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Deciding whether or not to have sex with someone on a date can be a tricky thing.

Based on my past experiences, I want to say to tell yourself to wait until the 3rd date or later…but really it’s up to you, your mood, the chemistry, etc. and you shouldn’t feel pressure one way or another. Have something ready to say if your feel the pressure but don’t feel the desire. I learned the sentence beginning with “My personal policy is….” (Fill in the blank) to wait until I know someone better, or whatever your new policy is at that moment in time, works great. Just prepare yourself ahead of time because it’s not always easy to think of how to handle it when it’s right there – staring you in the face. Especially if you are out of dating practice.

I was always concerned about hurting the other person’s feelings…until I made some mistakes and toughened up. But then again, you do learn pretty quickly from having sex with someone if they are worth another date. I guess it would depend on the purpose of your dating. I had sex with one guy because he hadn’t dated since his wife died. He was a nice guy. It was “charity” sex. I decided to boost his ego and give him back some of his self-confidence. I knew already I didn’t want to see him again but thought what the heck. He wasn’t a good lay either. I let him down easy and made excuses about not being clear on what I really wanted in a relationship at that moment in time – which wasn’t entirely an untruth. I really wasn’t clear yet on my actual dating objectives.

Another guy I slept with right away I thought had potential (Note – never a good idea…I married someone because I thought they had “potential” – bad, bad idea!). He was shocked when I broke it off the next day and actually got quite angry and aggressive…he thought our 4 hour roll in the hay meant some sort of “ownership rights” of my person I guess. I was trying to be nice but when he wouldn’t let it go and was shocked I didn’t think he was a God because we had sex for so many hours, I finally told him a stiff cock and a willingness to use it didn’t necessarily equate to good sex. I’m not 100% sure what he had to say in response, because it was in a foreign language…but I’m pretty sure I was able to properly translate the words “crazy whore”.

Pity sex…different from charity sex…never again. I won’t bore you with all the gory details, but trust me – don’t do it. A man who you feel pity for needs to spend time with his own hand before venturing back out into the real world with real people.

If you are dating to find a “real” relationship, go slow. Make sure you match up on enough levels to make it worth the try. If you are dating just to have fun and pass the time, then it’s a case by case decision. Whatever you do – keep yourself in check. Dinner, dancing, sex does not mean you should start making up a future life in your head and picking a china pattern! Slow your roll and appreciate it for whatever it is…right now…at this moment.

If you are “dating” for a “fuckbuddy” relationship, you need to be clear about that from the first moment. I also recommend talking about sex a lot before meeting for the purpose of sex. Even then you may have to “sift some sand” before you find the right one for that role. One guy I interacted with over the course of a long time talked a good game, but when it came down to it was the most boring fuck ever. Then he had the nerve to say “that was pretty good for vanilla sex”. I moved on quickly from him.

One night stands are okay if that is what you want. No strings, no obligation, no awkward interactions later…down and dirty sex with a stranger, who shall remain one – by your choice.  I do believe most women aren’t built for that…we tend to want to “know” someone or “feel some kind of connection”. If you do decide to have a one night stand, either purposefully or accidentally, don’t kick your own ass over it. It’s done – move on. And for goodness sake don’t let them guilt you into thinking there is obligation for another evening. Be very honest…say “Thank you for the one night stand” or “Thank you for fucking my brains out – I needed that – have a nice life”.

 A fuckbuddy is someone with whom you are sexually compatible, can have sex with whenever you are in the mood and both available, no strings, no awkward “morning afters”, no explanations…just good sex when you need it with someone you have already had sex with and you know enough of their good moves to keep you coming back. It’s a beautiful thing. But again, most women aren’t built for that…so if you’re not, don’t do it. It was so completely perfect for me during one stage in my life. I worked 12-15 hours a day, didn’t have the time or emotional energy for a “relationship” and all that word implies…and it was just wonderful, blissfully fulfilling sex as many times a week as I needed it. I would still have him today (or someone just like him) had I not accidentally gotten into a real relationship with someone else. I had to break it off and see where this accidental relationship was going because he wasn’t really on board with me having a fuck buddy on the side.

If you are going to date multiple people for multiple purposes, it requires you compartmentalize your feelings. This works for some of us. For others it does not. If it doesn’t work for you…then don’t do it. I also recommend if you are dating multiple people, be honest about it. I scared off a few men with my honesty, but that’s okay – they probably weren’t right for me anyway. The one that didn’t get scared off but laughed and asked questions instead, is the one I’m still with 4 years later. He also meets my needs on all levels so I no longer need an assortment of people for different things (companionship, fun, mental challenge, hot sex, etc.). He showed up when I became very clear on what I wanted in a partner “some day” and stopped searching for it.

One thing I’m very sure of is don’t have sex with someone out of some misguided feeling of obligation to because they went on a date with you, or bought dinner, or whatever…if you decide to have sex it’s for you. Own it. Tell yourself – yes I am entitled to have sex if I want it. No guilt. No remorse. Buy your own damn dinner. Maybe even buy his.

I have opinions about married sex too (surprise). I will probably address that in a future blog post.