The hardest part is that society will tell you “It can’t be done.” So it becomes a self-fulfilling prophecy.

The sex and friendship part is not difficult. Swimming against the social current of “what everybody knows it true” is much, much more difficult. Especially since “Samantha” said differently.

You will get a lot of advice on how and how not to manage such relationships from people who have absolutely no experience with anything more than serial monogamy, at most. If you want to explore further, ignore such people.

It’s possible to have a relationship with fluid boundaries that is healthy, honest and works out well for both over the long term. The key is to be clear that your friendship is what brought you together, way more important than the benefits, and is to be to be nurtured…and really mean it. As long as you have an understanding that you both must honestly share where you are at frequently, the friendship can last and grow from the intimacy that develops from deep affection and sex. If you end up being super close afterwards, it takes tons of maturity and respect for each other and your respective mates to not give the physical attraction so much attention anymore. If the sex was really, really good for both, anyway. That can be done, though.

If you think you can be friends afterwards, go for it, Dad’s. Just realize that there is risk involved and be willing to deal with any “fall out” sensitively and kindly. If love develops, it might not lead to the life that you or she imagined, but really, isn’t that a good thing? Life rarely follows our plans or imagined path anyhow.

It’s too bad that so many want life exactly as they want it, with no adjustments for life’s surprises (I’m referring to your ex). I’ve done that and now I’m reading your blog because I’ve recently reconnected with someone I once loved and he’s a single dad. I’m single, no kids and I used to be strongly opposed to becoming a step mom, but my feelings for this person are strong enough for me to consider adjusting my preconceptions.

As a single gal, I really should check out the South Bay given all that I hear about the man to woman ratio.

Some of the girl (space) friends I have right now are just friends, but I am attracted to them. Why not all in one with them? Some of them are single moms who have compartmentalized their lives, and don’t want to bring a man into it. Others are long time friends who maybe don’t want to be a step mom, or don’t feel the chemistry with me for a deeper relationship, or I don’t feel the chemistry with them.

I am looking for that “all in one” thing. There are more single men than single women in Silicon Valley, so it might take longer to manifest here than in other places.