Well the uncertainty of "will we or won''t we" can hang in the air for a long while and sustain any real (or imagined, or imaged potential) relationship, there comes a time to define the relationship. And as most of us come to realize, a time to move the hell on from the person sucking your life energy and spare thoughts. Some of us will realize this quicker than others, as indicated by this handy dandy pie chart:
Chances are, the person that lets you think its complicated, wants to keep it No Strings Attached, or my other favorite, Friends With Benefits. As I further thought about the complications from getting friendly with friends, I have some thoughts on a great blog post by Thought Catalog, How to Define Your Ambiguous Relationship. Having lived through ambiguity, every text, "Saw Capri suns and thought of you," every ambiguous Facebook post, "You cheated at Candyland," leads you further down a path into ambiguity, and further into the multitude of awkward zones. And before you know it, you're so caught up in this, "What are we, does he care that way about me?"-ness, that you are about one tough friend hiding your phone away from drunk calling with the message, “Arrrrre you muh fuckin’ boyfrien’ or whaaaaaaaat, jesus,” as Joanna from Thought Catalog so articulately put it.
And when you reach that stage, there is a good chance any chance of relationship potential will be zapped by your blooming impatience, like in MV's new show Awkward. The thought catalog outlines these basic steps to defining a relationship (with my comments):
1. Obsess. (Telling everyone, even people you haven't talked to in years, this might be going somewhere. Talking to any male that will listen for advice on "how to handle" him).
2. Brainstorm. (How to run into him, events where you can be in close physical contact).
3. Befriend the person’s friends. (Even if they're hella weird. Attempt to pump them for information).
4. Balk. (Give him some "space" to figure things out").
5. Pull the trigger. (Including asking friend what he thinks of you, only to have said friend get hit on by guy (true story)).
6. Backpedal. (Tell everyone he needs space. Tell yourself he is an idiot, but so lovable).
7. Build resentment.(Over-analyze everything he says in the opposite direction. There's no way he went to the gym 5 times this week and couldn't send you a text. Really hate him. Watch movies with endings where everyone is miserable, and laugh while doing so).
8. Take another pass. (Tell him he is an asshole for even talking to you in the first place. Reprimand him for breaking your trust. Then say you will give him one last chance).
9. Cross your fingers. (Go out for a weekend with the girls. Pump the Beyonce!)
And here you have a chart version of the love/relationship cycle (assuming you actually make it past the DTR chat stage):
And my advice to avoid DTR, be upfront and honest. It's all too easy to play your cards close to the vest, not let him know if you clearly like him, just in case he doesn't feel the same. But being honest early on (don't be the girl he goes to to talk about other girls), and finding out where he stands will save much ambiguity and heartache.
So now your at home, trying to enjoy a low key Saturday night, watching as your cell phone inbox is inundated with texts that are written in a language where "jkaxbjk" is a word. All you can decipher is that this dude is begging you to come over because he "really likes you right now." 
