Simon Says Advice Column for Singles

Simon Says, Volume 3


Our stylish English gentleman is back with candid advice for readers’ questions on sexual compatibility, too many cats and wine country gaffs.

Simon Says Advice Column for Singles
Alessandro Guerriero /123RF Photo

Dear Simon,

After dating a man for several months, we finally slept together. I’ve been single for a long time; he was divorced after a long marriage. I was the first woman he’s had sex with since his wife. The first time we did it, he didn’t touch me intimately at all with his hands or mouth — other than mouth-to-mouth kissing — and then he went straight into intercourse.

When it happened the same way the second time, I decided there was no way we would be sexually compatible. When I tried to break it off with him, he pressed me for a reason and I told him how I felt — that I felt like he was turned off by “girl parts” since he didn’t want to touch me there. He denied it and apologized profusely (to the point where it was ridiculous) and begged to have another chance. I suggested he buy Kim Cattrall’s book, Satisfaction, The Art of the Female Orgasm, which is very explicit about what to do and where. I thought his masculine pride would be irrevocably damaged and that would be the end of it — instead, he got the book, read it and was eager to show off his new skills. I agreed to give it a shot and it was a huge improvement, but the whole experience has left me uninterested and I still want to break it off. I feel bad because he tried so hard and even got the book — but now I still want to dump him. Why do I feel this way? —Fickle Pickle

Poor Fickle, you are in a pickle! After a long drought, the monsoon finally arrives, but instead of the downpour you were hoping for, all you get is drizzle. But enough of the silly metaphors, let’s talk about sex. From what you tell me, I think the pair of you both handled that side of your relationship well. The sex might have started badly, but you were able to communicate your dissatisfaction, and your boyfriend was able to overcome his inhibitions and improve his performance. If the result was a “huge improvement” in such a short time, then you should be able to enjoy a healthy physical relationship without too much further trouble. 

But your problem is not the actual sex, it’s that you found the whole experience awkward and embarrassing, and perhaps a little humiliating. To make things worse, you discovered that your boyfriend was not the lover you were hoping for, which lowered your opinion of him to such a degree that now you want to end the affair. That’s understandable, but before you do so, I suggest you take a step back and examine the rest of your relationship. Given that you were dating for several months before you slept together, I would venture that you found this man had many good qualities before you discovered his flaws. If that is the case, you should give him a second chance.

Dear Simon,

My hot new girlfriend wants us to take a four-day trip to Sonoma to visit the wineries and tasting rooms. She considers herself to be quite the connoisseur. I, on the other hand, am strictly a beer-on-tap kind of guy. I feel like I’m going to look like a fool next to all those snooty wine-tasting types. Can you give me some hints on how to keep from looking like I grew up in a trailer park? — Beer-loving Bart

 If you are going up to Sonoma soon, you won’t have time to learn anything substantial about wine tasting, so you’ll have to bluff your way through. To that end, I suggest you watch the movie Sideways. Love it or hate it, it’s the only pop culture reference you’ll need, and someone is bound to mention it. Watch it on Netflix to learn the body language so you’ll look like you know what you are doing. If you swirl the glass and sip like a pro, you may never need to even speak. But if you do have to express an opinion, just use words that genuinely describe the flavor you experience. Whether that be “grassy” and “citrusy” (whites) or “berries” and “tobacco” (reds) doesn’t really matter. Taste is subjective. Yours is valid. 

Dear Simon,

I have been doing the online dating thing with mixed results. Finally, it seems I have “met” a guy I find interesting. I say “met” in quotes because so far, it’s been a long-distance romance. We’re making plans to get together at a halfway point and are excited about finally meeting face-to-face. My problem is that I have always prided myself on being very up-front and honest about everything. Even my online profile is really me. This is the dilemma: In the pictures on my profile, one is of me and my cat. But I actually have four cats. In my talks with my long-distance flame, I haven’t avoided the subject of my cats (much) — but have avoided mentioning the number of cats. I have been careful to emphasize my love for animals, cats in general, but haven’t talked much about mine. He hasn’t asked either and he doesn’t have pets of his own. I feel like I’m concealing this and I don’t know how he’s going to feel about multiple felines. I’m feeling uncomfortable and insecure. How and when should I bring this up to him? —Cat Woman

I really don’t think you need to worry about your feline felonies. If the guy you are going to meet has seen the picture on your profile, and cats were going to be an issue, you’d know by now. Still, if you feel really uncomfortable about it, the simple solution is to mention it before you set off to meet him. Just tell him you have four cats, and see what his response is. 

On a more serious note, what I am uncomfortable with is the idea that you are making plans to travel to a far-off place for some face-to-face with a guy you’ve never met.  And I don’t need to put quotes around that: never met. That is so dumb it’s dangerous. For while you might pride yourself on being up-front and honest about everything, when it comes to Internet dating, you have absolutely no evidence that your long-distance flame is the same way. In this case, you really need to exercise a little discretion. Forget the cats and worry about your own personal safety. 

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 Simon at


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