The process of transitioning from being friends to being more than friends is the third most difficult challenge known to modern man. (1. how to establish universal health care in the US. 2. How to bring peace about in the Middle East, and 3. How to tell your best guy friend that you actually wish he was your boyfriend. 4. opening plastic packaging for certain electronic devised.)

Every seven seconds some girl somewhere starts crying because she doesn’t know how to tell that guy she has feelings for him (note: US stat).  It’s a god-damned mess. Should she even do it? What if she does it and he doesn’t have feelings for her, obviously the friendship is ruined?What if she doesn’t and he does have feelings for her and they just never end up together because both of them are too chicken to say something? Isn’t there just a way to figure this out indirectly so there’s no slash low risk and everyone ends up happy?

Allow me to Bounty extra quilted this shit:

Yes.
It doesn’t matter.
Right, exactly.
And No.

Of course there’s more.

Blanket statement that appears as opinion but is fact, fact:

If you have very strong romantic feelings for one of your close male friends you should either make those feelings clear or stop being such good friends. I support the former in most cases, but do as you please.

Why?

Because of another blanket statement that seems like an opinion but is actually 100% truth:

If you have very strong romantic feelings for one of your close male friends and don’t make them clear or stop being such good friends, the friendship – as it is – will eventually end anyway.

Here’s why:

A friendship in which one party is in love with the other is not a friendship — it’s a unique social situation where one person is engaged in friendship while the other is engaged in a life mission to figure out if he/she loves them back. As such that person (a girl for example’s sake) often behaves less like a true friend and more like an actress – an actress cast in the role of this guy’s girlfriend.  Does said female actually want this person as a friend in her life? Yes. Would she continue to want him if she was 100% certain he didn’t and would never love her back? Debatable, but probably no.

That’s what makes this “friendship” ripe for destruction. Half of its members don’t want it like it is and have ultimate designs to change it. As such they frequently find themselves doing things that are designed to appear friendly in nature but are actually plots to figure out what’s really going on inside his head. Such as: let me bring him around my guy friends from college so he can see that I treat him differently than I treat him and realize maybe I like like him. Or – let me invite that guy I met at the bar last week to his party so I can see if he acts jealous… Or the common – let me invite him to go Flea Market shopping so he can see me in my adorable Flea Market shopping outfit slash mode and realize that he really does love me…and then he’ll just tell me. Yes, it’s as exhausting as it sounds. And no, it can’t go on like that forever. That’s where the destruction part comes in, and it comes in one of three forms.

1. You crack. Alcohol plus years of denied feelings can/will/often does lead to slurred confessions, black-out “moves”, and/or you telling his roommate that you love him and begging for advice. I’ve never seen all three go down, but I wouldn’t put it past someone.
2. He starts dating someone who isn’t you. (Hopefully this happens before you crack…)
3. He loves you back and somehow this just becomes very clear and then you start dating, and it’s as it always should have been.

Here’s why no matter which of those happen, it’s for the best.

1a. No it is not easy to recover from drunk-confessing that you love someone. Yes things will take some time to be back to normal, if they ever go back to normal. But this is good because they 100% needed to change. You cannot and should not remain as close as you were to this person! It’s crazy and self destructive and preventing you from being with someone with whom you’ll have a reciprocated relationship. So method: negative. Effects: awkward. End result: correct. Sorry.

2a. Yes this will hurt, but like the above, it will get you where you need to be – out of a co-dependent relationship with a friend you want to date. To reiterate: friends you want to date aren’t friends, they’re projects.

3a. I’ve heard this happens. I believe it’s possible. I haven’t experienced it directly or indirectly, but if you find yourself in this lucky situation – fuck you.

Moral of the story. You need to change this relationship. You can change it with a heart-felt letter that holds the option of response, “if you feel the same way, let me know. If you don’t, let’s spend 6-8 months not speaking. Best, Jessie”. You can change it with a drunken confession to his best friend that gets back to him — and then awkwardly back to you. Or you can let it die and slowly back your way out of the friendship (sometimes if the writing is on the wall – and your friend finally convince you of this… this is best decision). But the situation will eventually run its course and whatever happens between you two further down the road might have a lot to do with how you handle the crossroads.

And yes, I know the title of this post is “how” to go from friends to more.  That was a device to draw you in.  If I titled it, “why going from friends to more is really, really difficult and carries very few examples of success but you should still get it over with and tell him” you’d probably x this out and return to examining what girls have recently written on his Facebook wall…