“My Boyfriend Hasn’t Paid His Taxes in Ten Years. Can We Still Have a Future Together?”

First of all, let me address your initial assertion that the reason I’m receiving fewer letters now than I used to is because my advice is “rather harsh and almost attacks the writer.” You are certainly entitled to your opinion, and if you think my advice is harsh, then it *is* harsh for your taste and that’s ok. But the thing is, my tone – the tenor of my advice – hasn’t changed all that much in the 15 years I’ve been doing this. I’ve been accused of being “too harsh” since I started. I’ve also been credited for giving really compassionate and thoughtful advice, too. The truth is probably somewhere in between, or a little of all of it, and different people are going to react in different ways, and sometimes my tone is more harsh for some LWs and less harsh for others, depending on the circumstances.

I suspect the more likely reason letters have dropped off this year is related to the pandemic and the fact that my elementary-age kids were home from school for 543 days and I, like countless other parents (especially moms), had to de-prioritize my work to supervise their remote school and tend to their needs all day, every day. Because of that, I posted far fewer times a week and readers started looking elsewhere for their daily advice and entertainment. Also, many of them were/are spending less time online, too, because their work had become home-based and/or they, too, were spending much more time supervising their kids who were learning remotely. In addition, there were some big changes last year in Google’s algorithms, which greatly affected my search traffic (more than any previous update), decreasing – by a lot! – the number of new readers who find my site through Google searches. But, ok sure, if you want to believe it’s the same tone and delivery I’ve had for fifteen years that suddenly drove everyone away, that’s obviously fine and your right to believe.

What’s interesting is that despite your perception of me as someone who almost attacks the people who write in for advice, you still decided to write to me. There are lots of advice columnists you could have written to, and if it was the DW community you want to hear from, you probably know that there is an active forum where you could have bypassed me and gone straight to them for advice, but you chose to interact with me directly. There’s an idea that we seek out the advice and counseling we want to hear, or think we need to hear. It’s like how a kid goes to the parent who will say, “Sure, you can have ice cream for dessert” instead of asking the one who is more likely to say “no.” I suspect that you came to the person who you feel is most likely to tell it to you straight, even if the truth is harsh and unpleasant to hear, because you know it’s what you need, and I commend you for that.

It’s often easier to hear from someone else that we need to do something we don’t want to do rather than have only ourselves to “blame” when we feel the inevitable discomfort of doing the thing we didn’t want to do but know is best for us. So, let me give you someone to blame for the heartache you’ll feel if/when you end your relationship: There probably is not a happy future in a relationship between you and a guy whose values differ so greatly from yours. This is more than his being irresponsible with money, which is something a lot of couples face and work through; your boyfriend is a criminal, he’s selfish, and he evades contributing his share to the communal pot that allows our society to run smoothly. He’s immature and irresponsible, and he doesn’t seem to respect the boundaries you’ve set for yourself (making fun of you when you carefully consider spending money on something). Frankly, he sounds like a real loser, and if my saying so is what you mean when you call me harsh, so be it. You sought out my advice for a reason and here it is: You’re better than this.

You’re better than this – than the promise of your relationship and the way you’ve sold yourself short – not because you make more money than Karl. You’re better than this because you’ve traded your scruples for someone whose redeeming qualities – if there are any – didn’t even warrant a mention in a letter to an advice columnist you think is harsh and attacks people. Yes, you say your relationship is loving, but you give no examples of Karl actually acting lovingly and you give no details of any of his positive traits at all. You didn’t even try to defend him against my potential attacks – which you must have been expecting – beyond saying that he doesn’t blow his money on drinking or gambling and that when you go out, you take turns paying. Yay?

Look, I can appreciate that the dating pool of a well-educated, professional woman in her 50s is different from what mine was when I was single and dating. I understand that you have to make some compromises in exchange for companionship and affection. But I still think you’ve set the bar too low. What do you think? Maybe you disagree. Maybe the companionship and affection is worth whatever you give up in dating this guy. But don’t marry him! Don’t merge finances. Don’t move in with him. Don’t do anything that would complicate your ability to walk – run! – away from him as quickly as possible. Because I do think there will come a time when you’ll want to leave, even if you aren’t quite there yet. And you might need the voice of a harsh, critical bitch to blame for the potential heartache you might feel, so here I am. But I promise the heartache will pass quickly when you realize you’re better off without him. Because you are.

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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.