Ask The SEXpert: The Dating Category Dilemma


I find that I put men in two categories when it comes to sexual rendezvous. Category one are the men I meet and decide they are more “hook up” material and therefore I have no qualms around when the hooking up takes place. Category two are the men I deem as possible relationship material and I tend to try and wait before engaging sexually. Since I am a pretty sexual woman I usually struggle with how long to wait so when/if the relationship crashes and burns I’m left thinking, “I should have waited, or waited longer.” I’m starting to wonder if I should wait for “monogamy before sex” with these men in category two, but realize that I would be doing that more as a protection to avoid being hurt again. What other options do I have here? I appreciate the perspective!


Thank you for sending in this question because I feel this is such a classic bipolar mind set among women all over the WORLD! Okay, I am exaggerating a little bit … all over the UNITED STATES!!!

I would have to say your realization that choosing to wait to have sex with the guys in category 2 is more of a protection is pretty astute and most likely dead on! Here is the thing … I know so many individuals that had sex with their long term partner on the first, second or third date. (Myself included!) This is because BOTH individuals were in a space of ‘Why wait? I have strong feelings for you and would rather know sooner rather than later if we are sexually compatible!”

Where it gets tricky is the guilt and self judgment if it doesn’t work out. Or in your words “when/if the relationship crashes and burns”. Because if the relationship DID work out, would the fact that you chose to forego waiting be an issue?

Bottom line is it is a case by case issue! Categorizing is only going to lead to heartache because you are trying to size up a person in a short amount of time and not giving the person (or the potential relationship) a chance.

Keeping your potential suitors to a small number of categories usually causes awkwardness or pain (see image below).

Attractiveness Categories Pic

There are a WHOLE lot of ‘categories’ in between Fuck Buddy and Future Fiance. Are you actually willing to exploring them?

You ask what other options you have … I will keep it simple. There is only ONE option in my mind: “Be radically honest, open to possibilities and fully in the moment with each single person.”

Get to know them. See where it goes on its own. Check in with your intuition regularly. Do what feels right. Try not to label, judge, assume or predict the future with any person or situation. Get rid of the expectations and the categorization.

When you find yourself going there, reel yourself back in and act like you are starting all over again with the goal being “Get to know who this person is. See what they can offer and is that compatible with what you have/want to offer.”

Trust me this is easier said than done but in the end, you will feel like you stayed true to yourself. AND you will actually see these guys for what they are: imperfectly perfect human beings!

Hope this helps!

CS Photoshoot II

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