Can you date your female friend?

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It’s more difficult to move from friends to dating than it is to just start with dating and move to friends after it’s clear it won’t work out.

People seem to have two categories they place other people in. Sexual / romantic partners and everyone else. I don’t care for this kind of categorization so in theory I would have no problem with it.

The problem is that it’s not just me. How the other person sees you is just as important as how you see them. You may be open to a romantic liaison with your attractive friend, but she may not be open to one with you.

Even if they are open to it, there’s the problem of actually changing the context of your interaction. If you’re used to interacting in a certain way with them, to suddenly change things about that so as to move it closer to flirting / romance, can feel not like you’re gaining a romantic partner, but losing a friend. Especially if the relationship doesn’t work out. People in general prize their friends more than the people they date, so subconsciously we’re going to resist changing contexts like this.

Two people can lust after each other for years and never take the steps they need to get what they really want out of each other. It happens often enough they make movies out of it. In these movies, generally something outside the context of the friendship will force them to reevaluate their lives and how they want to spend it.

Dramatic things like that rarely ever happen in real life, and I can see how attempting to create something like that could be seen as manipulative. I can also see how difficult it would be to change your relationship slowly.

The best example in fiction I’ve ever seen of something like this happening is The Office. Jim and Pam started as friends and eventually became lovers and got married. But it took a long time. And they never really ‘dated’. They just took up with one another once all the obstacles were out of the way.

If you’re willing to put in the time and effort, it might be rewarded. Of course, it might not be. She might not be attracted to you. She might not be willing to potentially sacrifice her friendship with you for the momentary bliss of romance.