.: Hi, All. Friends and I have the little things down pat. We split the check only if amounts spent were fairly equal, and if someone with a lot of money wants to treat me to a meal or evening out (no one has yet offered to take me to Europe), I smile and say, Thanks!

Potential problem is, I am seeing a very nice man who is the only member of his family to go not only to college but to law school. We are both lawyers in our 40's, make pretty good money, have never been married, though I've had a couple long-term relationships. His family is not the "trailer trash" example used in your book, in fact, they seem like nice, hardworking people, but with little education, skills or training they are facing some tough times. Because he "had it better," even though mostly through his own doing, he feels responsible for their lives. He bought his parents a house, now paid off, some years ago and regularly helps out with medical and other expenses. I know Michelle is strongly opposed to a married couple having separate accounts, but I'm tempted to stash some money away in case his generosity increases to the point I find uncomfortable. I realize he is unlikely to change, and actually think this is a pretty nice trait, though contributing to the support of 12-13 people is pretty overwhelming. He has resisted my suggestions that he set limits on his giving, says he considers all requests on a case-by-case basis, but it's awfully hard for him to say "No" and I'm afraid the more he gives, the more they are going to request.

Leonard Schwarz: You're right about two things. Your man sounds like a prince -- a generous responsibility-taker, to be more precise. And, second, if he can't say No, you have good reason for concern. If you're considering marriage, you need a household cookie jar that is off limits for his family and another cookie jar that is his to do with as he likes -- buy skis or fix a relative's car. You can't have all your joint funds at risk to his family's emergencies.

Michelle Singletary: I actually agree with Leonard and this can be done with joint accounts. But as he said if this is the "man" you should have this conversation often and negoitate to have certain family funds off limits as Leonard said.

If he can't agree to that, then your prince hasn't come yet.

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Washington, D.C.: Hi Michelle,

Thanks for the advice, and sorry in advance for the long question.

I over-withheld my taxes by accident this year (oops! Fixed it for next year already) and am getting a large refund. The amount of my refund is equivalent to about 6 months of minimum payments on my school loans (I have no other debt.) Ordinarily I would just overpay, but I'm competing for a prestigious 6-month fellowship that would reduce my salary. I have enough to pay the minimums while I'm gone in my emergency fund, but not much left in that after. Should I save the refund (and pay the extra interest) in case I get the fellowship? Or should I pay now deplete my emergency fund if I get it?

Thanks!

Michelle Singletary: In this case I would put aside the money for a time when you might have reduced income.

BUT as soon as that fellowhip is up get rid of that debt. If you do it won't limit you in the future -- like now.

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Washington, D.C.: My sister is getting married this summer and asked me to be the matron of honor. I couldn't say no (it would have devastated my mother), so I recently shelled out about $300 for the dress. Between the dress and alterations, travel expenses to the shower and to the wedding itself, and other things, I'm estimating that the wedding is going to cost us at least $1,000. I'm trying to say "no" where I can (I'm trying to gracefully bow out of the pedicures and fancy hair appointments), but where I'm stuck is on gifts. What are appropriate bridal shower and wedding gift amounts when you're already being asked to spend such a large amount of money on everything else?

Jeanne Fleming: The right amount to spend on any gift is an amount you can afford. Even if most people are giving your sister gifts that cost, say, $100, if what you can afford to spend is $25, that's fine. This is a joyous event, not a one-way ticket to bankruptcy.

Michelle Singletary: That's right. Give what you want, can afford.

Be true to yourself financially.

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Chantilly, Va.: Thank you so much for your common sense guidance. Now my husband and I just have to implement it!

You could almost use us as a "final exam" question if you taught a course based on the book. We have 5 grown children, one with chronic fatigue syndrome and one with chronic disabling depression. The other 3 are professionals, 2 doing very well but the 3rd does not handle money well, and despite a good income is frequently asking us and his better-off siblings for help, which he does not repay. Fortunately, we are pretty well off and have established trusts to help the 2 with problems receive the care they need, most likely for the rest of their lives. The question is, how to treat the other 3? We're tending towards equal treatment even though one has received much more than the others. We know there is no "right" answer for this, but we are still torn.

