My last post on relationships / cheating / communication was the most popular in the last five posts or so.  I know, you want juicy stuff as opposed to pictures of fantastic food (though I maintain that tasty food is one the great joys in this life.)  I think you’ll find that communication (and a lack thereof) remains a major theme in many of these posts as it directly affects the success of probably 90% of human social interaction.

Anyway, as you’ve read a few times now I’ve been single for right about eight years now (I’m literally within a week or so of the anniversary of the breakup.)  Post relationship I spent a lot of time focusing on myself and rebuilding, and then a few years later I started looking around for somebody who could be “the one”.  Well, the bad news is I haven’t found her yet.  The good news is I’ve gotten pretty good at this bachelor thing.  I’ve had a fair amount of forward movement professionally,  I’m improving my financial status daily, I’ve got some pretty strong bonds with friends of mine personally and (sometimes related) I’ve generally been pretty successful sexually (As in, women have regularly found me desirable enough to share themselves with me in that manner…)  So if I can’t have the one, this is a pretty awesome close second.

What blows my mind when I talk about this with some people is why they (or more often their “partners”) really suck at this casual sex thing.  It’s like they took something they saw in a movie and expected real life to be like that (thanks Hollywood.)  While I understand the male need to “alpha” (ugh) and the female desire to not be a “slut” (really ugh) you need to understand that those terms, and even those concepts are fucking ridiculous ideas created by insecure morons who were likely trying to manipulate you in order to keep you “in your place”.  Men must be physical, unrelenting, dominant, stupid cave men, and women must be weak, blindly dedicated, subservient nurturers.  Obviously… NO.    Now don’t get me wrong, this sort of role-play in the bedroom as playtime is all fine and well and healthy if that’s what you’re into, but as a standard of operation in the real world it’s narrow-minded and limiting for both genders.

So, whether you’re in-between serious relationships, getting a little on the side (legitimately.. or not..), indefinitely single by choice or you’re like me and are holding out for “the one”, here’s a few guideline “Dos and Do Nots” that have worked very well for me and I think are pretty universal (but is nowhere CLOSE to a complete list.)

First, DO:

1. Be Honest.  If there is one thing that will ruin a potentially good situation and make it ugly, it’s you spouting a bunch of bullshit.  It’s not “the game”.  It’s real adult life, so act like it.  Be straight up about what you want (and even how you want it…) in the beginning, even if it’s tough to let somebody who was hoping for more down.  It’s true, this might damage your chances of getting busy in the short term, but think of it as an investment.  The worst thing that happens is they respect you for being straight up with them and move on.  Sometimes though, they become friends, and sometimes that comes with benefits.  More than a few times I’ve been told I’m a good choice for that sort of thing because they know where I stand and don’t have to worry about complications.  Honesty keeps it simple.  When things are simple we can do our thing and get on with our lives.

2. Be Respectful.  This is huge.  Did you know that when somebody feels like you respect them, they are much more likely to let you see them naked?  It’s not rocket science.  This means eliminating words like “slut, whore, etc” from your dictionary as those are basically misogynistic double standards created to shame women (and albeit far less often, men.)  Newsflash: If you make people feel bad about being sexual, they are a lot less likely to be sexual with you.  This is ironic because people will often put down somebody’s sexual activity/history with others and then turn around and try to make something happen. You’re not going to make them feel okay about hooking up with you if you berate them for hooking up with others.

3. Be A Friend.  So a big part of functioning as a friend with benefits, is (wait for it) being an actual friend.  I’m not saying you need to pour your soul out to them and spend a bunch of time with them, but communicate, relate and hang out without any expectations periodically.  You’ll find some people become important to you and others stay very casual, but as long as there’s not false expectations, things stay pretty light.  When the benefits DO kick in, it depends on the person, but they might be wanting to play every time they see you anyway.  Sometimes that really IS the core of your “friendship” (gee darn.)  But the danger is in assuming.  So be cool, be a friend, keep it light, and fun.  The more fun and flirty (if accepted / appropriate) you are, the more likely at some point you’ll hit that moment when you know something is about to go down.

4. Be Patient.  If there is any one major secret to my sexual success, it is that I know when to be patient.  Often times people are not in the mindset / position to hook up (or, maybe just not hook up with you) when you first meet.  But that doesn’t mean they won’t always be. If you were honest (see step 1) and told them what you were about in regards to them, and then you were respectful (see step 2) then you will probably have some level of interaction with them on a friends basis (see step 3.)  So long as you’re not overbearing about it, if they thought of you sexually at some point in the past, odds are somewhere deep down it crosses their mind from time to time IF you’ve been fun and easy to be around.  Then if you’re lucky, they’ll let you know when they feel like acting on those thoughts.

