After all this cluelessness, I've finally discovered that it helps to become friends with someone before actually dating her. But, there are different levels and types of attractions that exist between friends.
We walk a dangerous line when we attempt to pull off the "friends with benefits" thing.
The "benefits" in that phrase refers to physical intimacy between friends. This is usually a recipe for disaster.
Usually it starts out fine. You are buddies, and you are attracted to one another. You end up making out on a random night, perhaps spending the night together. It feels great: Here you are with someone you can actually stand being with; you're giving in to your attraction and having a great time, no strings attached.
But the rules are all muddled. If you're enjoying making out as "just friends," you're probably going to end up spending a lot of time together. And, usually, this time is spent partying. Because you are friends, why would you actually go out on dates? You end up meeting each other out, drinking, and then heading home together.
Paradise wilts pretty quickly. The rules say that both of you are free to meet others. But as soon as the first one moves on to someone they actually want to date, the friend will feel betrayed, and disrespected. Suddenly, that person who was hanging out with you is dating someone, so what does that make you? "Friends with benefits" has just turned into: "You were never dating material, so you were just a fun fling."
The ironic thing is that, before things went sour, they were so sweet. You both thought you could handle it. And the fact that either of you could meet someone else at any moment is always looming throughout the "benefits" stage.
On the other hand, there's my older sister's friend, who went years being friends with a girl he wanted more with. Through the years they both dated other people, but he remained friends with her and always had a crush on her. Finally, she decided to give it a shot with him and the two hit it off, and now they are married. One of my friends in college was friends with a girl who liked him for three years until they finally got together and had it grow into a serious relationship.
A friend once told me that every guy-girl friendship had some point where at least one of the people was attracted to the other. I've come to learn that this is true most of the time: My best girlfriend in college told my roommates she liked me as more than a friend but not to tell me. Finally, they did end up telling me and I was completely surprised, but I only liked her as a friend at the time.
When we become friends with someone of the opposite sex, that tension usually exists at some level. But in my experience, it seems as though the "friends with benefits" kills the chances of anything serious a lot faster than the slow and steady approach. It's strange how physical elements of relationships make things so much more complicated. The whole "friends with benefits" thing tries to do it in such a way that physical intimacy will not complicate things. But, as time wears on, that facade fades away, and we are left in a strange situation that does not feel natural.
So, being physical requires careful management. But, so often, physical things happen in a flash — most of the time it's better with that spontaneity too. It's a bit of a catch-22, trying to be deliberate about physical activity while trying to keep it spontaneous, emotional, and fun.
Bottom line is that if you do take the plunge into a "friends with benefits" situation, you should be fully prepared for it to net out to nothing of substance, and for the possibility of it disappearing quickly. If you are really into a friend but he or she doesn't seem ready to take a plunge of any sort, it may be a blessing in disguise. This will keep you from getting physical too fast, allow you time to get to know each other, and — if it's meant to be — something of substance will happen when you are both ready.
Have any of you ever had a friends with benefits situation that has turned into something of substance? For those of you who are in something serious that started out as a "friends" thing, did you take it pretty slow? Do you find that you have been attracted to your friends of the opposite sex at some point?