Leonard Schwarz: You're right, there is no perfect solution here. First off, before you decide to divide things evenly, ask yourself why that is fair. Specifically, shouldn't the love, attention and support you've received from each of your children influence your decision, just as the disabilities of two of them did? Secondly, if you divide the remainder of your estate between the three professionals and take no account of the fact that you've been helping to support one of them, you are, in effect, punishing the other two for their prudence. All of which is not to say that you shouldn't divide things three ways. But do consider these other factors ... and good luck.

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Washington, D.C.: Here's a good one for you -- my sister and I had inherited our parent's house (and my sister continued living there). She felt it was my duty to subsidize her and pay half of all repairs even though I had my own mortgage/family to take care of. She eventaully bought my share but we don't speak much now.

Jeanne Fleming: There are three areas where money-and-relationships trouble is most likely to emerge, and inheritances in one of them. Your sister, of course, was being completely unreasonable. I hope the two of you can one day return to having a closer relationship, but in the meantime don't forget that you weren't the bad guy here.

Michelle Singletary: I agree with Jeanne. So going forward why don't you send a card here and there, call her on her birthday, holidays. Reach out --even if she hangs up the telephone.

Do what you can to keep the lines of communication open. After that it's on her. One day she will (hopefully, prayfully) realize how wrong she was.

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Bethesda, Md.: What advice would you give if you are in business and a personal friend runs for office and asks for a campaign contribution? You know it is not going directly to your friend and you may be concerned that too large a contribution might even hurt, as people may claim your friend is too close to the interests of your business. Yet you may not want to give too little and insult your friend. Do you have any ground rules for this situation?

Jeanne Fleming: You're right to be concerned. Why not start by discussing these issues with your friend and seeing what he or she has to say? And don't worry about giving too little: There's nothing wrong with saying "I'd love to help, and I think I can contribute about $x. Wish I could do more!"

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New York City: Michelle,

I was interested in what you said about strings being attached to gifts or loans. Can you elaborate on your thinking? My family has always felt a gift is a gift. Of course, we never had much so a monetary gift was never more than $100. My husband's family (but not my husband), on the other hand, are very wealthy and all gifts of money came with strings attached. His family offered to pay medical bills that wouldn't be covered by insurance only if the payor was given full access to the doctors to monitor progress (and all checks were made to the vendors). Some gifts to some members of the family are free of strings, other gifts to others are not. Once a gift is accepted, you are basically held accountable for some unspecified length of time - based soley on the capricious nature of the giver. I'm to the point where I don't want to accept ANYTHING from his family. He's getting to that point, too, but isn't quite there yet.

So, when are strings appropriate?

Thanks!!!

Leonard Schwarz: In general, there is nothing wrong with attaching a string to a gift. After all, the recipient doesn't have to accept the gift if they don't like the string. The main exception would be gifts with strings that exploit the desperation of the recipient (e.g., telling a daughter in desperate economic straights that you'll give you money if she agrees to put a child up for adoption) -- that's dishonorable. You're father-in-law appears to be approaching another dishonorable arena -- using the gift to invade the privacy of the recipient (i.e., access to doctors) And, more generally, it sounds like he is very interested in control. Shame on him for being so manipulative. But the bottom line remains, if you don't like the string, say no to the gift.

