Miss Information: So many women, so few decision-making skills.

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Dear Miss Information,

I’ve noticed that you’re pretty vehemently against extracurricular activities. I happen to be in a relationship with a hubby who is into being a cuckold. He even gets me ready for dates and vets potential partners. I was completely faithful for thirteen years (we’ve been married for eighteen) and probably wouldn’t have done anything like this without his prompting. I’ve had a couple of affairs, both of which were with married guys who didn’t tell their wives. In an ideal world, the wives would be cool with this but I haven’t found another couple where the wife wants the hubby to sleep around, swingers excluded. Hubby has the option to go out as well, but he doesn’t seem interested in taking it — he’s more interested in my adventures and supporting me in my "sexual athleticism." What would you do in my situation? Have affairs knowing that my hubby is happy, or keep vows that he no longer wants? — Having Fun with Life’s Lemonade

Dear Having Fun,

I think you may have misunderstood me. The only extracurricular activities I disapprove of are mandatory fundraisers ("Hello, sir or ma’am. Would you like to buy an oversized novelty tin of popcorn?") and the Young Republicans Club.

I’m all for whatever relationship arrangement works best for both partners. It’s screwing around behind someone’s back that I don’t like. So when you read my response to the husband who wants to see an escort because his sex life is boring or the girlfriend who hits the gay clubs because she can’t confess her pussy cravings to her boyfriend, I want you to keep that in mind. I may be a white girl from the Mitten State, but I’m not so square that I disapprove of all alternative lifestyles.

Keep having your affairs and cuckolding your husband. You’ll probably sound the preachy alarm again, but Miss Info would love it if you stuck to men with informed and willing partners. Games are more fun when all the players know they’re playing, whether it’s a gang bang or touch football (sometimes one and the same). If you’re having a hard time rustling up dates, you may want to try Ultimate Cuckold (warning: really bad 1996-style design), Cuckold Place, or Craigslist. Are any of my readers into this? Where did you dig up your third-party stud?

Dear Miss Information,

So, the planets must be aligning or something because suddenly, out of nowhere, I’ve had a string of minor hookups with different girls.  All of them have expressed interest in dating, and I’m attracted to each of them, but this surplus of options is causing me angst.  I’m not built to be a player, and the thought of juggling all these girls makes me feel like I’m being disingenuous. I don’t want to hurt anyone or fuck them over.  At the same time I’m well aware that dating opportunities in New York often evaporate as quickly as they appear.  My friends say to pursue everything.  What does social protocol dictate, and how can I best navigate this lovely minefield? — Not Hugh Hefner

Dear Not Hugh Hefner,

Before you do anything, you first have to figure out what you want. A girlfriend? A casual lay? Several girlfriends? A wife? Along those same lines, figure out the reasoning behind it. Did you just end it with a long-term girlfriend and want to wait before you get serious again? Are you feeling a little pathetic pouring your heart out to your dog and want a real girlfriend to curl up on your lap while you watch 24?

Generally speaking, the more serious your relationship goals, the fewer girls you’ll want to be seeing at one time. I agree with your friends that you don’t have to winnow it down right away. Get to know these women a little better and have some fun. But be aware that most women (and men) who are looking for a steady commitment aren’t keen on being one of many. They may be cool with an open-ended arrangement early on, but eventually you’ll have to make a choice.

As for questions of etiquette and logistics, honesty is the only way to go. All these lovelies should know you’re not interested in dating anyone exclusively, preferably before the naked thing happens. In-person is best, but do it over the phone or via email if you have to. The most important thing is that you make the information known.

Expect varying reactions. Everyone has their own ideas of how dating should be conducted. If you do your best to be forthright and considerate with all parties involved, there shouldn’t be a problem. However, if one or more of the women share the same name, neighborhood or employer, forget everything I just said and run to another city.

Dear Miss Information,

I’m good friends with most of my exes. One is even my best friend. Here’s the problem: Every relationship I’m in follows this pattern: I fall head over heels for a guy, who seems into me but soon says he just wants to be friends. And it’s not an excuse — he really does want to be friends.  This switch can happen before or after anything physical happens. And while I’m happy to have the guy friends I already have, I don’t really need any more — which makes me reluctant to date at all. So how do I get around that "switch" moment? I want a boyfriend, dammit, not more boy-friends. — I Have Enough Friends

Dear I Have Enough Friends,

Either you’re going after guys who aren’t genuinely interested in you or your dating skills are lacking. Those are the only two explanations that I can think of. Let’s address the former first and the latter last, after which I will congratulate myself on having finally mastered the correct meaning of these terms after years of struggling with the dictionary.

When a guy’s not interested, I Have Enough Friends, he’ll usually let you know. Long lags between phone calls, lame emails that don’t really say anything, unreturned texts and infrequent, unpredictable communications, that pesky "girlfriend" person who keeps showing up — these are all signs. Because you’re head over heels, you will choose to ignore these signs and see only that Snookums Wookums Pandaface is responding to your advances. This creates a relationship that’s unstable and one-sided. You wind up as Velma when you want to be Daphne.

The easiest way to prevent this switch from playing out? Stop calling. Two things will happen: 1. He’ll realize you’re a hot commodity and up the wooing OR 2. He’ll pleasantly vanish from your life. No uncomfortable conversation on why you have no interest in watching him play Wii with his boys. Win-win, baby.

On to your dating chops. First instinct is that you’re coming off too aggressive. I don’t want to go with that theory because it’s based on very limited information, and it’s bullshit how girls are always being told they’re too aggressive. ("What do you mean you called him? Didn’t you see what they said on Tyra? How dare you!" It’s like the 1950’s all over again.)

Since you’re such good friends with your exes, why not lube ’em up with alcohol and talk to them one-on-one. See what you can glean from them regarding the way you act on dates. What was it about you that they liked or disliked? How did they feel in the beginning, middle and end of the relationship? What was the turning point (a particular date, conversation, etc.) that led them to believe you two were better off in a state of not-fucking? I’m sure some of your pals will give softball answers or evade the questions, but there may be a few pieces of viable info you can use to prevent the next switch from happening.

Good luck, and remember that one advantage of guy friends is that they hang out with other guys. A smart hussy will work it from all the angles.

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