Dear John: Cheapskate Dates

Dear John advises on cheap dates, taped sex without consent, and a friend torn between religion and honesty.

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Dear John,

I have been going on a lot of first dates lately and for some reason, my dates often under-tip the server. Maybe I shouldn’t glance over and see the total on the check and what they leave, but I do. Then, I feel badly about the measly tip. Last night, my date left a $5 tip on a $40 check! I wanted to open my purse and leave another $5, but felt it would be rude. A similar situation happened last week. I live in a small town and don’t want to be a labeled as a bad customer. Any suggestions?

I’m NOT Cheap

Dear Not Cheap,

I agree that supplementing the tip would be a bit rude. Maybe these guys are cheap, or maybe they’re a little strapped for cash. Lots of people are these days, so let’s give them the benefit of the doubt. Next time you’re out to dinner, when the guy reaches for the check, thank him for being so generous and say you’ll get the tip. Your server will be happy, and all those small-town tongues will have to find something else to wag about.

Dear John,

I am writing to you about a situation that has left me badly shaken and very angry. My boyfriend of approximately one year revealed to me that he videotaped us having sex without my knowledge! He told me this as if he was letting me in on a harmless practical joke. When he saw how upset I was – which was more upset than he’s ever seen me about anything – he apologized profusely and said he thought it would be fun for us to watch together. He seems genuinely sorry and shocked at how angry and hurt I am, but I’m not sure if he’s sorry he did it or just sorry that he told me. I’m not sure he really gets what a violation this is, and I’m not sure I can forgive or trust him. Any advice?

Unconsenting Adult

Dear Unconsenting,

It’s hard for me to imagine someone so oblivious as to think this would be met with an amused, “Ha ha! Good one!” This person’s judgment is so… uh, so… what’s way worse than “appalling”?

The first thing you have to do is make sure this recording is completely destroyed and that there are no other copies of it or anything else you’ve done together. (I hate to say it, but someone who’s done this once may well have done it before.) Once you are as certain of that as you can be, forgive him or not – that’s up to you – but by no means should you consider dating him again. You’re not sure you can trust him? Why the uncertainty? Obviously, you can’t.

Dear John,

I’m a middle-aged woman, and over the course of the past thirty years or so, I’ve gone from being conventionally religious to fairly hostile toward religion. I have an acquaintance who suffers from a serious chronic illness. She is quite religious, and when I run into her, she will often end our conversation with something like, “Say a prayer for me.” I never know what to say. I feel very bad for this woman—she is a sweet, generous person—but I don’t want to be a hypocrite and I want to be true to my values. What should I say to such a request?


Dear Unbeliever,

Try something along the lines of, “Of course I will.” I know you want to be true to your values, but I’d encourage you to define them a little more broadly. What about compassion? What about providing a bit of comfort to someone who’s suffering? I think those values trump a stubborn, take-no-prisoners commitment to your own beliefs. And by acting compassionately in this situation, you’ll also demonstrate that one need not have any religious beliefs at all to be sensitive and loving.

While in general I think today’s debates about faith are long overdue, the last thing a desperately ill believer needs is a lecture on why she’s fooling herself. (Of course, if you’re lucky enough to run into Christopher Hitchens, feel free to release all that pent-up honesty.)

You may also enjoy:  Dear John: She Doesn’t Want Him …Until She Can’t Have Him

Photo credit: Flickr / tlizana

About John Simpson,

John is a middle-aged family man from Providence. If you learn from your mistakes, he’s brilliant. His column runs regularly on


  1. “Last night, my date left a $5 tip on a $40 check!”

    And it should have been $6, not $10. What’s the issue here–your boyfriend is slightly cheap, or you’re very extravagant?

  2. You are so very wrong to ask someone to go against their beliefs. All this person had to say was my thoughts are with you or something else kind on response. You can have compassion without compromising your own beliefs and values. Would you still feel just as comfortable if you lived in and area where the majority of people were devil worshipers and asked you to say pray to the devil for them?
    . I have the same issue on a daily basis as an atheist living in a very religous area, and would have to compromise my ideas and values many times a day if I did this. However without offending people I manage to show kindness, good morals and compassion in my own way.

    • I agree it was terrible advice to the non-believer. “I’ll keep you in my thoughts” conveys much the same sentiment for the non-believer, without being either a lie or a “lecture on why she’s fooling herself”. A non-committal smile also works, since the non-believers goal isn’t to into detail about her beliefs or challenger her friend’s, but simply to avoid causing tension or discomfort without having to *pretend* to share that faith.
      Even atheists know lying is a poor way to express compassion.

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