How many dates would you go on before you fucked a guy…. if you already fucked the guy? And a side bar.

My closest friend in the world is starting to date a guy that he met 3 years ago on Craigslist. They met because my friend was looking to have some hot fun, and his Latino ass fit the bill.

Fast forward three years and the meet again… this time on Grindr.

Round two.

There was still a strong sexual undertone in the conversation about them getting together. They talked about hanging out and watching Netflix, and talked about maybe having a drink. Horny-ness was acknowledged and plans were made.

They met, watched some TV, and then decided to lay down and “take a nap” while watching a movie. One film led to another. They cuddled the entire time… holding each other, holding hands, his lips pressed to his shoulder.

(Who knows about the other guy but my friend definitely felt something.)

They’re about to go on their third date… prior to which my friend reached out to ask how long you should wait to fuck a guy your dating, even tho you fucked before?!

This time things seemed different. It felt like these two very sexual individuals had realized that they had more between them than they past imagined.

The answer is complicated.

Assuming an answer exists.

Today, this 4th of July, my motivational moment is about time and how the layering of experiences is ultimately what leads us to be who we are, and to have what we have… as individuals, as partners, as family, and as friends. Time is the key ingredient to our lives because it is the vessel that allows our actions to equate all that we are.

My advice to my friend is… as long as he and you are engaging and planning to spend time together than the best thing to be done is to enjoy the moments and look forward to planning the next.

As for the sex, who knows? But, time will tell.


Sidebar —

It occurs to me that there is another issue at hand here. One that I think needs to be raised and discussed. Perhaps I will lend more detail to it at a future time, but allow me to touch on it briefly now.

In the world of online dating new behaviors are emerging. Specifically, we are having more connectivity to one and other, and for that reason there has been a marked increase in casual sex.

People are enjoying these new sexual freedoms and opportunities.


There seems to be some difficulty transitioning between the lifestyle of sexual freedom, to the lifestyle of dating and partnership. One thing my friend is concerned with is how he and his guy might be able to discuss how one and other indulged in the digital dating lifestyle when they were single. He is also concerned about deciding what indulgences may or may not continue should he and this guy couple up. As he puts it… “When you were claiming to want a 3-way 3 years ago…. how do you take it from that to ‘husband and wife’ ?”

Just something to chew on.



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