WWYD: Judging Friends for Being Broke and Wanting to Have a Baby

A friend and co-worker of mine is on a mission to have a baby. She's always wanted to be a mom and finally at 34, she's in a fantastic, stable relationship with another co-worker who equally wants to be a dad. They're going to make fantastic parents. The problem is, they're broke. The bigger problem is that it isn't a problem for THEM and that strangely feels like a problem for ME.

The One With the Big Tip

Why don't we start this morning with a WWYD, but have you readers help me this time?

Paying for Dinner

I recently stayed with two friends while visiting their city, and to thank them I told them that I wanted to take them out for dinner.

“No, no!” they said. “We’re just happy to host you while you’re visiting!”

I planned to pay for dinner anyway, and when we went out to dinner on our last night and the check arrived, I pulled out my card and insisted on paying—but my friends ended up handing their card to our waitress and told her to just split the bill.

This may seem like a silly question, but is there a nice way of insisting on picking up the check? — B.

Should I Take This Low-paying Job in This Tough-to-break-in Field?

It's a rare opportunity, but here's the thing: It pays very little, with no room for negotiation and little room for advancement in the company (it's a startup). I'm afraid that after months of applying, this is the best I can get and I shouldn't turn it down since jobs are so hard to come by, especially in New York media.

WWYD: Prudie & The Ethicist Edition

Wouldn’t Prudie and the Ethicist be a good name for a band? Anyway. Someone wrote a letter to Slate’s Dear Prudence with a question that they should have pointed our way:

My good friend has found her mate after several failed relationships and is desperate to be married and start her family (tick tock). I am thrilled that she is engaged, and she has asked me to be in the wedding. I would normally be pleased to do so, except for one issue. She has debt of approximately $250,000 in credit cards and student loans, and she has not told her fiancé about this. I feel strongly that she is morally and ethically required to tell him before they are married, but she refuses. I can’t help but feel like an accomplice to her dishonesty by standing up in the wedding. What is the right thing to do? —Silent Accomplice

Prudie tells SA that she’s right to be squicked out: her “good” friend is perpetrating a fraud.

debt like this is something that simply must be revealed before two people wed. Keeping from your intended painful news, like a diagnosis of major illness, a previous incarceration, or the fact that you are dead broke (and not Hillary Clinton dead broke), means starting a life together based on an implicit lie.

Startlingly, Prudie does not suggest that SA write the clueless fiance an anonymous letter suggesting he follow the money. I wish we knew whether the bride were hiding financial truths from the groom or straight out lying. Either way, marriages have been based on deceit since the beginning of time. Years shaved off of ages, ex-wives forgotten, goats gone unaccounted for, paternity fudged. This can be seen as just another strike against the Wedding Industrial Complex, the societal idiocy that drives us to get married at all costs, often literally. Audits and prenups for all! Or don’t get married. That’s cool too.

Meanwhile, at the Ethicist’s lair …

I Found Out My Male Colleague Made More Than Me

I've been temping at Company X, a large company in Chicago, since the beginning of last August. I started temping here because I'd heard it was a good way to get hired on full time, and I liked the company. While I was here, my boss fought to get me hired, but she was turned down. I decided to change careers and go back to grad school.

The Medical Billing Snafu

Medical billing gone wrong.

How Do You Split the Cost of a Group Trip?

How do you split the cost of group trips?

WWYD With a Five Figure Check?

So, let’s say an elderly relative gave you a check for five figures as part of her estate planning, essentially an advance on your inheritance. Not a hugely extravagant amount of money, but quite a goodly sum, enough for one whole month of full-time long-term care insurance.

SIDENOTE: long-term care insurance is so hilariously expensive it seems insane that it could save you money in the long term, and yet Roz Chast’s new graphic memoir about the decline and fall of both of her aged parents, culminating in having to put them in a home, would scare any reasonable person into scrambling desperately to secure some kind of safety net for themselves.

Five figures! It’s not a prize, like the Pulitzer. It’s not salary. It’s not fun money, because it’s given in the spirit of Thinking About the Future. Obviously it’s not Quit Your Job and Retire money but it’s not nothin’. What do you do with it? Buy real estate, or ice cream sandwiches, or both? Invest in something? What? Put it in your IRA, or is that too boring and conservative?

Don’t worry, my fella and I are seeing an actual Financial Planner on Friday and so will get expert advice then, but in the meantime I’m curious. WWYD?

Impatient for the Life Ahead of Us

My husband, our two kids and I need to buy a family home and in order to make that happen we are going to need more cash. Right now, it's about earning more money. I want to stay in my current job with its attendant flexibility, and ideally I want to be paid more. I just am really dreading talking to my boss about a raise.

How Much Should You Tip for Office Food Deliveries?

I know this has been covered to death, but I have a question about institutional tipping. I'm lucky enough to work for a company that sees fit to provide its employees with a variety of free food - lunches, breakfasts, snacks, etc.

Buying a Gift For Someone Who Did You a Financial Favor

Recently he suggested I take a 'rent holiday' for a few months because I've got some other big bills to pay, which is a relief! However, it's also his birthday in a month and I had been thinking about getting him a Kindle — which now won't be that difficult to afford given the 'no rent' thing. What is the etiquette on how much to spend on a present for someone when they've just done you a financial favor?