Rules of Engagement Part II: Dating Is Dating

You’ve found that perfect someone or someones with whom to have sex (on the internet, as I suggested in Rules of Engagement Part I) and now you’re ready to meet them in person! This whole process can be fun or frustrating, so I’m going to break it into manageable chunks. Going on dates with other couples or with singles should be treated just like regular dating. If you enter this stage with that mindset, trust me, you’ll come out much happier.


Scheduling is the hardest part of meeting people to decide if you want to have sex with them and they want to have sex with you. There will always be work issues and childcare issues and curfew issues. You also have to consider whether your first meeting is just to get to know the other person/people, or if there will be play on the first date. Here are some things to keep in mind when you’re making dates:

  • Suggest at least three different dates that are at least three to five days in the future. This will give the other party time to check their schedule and make any necessary arrangements. Weekends are typically better, but not everyone works a 9 to 5 job
  • Have a backup plan. Once a primary date is chosen, also agree upon a backup date in case the first one falls through. People always get sick, family emergencies happen, sitters cancel. If you have a backup plan in place with the other party already it won’t seem as awful when they cancel on the first date
  • Arrange your own childcare well in advance, and have a plan B in case your childcare falls through so you don’t have to back out at the last minute
  • Mutually decide upon a location. Public meetings can feel safer, especially if you have the other party come to a restaurant or coffee shop with which you are familiar. Feeling like you are on “your own turf” adds confidence to your demeanor, and confidence is sexy. It is absolutely okay to go to someone’s home or have them come to your home if everyone feels comfortable. Remember that being in someone’s home can add unintentional pressure to mess around on the first date simply because there is a bed under the same roof
  • Decide on a time. Meet early enough so that if the chemistry is right, you don’t have to cut the date short because people have to call it a night. Weekend afternoons are wonderful
  • Decide on your own boundaries. If you go into a meeting expecting sex you will be disappointed and it will cause stress between you and your partner. Remember, this is like a normal date. If you are both okay with messing around on the first date, great! Don’t expect the other party to be. If you aren’t ready for that and you want to take it slow, also great! Don’t let the other party pressure you into something for which you’re not ready. So I will just say…
  • Go with the flow. We like to schedule dates and times in a way that leaves the possibility for a little first date action and/or a way to abort the date if things just aren’t meshing. You can’t plan what will happen, only your own actions. So set a time, meet the person or people, and see what happens!

What to Wear

Again, treat this as a normal date. It’s a special occasion and you want to make a good impression on the people that you’re meeting. We always dress nicely for dates, keeping the location in mind.

  • DO dress to impress. A nice dress or skirt for the ladies and slacks and a collared shirt for the men is all it takes to look like you give a damn
  • DO NOT just wear jeans and tee shirts and tennis shoes. I don’t care if you’re really casual people. Showing up for a date in casual clothes tells other people you don’t care. I don’t want to hear any of that, “I wanted to be true to my self and show you who I really am,” crap either. If you’re a casual gal who isn’t girly, I’m sure you have a decent blouse or sweater to throw over those jeans with some flats or something. Gentlemen, you own a polo or something that has a collar… I know you do. Wear it ironically if you must
  • DO wear nice underwear. You don’t have to go full on Frederick’s of Hollywood under there, just wear something without holes. You probably aren’t going to mess around on the first date, but wearing decent undies makes you feel sexy and exciting. It will help you be sexy and exciting to the other people, whether they will ever see your underwear or not
  • DO NOT wear club clothes. Over-dressing is just as bad as under-dressing. Ladies, that tiny little tube dress just makes other women hate you… not want you, and if you have to rock Spanx underneath you won’t feel sexy. Trust me. Gentlemen, your shiny shirt frightens us… a dress shirt is awesome on a man when it is tasteful and classy
  • DO consider whether there will be walking. This one is really directed at the women. You know you love those three inch heels that pinch your toes a bit. If there will be walking of any sort during this meeting, consider your footwear carefully
  • DO wear condoms. Not the entire time, of course, but if things get frisky… wrap that shit

What to Talk About

Believe it or not, you probably won’t talk about sex during your date. No matter how naughty your e-mail exchange leading up to said date, people tend to take a big dose of vanilla extract right before meeting people in person. Since we’re still treating this as a real, live date and not just a sex hook-up there are some topics you might want to avoid and some that you’ll be dying to talk about.

  • Avoid politics and religion at all costs. Really, do I have to elaborate on this one?
  • Movies, music, and TV shows will save your life. Pop culture bullshit makes for one hell of an ice breaker. Find something you have in common and you’ll feel more comfortable
  • It’s okay to talk about your job. But don’t only talk about your job. Work often brings up negative discussion topics and bitching. You are not sexy when you are bitching about your boss
  • Be prepared to talk about your relationship. But don’t only  talk about your relationship. The couples that are overly into each other are super annoying. We get it. You love each other and she’s the bees knees. Definitely talk about how you met. Definitely talk about how you became interested in threesomes, foursomes, and moresomes
  • Only talk about your kids if the other people have kids. I mean it! People without kids do not care about your kids so shut up. Once you start you will not be able to stop
  • Don’t be creepy. Don’t tell the other party you’ve been fantasizing about them when you two have sex and that you can’t wait to see them naked, blah blah blah. That stuff is entirely acceptable once you’ve started having sex with said party, but not before. Ew. Use your filters, people
  • Be honest… always. But also be polite. Avoid swearing excessively or telling off-colour jokes. We’re trying to make a good impression. Be on your best date behavior
  • Bring it up. Don’t wait around for the other party to bring up the fact that you are sizing one another up for sex. It is okay to talk about wacky sex so long as you are mature and considerate about it. You may not be interested in them, or they may not be interested in you… either way it’s the reason you’re meeting so it is totally okay to bring it up

Abort! Abort!

It’s not all sunshine and roses in the world of wacky sex and you might just need to get the fuck out! Did the other party send you old pictures and completely misrepresent themselves? Is there some strange hygiene problem that has icked you out? Can you just not deal with their donkey laugh or their wandering lazy eye? Are they just awful?

It’s cool. I got you. Here’s what you do:

  1. Establish an “Out” story early on. If you have kids, indicate one is sick and that you might have to cut things short. Otherwise any sick family member will do. You should then submit yourself to about 40 minutes of the date, and then fake a text message and excuse yourself to make a call. Make sure your partner is in on the ruse
  2. Use a fake calling app like Fake-Call Me. You can set it up on a trip to the restroom and have your emergency from there
  3. Or stick it out. Have your coffee or meal or drink and then part ways. You’re already out, may as well make the best of it
  4. You can figure it out. Regardless of your escape route… always wait one to two days, then send a polite e-mail thanking the other party for meeting and then state that you simply aren’t a match. Wish them luck in their search

You Place Or Ours?

If everything goes swimmingly and it seems like there is a little action to be had on this, your very first date, you may want to move the date to somewhere more private. Go with your gut. If it feels right it feels right. If it doesn’t and you aren’t ready, don’t put yourselves into a situation where you feel pressured. If there is chemistry, that chemistry can wait until the next get together. We’ve messed around with people on the first date, and also waited until the second or third. You may want to take a few minutes alone with your partner to discuss this. It’s acceptable to excuse yourselves and speak privately for a few moments in this situation. No one will think ill of you for making decision that feel right for you and yours.

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Lions, & Tigers, & Self Care

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Chris Martin Writes

One couple's wacky, multi-partner sex adventures and quest for poly love.


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