Simon Says, Volume 1


With his smooth English manners and stylish wit, Simon is “spot on” when it comes to giving good advice to the readers of Singular magazine.


Alessandro Guerriero/ 123RF Photo

Weight Gaining Girlfriend

Dear Simon,

A woman I started dating last spring was in great shape when we met, but over the summer, put on about 30 pounds. I don’t want to be superficial, but it’s grossing me out! Plus, I’m concerned she’s just going to keep gaining and gaining. When we go out to eat, she seems oblivious to her food choices and orders things like fried foods and rich desserts. It’s like she’s clueless about what she’s doing to her body. She’s a really great person, but this weight gain has killed my desire to be intimate with her. I know “the talk” is coming. I don’t want to just run away as I do like her. Help! — Less-is-more Larry

Dear, dear, Larry. Less is more? Come on. This is America, boy. There is no such thing as less is more. More is more! Supersize me! Seriously though, your girlfriend may appear to be oblivious about her food intake, there is no way she is clueless about what she’s doing to her body. Every time she takes a backward glance in the mirror, she knows. So if you really like this girl, “the talk” is not what you need. “The talk” is the end of all relationships. In fact, the mere mention of it makes me wonder whether you really do like this girl, or are just looking for an excuse to end it. If you do, then stay away from the whole diet side of the equation and focus on exercise. Exercise not only burns calories, but also raises self-esteem so she’ll be less likely to take solace in food. I’m told horizontal jogging is particularly effective.

Foot Fetish or Fancy Friend?

Dear Simon,

I know this is going to sound like something from an old Sex in the City rerun, but my friend Tamara has what I consider an over-the-top shoe fetish. Her swooning and incredibly lavish spending on footwear — not to mention her talking about it constantly — really bugs me. There are so many other issues of more importance in the world, and we only talk about shoes. I feel this anger boiling up inside me each time she mentions a sale or her newest acquisition. Am I being petty? — Shoe Enough Eleanor

I think you are being a bit of a Rigby. I mean, I don’t have a shoe fetish myself, but the sight of long legs in the right pair of pumps ranks up there with a curve of breasts in La Perla’s finest. Still, I have the feeling that this is not really about shoes at all. Reading between the lines, I think it’s likely there is an income disparity between the two of you and Tamara’s lavish spending simply highlights the inequality. Every time she tells you about her latest purchase, you may feel that she is flaunting her wealth and trying to belittle you and so you respond with anger. It would be better for you to accept that life has its disparities, but also recognize your own worth. A true friend is a rare and valuable treasure, and Tamara is bringing you her shoes in search of your approval because she wants to be your friend. So next time, instead of getting upset, just imagine that you are a deity and she is laying the shoes at your feet in worship. You’ll soon develop an appreciation for them that will make Tamara so happy she’ll start to genuinely worship you.

Perils of Puppy Love

Dear Simon,

The teenage daughter of my longtime friend is smitten with a boy whom I know my friend disapproves of. This girl, whom I love and have known for her entire life, is reaching out to me to talk, get advice and just vent. She’s a good kid, unlikely to do anything too stupid, but now I feel torn between being loyal to my friend and being loyal to her daughter. How much am I obligated to tell my friend about what’s going on in her daughter’s life? Or is it better to not violate her daughter’s trust, so in case something major does happen, she’ll know she can come to me about it? — Doubly Devoted Dora

I think you have pretty much answered your own question here. You know that your friend’s daughter is “a good kid,” and you trust her not to “do anything too stupid.” In those circumstances, it’s better not to violate her trust. While her mother’s disapproval may well be justified, unless the boy in question is dangerous, it should be ignored. Your friend’s daughter is an adolescent. She needs to assert her independence and learn to navigate the shoals of love on her own. One of the best ways for her to do that is to fall in love with a boy her mother frowns on. That’s the point. However, there’s no need for you to worry. If it is a normal adolescent relationship, it will follow a Darwinian course: love… heartbreak… despair… chocolate. All you need to do is keep an eye on her until that last stage, and then show up with a box of Lindt truffles. She’ll be fine.

Copyright © Simon Says / 2015 Singular Communications, LLC.

Have a question for Simon that you’d like to see answered in Singular magazine? You can reach him at

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