Welcome! Login | Register

Subscribe Now: Free Daily EBlast


Dear John: Dating That’s All in the Family

Tuesday, October 02, 2012


What’s your problem? Write to John at [email protected].


Dear John,

I’m in a weird situation that I’m not sure what to do with. Long story short, I’m a divorced guy in my early 30s. My ex and I don’t have any kids. I wouldn’t describe our divorce as amicable, but it wasn’t crazy hostile, either. There was no infidelity or anything; we just kind of got sick of being together, I guess.
Anyway, we’ve been broken up for about a year. Recently, my ex-wife’s younger sister called me up and asked if I wanted to get together sometime. As in a date. I was pretty stunned, although I’m not sure why – we always got along really great. I’m just not sure this is an okay thing to do. Is there some kind of unwritten rule? Any thoughts?
Ex-Brother-In-Law, Too

Dear Ex,
I don’t know if there’s an unwritten rule, exactly, but there’s definitely an unwritten strong suggestion. The problem here is that there’s no easy way to ascertain the purity of her motives – or your own. Is she genuinely attracted to you, or do you present an irresistible opportunity to hurt a big sister she’s resented for years? And what about you – if she weren’t your ex-wife’s sister, would you be interested? Sometimes the easiest person to lie to is yourself.
If you are both utterly certain that there’s nothing more to this than two adults going out on a date with no other agenda whatsoever, then I think it would be okay (although potentially explosive depending on the personalities of the people involved). But even if you both claimed to have such certainty, I’m not sure I’d believe you. 


Dear John,
My mom, who is very sweet and whom I love dearly, took up painting a few years ago. I bought my first house recently and Mom surprised me with an enormous painting to fill a central space in the house I had mentioned I wasn’t sure what to do with. She came over all excited and insisted on helping me hang it then and there. You can probably guess the problem, and I feel wracked with guilt for even saying it: this painting may be the single ugliest thing I’ve ever seen in my life. And I don’t mean it’s a good painting that isn’t suited to my taste. Mom is a tragically bad painter. To make matters worse, she’s prolific. She has a studio filled with her creations, and I was prompted to write when she mentioned bringing another one over for me! I adore my Mom and I absolutely don’t want to hurt her feelings, but I love my new house and I take decorating it very seriously. I don’t know what to do!
Art Lover, Just Not Hers

Dear Art Lover,
Aw, poor Mom. I’m afraid you’re just going to have to level with her. Tell her you’ve lived with it a while now, and it’s just not working. It doesn’t have to be an indictment of her work; I think it could be presented as an incompatibility between the painting and the location. You could also request a small piece instead and find an unobtrusive spot for it. (And don’t think of it as an aesthetic affront but a reminder that you’re very lucky to have a spirited mom who loves you.)
I have no problem at all with a small lie or gesture to spare someone’s feelings, but you shouldn’t sacrifice your own contentment living under the inescapable glare of a major eyesore. Your mom’s feelings may be a little hurt, but that doesn’t mean you did anything wrong.


Dear John,
I have a good friend who’s unemployed and has been for a while. We work in the same field – in fact, that’s how we met several years ago. Now, I HATE my job – not my career, but where I currently work. My friend recently told me about a job she has a lead on which would be PERFECT for me – and honestly, I think I’d be a better candidate than she would. I really want to interview for that job! Should I go for it?
Help Wanted

Dear Help,
Definitely! With a little luck, you’ll get the job, your friend will lose her house, and you can get that, too!
Come on. I know "It’s business; it’s not personal" excuses a multitude of sins, but not this one. Your friend told you about this job so that you’d be happy for her, not so you’d compete for it. To pursue it now would be contemptible. It’s undoubtedly deeply stressful to hate your job, but I think your misery is clouding your judgment. You should start looking for a new job today; obviously, a better one is out there.
It’s perfectly fine to pursue it as hard as you want if she doesn’t get the offer. But until that time, be glad for your friend and wish her the best. And mean it.


John is a middle-aged family man from Providence. If you learn from your mistakes, he’s brilliant. Write to him at [email protected].

For more Lifestyle coverage, don't miss GoLocalTV, fresh 24/7, here.


Related Articles


Enjoy this post? Share it with others.

Delivered Free Every
Day to Your Inbox