5. Be Smart.  Sometimes I tell my friends stories of people I know that have literally slept with over a hundred people.  To this day they are healthy and happy and obviously know how to attract attention.  On the flip side I have personally witnessed somebody in a Frat House years ago who had been with probably five people in their life at most, hook up with three different people consecutively in a drunken rampage that didn’t appear to include protection.  That, to me, is a stupid, sad story.  (For the record, there was no visible rape involved… this person was literally seeking the people out and they were very happy to receive them…)  Point being, both sound pretty scary right?  Yes and no. There’s something to be said about numbers, as number of partners can indeed affect your chances of contracting an STI.  But the point of my example is that the first person knows what they are doing, is protected and communicates openly with their partners.  The second… not so much (obviously.)  Who’s the bigger risk for you to hook up with?  Call me traditional (see that whole friendship thing) but I kinda like to get to know my partners and even moreso communicate with them.  Does this mean I haven’t hooked up randomly at a party before…?  Well, no.  But I was protected and though I left the next morning, I left my information (which she was super surprised by), we became friends, had some great sex and her and I have hooked up a few times in between her boyfriends since then. Regardless my point is:  Learn about your potential partner by communicating with them, use protection, get tested.  It’s all fun and games until you start screwing around with somebody’s health (including your own.)

Next: DO NOT:

1. Have expectations.  This isn’t just about friends with benefits, this is about dating in general.  Numerous times have my friends told me the person they were out with made some offhanded remarks like “Oh man you’re going to be so amazing when we finally sleep together…”  What?!  I can’t even make up something that ridiculous.  Needless to say that sort of attitude is a very quick way to screw your chances (no pun intended…) and possibly damage the friendship.  Having expectations also leads to inevitable disappointment if they happen to not feel like hooking up at that point.  This can cause you act out in stupid ways and damage your chances in the future too.  So play it cool, show your interest (casually!) and don’t count on something happening the first, second or any time.  To be honest I’m not certain of the science behind it but I very often end up getting busy when I am pretty sure something won’t happen going into the evening for whatever reason.  It’s nice to be surprised!

2. Try too hard.  I’ve done it, you’ve done it, we’ve all gotten to the point where we got really really excited about a potential date/hookup/girlfriend/boyfriend/etc.  We got super nervous, put on too much smelly stuff, forced the conversation and likely drank entirely too much in the process.  Where did it get you?  Lot’s of places, but not in bed with the person you wanted.  Both genders have a sense for when the other is trying too hard, and it comes off as desperation, which in most cases is a huge turn-off.  Sometimes they may have totally planned to hook up with you, and the sort of erratic behavior that comes from nervousness and irritating passive-aggressive pushiness convinces them it might be a bad idea.  It’s good to seem interested, but keep your cool because desperation will scare most people off.    

3. Judge.  I’m going to be straight with you here, your opportunities for casual sexual encounters will come from all kinds of unexpected places (I mean.. they have websites for this stuff.. and no, for the record, I’ve never used Ashley Madison.)  Anyway, the point is regardless of circumstance, judging the other person for their choices will (obviously) screw up any chance you have of hooking up with them.  I’m not just talking about those fooling around on their spouse either.  You want to take the moral high ground?  That’s your business.  But otherwise people are in totally honest, open, polyamorous or even mostly monogamous relationships that might, for some reason with to include you and/or legitimately see you outside of it.  Maybe the idea of multiple people weirds you out? Well that’s fine!  But judging others about their activities outside of their involvement with you is not.  At the very least, it’s really hypocritical being that you’re trying to make yourself a part of those decisions.

4. Be Possessive.  This happens all the time, and women get the bad rap for it despite the fact then men very often get emotionally attached and fall into this trap.  “No Strings Attached” means no strings attached. (Like “no means no” with more words.)  Do not come into a situation claiming your ability to remain unattached and keep it casual and then expect it to magically change (thanks again Hollywood.)  If you begin to feel differently, you’re gonna have to talk about it.  The whole point of the benefits behind casual sex is that it’s casual.  You can get together, have a good time, maybe grab a bite to eat, and get on with your lives without having to take it with you.  It’s like going to the gym: you might be sore from it the next day, but otherwise it has no effect on your outside life other than making you feel better about things.  I realize that for some the emotional separation is difficult, and it’s easy to attach to somebody that is both a good friend and fantastic in the sack, but once you start feeling like you can tell them not to see anyone else, or go on dates, or even how often they need to see you, you’ve crossed the line from casual to trying to control them, and that’s not okay.  If you find this happening you need to talk about it, and it may be best if you downgrade to regular friendship.  If by chance you’re both wanting to take it to the next level?  That’s wonderful!  But very rare, so don’t hold your breath.

If you keep you head in the right place and your emotions in check, you can have a really great time and take care of those urges without hurting anyone.  I think that’s the best thing: when everyone knows what they want, they get it, and everyone walks away happy.  But this is only going to happen if you’re willing to be honest and communicate about your situations.

I could go on about this forever, I even considered dividing it into two posts.  But I liked how it flowed, and I felt it was related enough it warranted a long post.  Last week was the longest post yet until this one and it was very popular so perhaps you don’t mind a lot of words as long as I can keep it interesting (or maybe just sexy.)  Regardless, expect more on this, we’re just getting started.