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Virginia: I've been married for 5 years. At the beginning of the marriage, I was making good money, but spending way too much on personal luxuries - which I was hiding from him. I have since realized my errors, and now live according to a budget. About a year ago, my husband paid (out of his personal savings) about $30K in my high-interest student loan debt and $10K in my credit card debt, to wipe my/our slate clean. Our debt now is confined to a small, reasonable car loan (almost done) and my 2% interest rate student loan debt (there is a lot - more than $50K). Due to a valid health issue, I can no longer work. I feel terrible about the debt I caused him, and put him behind on his/our financial goals. Given my inability to work now, I feel my hands are tied to make this up to him - his financial security is much less due to me. I do what I can to make his and our life nice and happy, but the reality is that the money I wasted is never coming back. He is frustrated by it, too - he was living frugally, and I was wasting money, behind his back. He says he'd have no problem giving his life savings for me if I had an accident or tragedy, but it's continually frustrating for us both that I've put us behind on our financial goals in a significant way due to my frivolity and indiscretion. How can we move past this hump in our relationship? He doesn't hold it over my head, but we're both frustrated every time we look at our financial picture, and I feel just awful.

Leonard Schwarz: You can't beat yourself up forever over the mistakes of the past. All you can do is learn from them and be certain never to repeat them. You are fortunate to have a husband to be so accepting. Count your blessings.

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RE: Maid of Honor Gifts: In response to the maid of honor and gifts, I was in a similar situation. In lieu of a wedding gift purchased from the registry, I instead made the bride an "emergency kit" for the day of the wedding including asprin, tissues, nylons, mouth wash, mints, sewing kit, bottles of water, energy bars etc. Everything I could think of that would be great to have on hand. It cost about $25 for everything - and the bride loved it - and we used nearly everything on the day of!

Michelle Singletary: Good idea.

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Washington, D.C.: My boyfriend of 7 years recently proposed to me. As he was planning the proposal, he also planned a surprise engagement party at the house of some of our closest friends, for the evening after he proposed. He invited his sisters, who each live about 4 hours away, several of our local friends, and even some of his childhood friends, who live several states away. They all came on less than 3 days notice.

I am currently in a sticky situation as my (now) fiance also invited my best friend and college roommate to the party. She was very excited to come, but on 3 days notice, the train fare or airfare was out of her price range (she's a graduate student), and she told him so. He replied with, "well, of course I would pay for your travel." To him, it was important that she come for the party for my sake. She was terribly offended that he offered to pay, she felt like it was charity. He's offended that she turned him down, and seems to think she doesn't value our friendship enough to make the trip. And I'm stuck in the middle. Thoughts?

Jeanne Fleming: Well, this is a sticky situation.

Your boyfriend's heart was certainly in the right place when he offered to pay your friend's travel expenses. But there was nothing wrong with your friend declining his offer, either.

These two nice, honorable people should like each other. How about planning a reconciliation dinner -- and telling them each in advance that you love them both, and it's very important to you that they get over this. (And if dinner's in your town, give your friend plenty of notice and don't offer to pay her way.)

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Washington, D.C.: Hi Michelle,

I follow your articles religiously. I make $100K a year and my boyfriend makes $70K. We've been dating for 3.5 years. Previously, when we did stuff together we paid 50-50. That was when we were making roughly the same. Now I tend to pay roughly 70%. I do this voluntarily. Now, I don't want to make him feel bad, but I feel that that's fair since I make more. Does that make sense? He does treat sometimes and is not the kind of person who would take advantage of me.

Leonard Schwarz: Sounds like you have a nice boy friend. But the problem with you paying less than your full share is that this makes you, in a way, his dependant. Maybe your relationship is so well established that this is irrelevant, but be careful.

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Danville, Ca.: I have a relative who has a boyfriend who is very nice and very wealthy. Sometimes we are invited out with them--on yacht trips and dinner events. Frist question: how do you repay someone who pays for a week long paid trip on a yacht in the Carribean when they also paid for our children's air fare (we paid for our own).

Also when they want to go to dinner or when they visit us I feel like we have to pay but definitely cannot afford it.

What is the best way to handle this?

MRS. A

Leonard Schwarz: You repay him by doing something special for him. It doesn't have to be particularly expensive, just particularly thoughtful (a bottle of his favorite wine, a pair of tickets to a sporting event that interests him). If you can't afford to take to dinner someone who takes you to the Carribean for a week, perhaps you should say no to the next trip he offers. You of course don't need to reciprocate his generosith and graciousness dollar for dollar, but you do have to hit a minimum level, and we'd say dinner is definitely in order for a trip like that.

