Miss Information: How can I find a woman to satisfy my complicated fantasy?

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Miss Information: How can I find a woman to satisfy my complicated fantasy?

Have a question? Email Letters may be edited for length, content and clarity.


Dear Miss Information,

I'm a newly married female in my mid-twenties. I brought a lot of emotional baggage to the relationship. I was taken advantage of sexually from a young age and much more that I won't get into. I've worked through all of that in therapy, but it's a daily struggle to be a better person than my history would have me be. My husband, on the other hand, has had a mentally healthy and drama-free life: good relationships, a solid family, and the ability to go abroad and pursue his dreams. He's adjusting to marriage quite naturally, while my predisposition is to over-worry. Prior to getting married, I felt that I had gotten to a very healthy place. Now, faced with his happy, carefree, and fulfilling past, I find myself filled with rage, regret, and bitterness. It's detracting from my enjoyment of our otherwise fantastic marriage.  

Question one: obviously you're going to suggest therapy, which I agree I should get back into, but do you have any other advice for making peace with my past, and not feeling so bitter when faced with his good fortune? 

Question two: my husband and I believe in complete transparency. We have joint access to everything, including computers and email. I don't know if he looks at my account. I do, however, occasionally look at his. I'm not entirely sure whether he realizes I do that or not, and I feel bad. Part of it is my inability to trust. I was cheated on in the past and was raised to believe people aren't trustworthy. Is this arrangement bad? Am I horrible for taking advantage of it to reaffirm what an awesome and reliable guy he is? 

Question three: I'm currently unemployed, so I'm stuck a the house quite a bit. Idiot that I am, I began looking through the photos on my husband's computer. It started off benign: he's taken a lot of cool trips to places I wish I could go and I was mostly just curious to see them. But then I came across some photos of him and his ex. We had decided (actually, he had suggested) that we both get rid of all photos from past relationships that aren't part of some greater context (a group of friends, or in front of a monument, for example) I'm sure he didn't intentionally keep them, so I took it upon myself to delete then. Then I began scrolling through all 9,000 photos, looking for exes. I started deleting those photos, too. Eventually, I wound up deleting some of the group/contextual pictures, until, as far as I could tell, all traces of his exes were gone.

I immediately was hit with remorse over having destroyed his property. I'm fairly certain that, had I asked, he would have deleted the pictures on his own. I know what I did was wrong and a betrayal. What do I do now? Do I fess up and risk losing his trust? Do I hope he never notices? Do I try to recover the photos? I know I'll never do anything like this again. I feel like a fraud, and like I don't deserve him. I don't want to mess up my marriage. — Wish I Were Better

Dear Wish I Were Better, 

Question one: yes, go back to therapy. Marriage, although a happy event, is a major life stressor. Not going in for a touch-up would be like getting preggo and then waiting for your water to break before getting pre-natal care. In the meantime, he may have the happier past, but you have the better [fill in the blank]. Whatever that is, find it and be proud of it. Don't ever assume that the status quo is always going to be what it is. Resist the urge to mentally build up your husband at the expense of your own self-esteem. 

Question two: yes, the email arrangement is bad. Grown adults should not have access to every bit and byte of each other's personal data. Not only does it invite conflict, it's unhealthy and unromantic. You are not business partners or parent and child. A little privacy strengthens your identity as an independent person — something important to a strong marriage — and preserves sexual mystery. You're not horrible for taking advantage of the situation, but do your marriage a favor and suggest you each get your own logins and passwords. 

Question three: try to recover the photos using an outside party or with the help of tech-savvy friend. If you can, excellent. If you can't, fess up and apologize your ass off. Either way, insist on getting separate logins and never do it again.

Good luck, and remember that nothing short of a lobotomy is going to remove past or future thoughts of other women from your husband's head. Once you surrender and realize that this is a war you'll never (ever!) win, you may find some peace in that. You may also ask yourself why you're even fighting that war in the first place. Clearly you're the winner — those women are in his past, and you're the one who's married to him.

Dear Miss Information,

I'm a man with a fantasy about being spanked by an attractive female teacher or CEO-type, any age, in her classroom or office. I placed ads on Craigslist but did not receive any responses. Any ideas on how I can make this happen in real life, no strings attached? Like you said in an earlier column, sometimes asking people about this stuff "isn't like asking for extra ketchup at the drive-through." — Bad Student in the Back Row

Dear Bad Student in the Back Row, 

Happy to help. First, a quick math lesson: 

  • Take the number of people currently trolling the Internet for casual sex
  • Subtract those that are men, men masquerading as women, and/or paid professionals
  • Subtract those that don't find you attractive
  • Subtract those that do find you attractive but don't meet your requirements
  • Finally, subtract those that do find you attractive and meet your requirements but aren't willing to risk losing their jobs over a total stranger

The numbers, Bad Student in the Back Row? Not in your favor. In Fantasy World, it seems a relatively simple task to find some hot executive, make an afternoon trip over to her office, get your ass beat, and go on about your day. After all, aren't we living in the age of sexual enlightenment? But not so fast there. Before they'll engage in any kind of stranger sex, most people (if they have don't want to wind up in garbage bags in the trunk of someone's 1992 Camry) are going to put certain safety measures in place. Meeting in a neutral location is a common one. Unfortunately, a non-neutral location is a key component of your fantasy.  

Even if you got to know one other first, and then met for an after-hours workplace fuck later on in the non-relationship, it's still a mindblowingly bad idea. I can't even imagine what would happen if I got caught screwing around in one of my office's pristine white conference rooms, and I work in the depraved world of advertising. Can you imagine if I were an educator? Not only would I lose my job, I'd have that Hasselbeck weasel slagging me on The View and the morning-zoo shows making dirty jokes at my expense. No, thank you. 

Here's what you do: run two ads simultaneously. One talks about your fetish. One's just looking for a vanilla lay. Give it some time, try some different websites, and see which performs better. My guess is the more general one will result in more hits, but you might as well keep the specific one up, just in case you get lucky.

When you do find someone to meet, don't ask for the whole filthy enchilada right away. Flirt. Talk dirty. Share something a little bit kinky, then kinkier, and so on. Let her conversational cues be the guide. Who knows, maybe you'll build up enough trust that she'll actually let you come over to her office for some punishment. Until then, remember that fantasy is about illusion. You don't need an 100% authentic setting. Hit up IKEA and the hardware store. Buy a small blackboard, a long wooden ruler, and a couple of cheap desks and chairs. Trust me: if you both really commit to the role-play, your dick won't know the difference.