my dating rules sexylittleideas
or Dating: Expectations and Obligations

I and Jill from are writing about our sex/dating entitlements/obligations. Dating is below, originally posted by Jill on her site here, and you can find our Sex Rambling on my site, here.

What are your dating rules?


I am not expecting to fuck you.

Of course, I would like to fuck you (let’s get that right out of the way). You are a beautiful, intelligent woman; if not we wouldn’t be here betwixt candles and Cabernet. But if it doesn’t happen, whether tonight or ever, I am fine with that. That’s one of the benefits of being a polyamorous man. I am a heterosexual, polyamorous man.

I thought I’d get that out of the way with you right at the beginning too. Since one of the things I am expecting from you is effusive honesty, it’s only fair that I give you the same. I think we’re both entitled to not only being straight with each other but forthcoming.

Have an olive. They’re locally-grown.

I appreciate you coming alone. You’d be surprised how many women bring a girlfriend or roommate the first few times. Not because they’re scared of me, I’m a skinny guy, and this is a public place, but because they’re afraid of running out of things to say.

When we’re not alone, I don’t get to know you or even her but some other third entity that is created when you and her are together. When we’re a group, you never do or say what you want or what she wants but what this third imaginary friend made up of you-and-her wants. And I’m not dating both of you. So I appreciate you coming alone.

The sweetbread is dipped in olive oil, it’s a perfect chaser to the olives, try some.

At the end of the evening here, I don’t mind paying or just kissing the bill Dutch-style. What I do mind is being expected to pay it as if it were my duty, the toll required for the divine blessing of your company. I plan on treating you like royalty, but if you act like royalty, that will only ruin it.

But if I offer, you’re welcome to accept.

You’re also welcome to offer, and I may or may not accept. But let’s not get ahead of ourselves.

I guess the last thing I am expecting from this is that we both start with open minds. As the time passes, our minds may gradually and irreversibly close around one of many possibilities like Venus flytraps deciding they’re going to make a meal of that particularly fly. But let’s take time picking our fly. I may have heard things about you and you about me. But we’re here so we can make up our minds for ourselves. And that requires that they not be made up already.

I mean, about you as a person, and also about you with me and our adventure together. I cleaned my apartment before coming here, but I’d be just as happy to sleep alone in it. Being prepared for something isn’t necessarily feeling entitled to it. In fact, I would say that being unprepared entitles you and binds you more to one certain thing.

If, when I picked you up, you told your roommate you would be home by midnight, you will feel entitled to me getting you home by midnight. If you didn’t tell her anything, I may still get you home by midnight or 1 AM, but at least we started with an open mind. See what I mean?

And now that you have me honest, open-minded, and all to yourself, let’s see what happens.


I feel entitled to date the gender of my preference without judgement. I’m not so feminist that I’ve given up men, and I’m not such a fan of cock that I can’t imagine sex without it. I’m entitled to go back and forth as I please without explaining myself to anyone.

I feel entitled to date single people close to my age. Oh, how I wish this were a given. I am beyond sick of married men twice my age responding to my Craigslist ads, completely ignoring the fact that they are offering me absolutely nothing other than the opportunity to fulfill their fantasies. I also receive the occasional email from a married couple hoping to use me to spice up their sex life; these email always focus on their (actually usually just one partner’s) desires and how I can play a starring role — provided I fit into their very specific and inflexible fantasy.

I feel entitled to converse about more than just sex. In fact, I feel entitled to not even mention sex on the first date or two.

I feel entitled to a partner who is just as invested as I am. Few things feel worse than being emotionally invested in someone who just doesn’t care. It’s not their fault — feelings can’t be forced — but it does not make for a good relationship. Let’s not drag things out if there’s nothing there.

I feel entitled to make choices about my body, including choices about my personal appearance. Everyone has their preferences, but I’m the one who lives in this body and I’m not going to change the way I look to try to meet someone else’s ideal. I totally will wear those pants you like though.

I feel entitled to intelligent partners. I would have so much more sex if I couldn’t spell.

I feel entitled to open discussion. Obviously it’s inappropriate to talk about marriage on a first date or to have the “Where is the relationship going?” talk too soon or too often, but I do feel entitled to talk about my feelings and I expect my partners to communicate openly. No surprises.

I feel entitled to an equitable contribution to the relationship from my partner. Dating and relationships take work and I expect my partner to make an effort. That doesn’t mean we both do the same things, but it does mean that we both have the same goals.

I feel obligated to pay for at least half of the first date. I do not want to send mixed signals or to create feelings of entitlement in my date, regardless of other contributions (such as driving to their city rather than meeting halfway) I may have made.

I feel obligated to accept my dates and try not be judgmental. Even when they show up wearing stained and torn clothing or with prominently missing teeth or whining that the restaurant only offered Gorgonzola dressing rather than bleu cheese.

I feel obligated to keep the peace. I love to argue, but I feel obligated to hold back on a first date — even when my date is asking questions about where my boss when to school and implying that he knows more about my field than my (very qualified) boss, let alone condescending to acknowledge that I might know a little something about it myself.

I feel obligated to keep the conversation going. It can be difficult to make conversation with a near stranger, but I try to be prepared and attentive. Sitting in awkward silence is a great way to end a date.

I feel obligated to have both a plan and an opinion. I like to meet my dates with ideas about how we could spend our time and a willingness to speak up as we work things out. Few things are worse than trying to get to know someone who thinks everything is “fine” and refuses to take part in the decision making process or even share an opinion.

I feel obligated to show an interest. If I’m having fun and enjoying the other person, I feel obligated to share that. Dating is hard enough without second-guessing everything, and a little communication goes a long way.

We’d love to hear what you think — tell us about your obligations and what you feel entitled to when on a date.