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Dallas, Tex.: You are a well-paid reporter at a respected newspaper involved in other media ventures and the crowd you run with deals with this kinds of issues?

I'm referring to the lady ordering the entire menu (basically) then you saying, no, I am only paying my share. That's kind of distasteful, on both of your ends.

But, thank you for this insight. As a recent college grad I thought only my broke circle was pinching pennies to pay our meals.

Now, I know even REAL grown folks who make a lot of money still fight over the bill.

Michelle Singletary: I see an insult in here. Of course I may be wrong but if I'm not poot you.

I run with all crowds -- well off, living paycheck to paycheck, low income, high income, etc.

It doesn't matter how much money you make you have a right to spend it how you want. I am not subsidizing other people's liquor at a meal. I typically order frugally. If you want to splurge then fine. But pay for it yourself.

Me, I choose to use those dollars for other things such as helping others go to college (Just sent $400 to a niece to buy books at Spelman. You give anything to anybody?)

Is that real enough for you?

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RE: Wedding Gift: When I got married, two of my friends had tight finances. Both actually told me that after paying for dresses (and one had to travel) that they were strapped. I appreciated them thinking enough ahead to tell me that and told them that their participation in my wedding was the best gift they could have gotten me.

Michelle Singletary: Good for you. Wish more brides/grooms were like you.

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I don't understand the problem: I don't mean to sound rude or harsh, but I don't understand paying for food you didn't order/didn't eat. My friends and I have been splitting the check SINCE HIGH SCHOOL. It's never been an issue or a problem. No one's grumbled or complained or said "it'll be easier this way". Why do people have such a hard time standing up for themselves and their finances?

Michelle Singletary: Because of people like the person who sent in the last question.

Somehow when you make money people think you shouldn't worry about money.

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Washington, D.C.: Hi Michelle,

Can you offer any advice on this matter? About three years ago I took a trip with my best friend. I took charge with the travel arrangements because she is a procrastinator. As a result, I used my credit card to pay for the airfare, hotel, etc. As of today she still hasn't paid me back for most of her expenses. Over the course of the last three years she has taken numerous trips throughout the world some of which she has paid and others where friends paid. I am resigned now to never receive my money back. It's actually not the amount that matters to me, but more the principle behind it. She's not the best with money and her income is iffy as she relies on singing/acting gigs. Do I just let this go or actually say something about it? Thanks.

Leonard Schwarz: You should have spoken up MUCH sooner -- nip it in the bud is the best approach when someone is slow to repay you. But certainly speak up now. She's the bad guy here; you have nothing to be embarrassed about.

Michelle Singletary: Totally agree. Why don't you make a copy of all the bills, credit card statements, etc. Send a nice note highlighing her charges. Ask for your money.

If she doesn't pay up after that you have two choices:

a.) consider the money a gift

b.) kick her to the curb

If you value the friendship and drop it if you can't collect. But NEVER ever pay for her again.

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New York: My parents are retired and don't have a lot to go to an "estate". However, they have felt it very important to treat my brother and I fairly. My brother is in his 40s and has been subsidized by my parents for most of his adult life. He is now self-supporting and we are all very VERY happy and proud. He's had a rough time but he's been working hard. My parents decided quite a while ago that they would keep a running account of the money that was going to my brother. They decided that he was getting his inheritence early. Ultimately, when they do pass on, the estate will be liquidated and an executor will subtract the amount given to my brother and give it to me. What is left, if anything, will be divided equally between the two of us. My parents thought this was the best they could do under the circumstances.

Jeanne Fleming: It's great that your parents are keeping that accounting. But do take a look at it and make sure that it's precise and includes dates, amounts, check numbers, etc. (Their executor should have an up-to-date copy of this document as well.) And do make sure that your parents' will/trust includes language that insures that the amount your brother owes will be subtracted from his share.

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Washington, D.C: I just don't understand all these stories about people who have family members who make a good salary but still ask for help from parents, siblings, friends. Out of pride alone, I would never ask a family member for help. I would have to be on the brink of eviction for that to happen. I would cut out or sell everything else I have before that would happen. It just doesn't make any sense to me.

And honestly, the people that lend the money are even worse. If they "need", ask them first if they've sold that car, and bought a used one. Or if they cancelled their cable, or their cellphones. If they haven't, DON'T LEND!

Leonard Schwarz: You got that right. One of the most important things to consider when someone asks yo borrow money from you is what are their other options for raising cash. And downscaling their lifestyle is definitely on the table (and so is going to a bank).

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Jeanne Fleming: We have three rules for handling money-and-relationships problems: Nip it in the bud. Learn to say no. And don't forget who the good guy is (you, not, say, the guy who isn't throwing in enough money to cover his three martinis and big steak).

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Baltimore, Md.: I need some help. I am a contractor and I did some work in early 2007 for a friend on a house that he purchased to "flip". I told him that since we were friends, he could hold off on paying me until he sold the house in Feb/March 2007. Well, the market softened and he decided to hold off on selling the house indefinitely- and decided to hold off on paying me indefinitely as well. Well, he owes me $5K and I have no idea how to go about collecting this money.

Jeanne Fleming: If you haven't already spoken very directly with your friend about this, you need to. Right away. He needs to understand that just because he decided not to sell doesn't mean that you decided not be repaid. I hope you got your deal with him in writing (in particular, that the due date for payment was Feb/March 2007).

The next step, if your friend refuses to pay you, is probably to talk to a lawyer about what your options are for collecting.

If you're worried about offending your friend, worry less. He's over a year behind in paying you a large sum of money.

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Washington, D.C.: This is a very basic question, and I admit I have not read your book, but how do you start the "let's talk about money" discussion with your significant other without sounding like a lout. I make substantially more money than my boyfriend of more than a year, who I love very much. He also has signficant debt from student loans and other past events. We have talked about marriage, but I have some serious questions about whether we are on the same page about how we see our future financially. How do I bring this up without sounding like all I care about is money?

Leonard Schwarz: What's wrong with caring about money? Don't be defensive. To have a successful relationship in the long run, couples have to be on the same page with respect to money. If he thinks money is all you care about, shame on him. He's known you for a year and knows better. Sounds like he just doesn't want to hear what you have to say.

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New England: My brother makes a lot more money than I do. I don't even know exactly how much. He & his wife have been very generous in paying for us to fly cross-country visit them at Christmas. They say it is fair because they want to see us and we are going through the hassle & discomfort of travel. We don't mind the travel and there is more to do in their hometown than ours. We take turns treating one another while we are together for meals out, tickets, etc.

Is there a point where we should stop accepting? The first time this happened we had been hit with an unexpected expense and their support really helped me relax & enjoy the time together rather than envisioning the $ flying out of my account. The second time, I was surprised but grateful. Now it almost seems to be taken for granted by them that they pay and we shouldn't worry about it. We're close and I know they're good with money and not going to do something they can't afford, but!!! I never expected to be in this position & I just wonder if there may be future problems or things to watch out for.

Jeanne Fleming: You are right to be concerned. You need to decide whether you want your brother and his wife to be your peers or your patrons ... and if you keep accepting this money systematically, they'll be your patrons.

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Michelle Singletary: Well this has been a great chat with lots of interesting questions, comments.

Thanks to you all you joined me today. As alway my guests have agreed to answer some of the questions they couldn't get to in the time allowed. Please look for them answers either in my print column on in my weekly eletter.

Thanks again. And be safe and save.

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Editor's Note: washingtonpost.com moderators retain editorial control over Discussions and choose the most relevant questions for guests and hosts; guests and hosts can decline to answer questions. washingtonpost.com is not responsible for any content posted by third parties.


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