Help! My Relationship Reminds Me of Dawson's Creek

Allie,

I have a huge problem. I'm in love with my best guy friend. We've been friends since high school, but I've recently started developing feelings for him after he helped me through a rough period in my life. He's all I can think about, and I'm turning down other guys because I can't imagine being with anyone else. Problem is, he has a girlfriend, a bitch who doesn't appreciate him. What I'm asking is, should I tell him I have feelings for him? I'm afraid it will make things between us weird if he doesn't feel the same way, or god forbid, his girlfriend finds out.But I don't think I can live without telling him I love him. Do you think it's worth it? Help! 

Sincerly,

Best Friend Blues

After a couple weeks of answering questions ranging from the kinky (How Can I Get My Boyfriend to Punch Me in the Face?) to the frustrated (Help! My Boyfriend is Trying to Give Me Carpal Tunnel) I'm excited to answer a question that won't make my batshit Southern Baptist relatives want to throw holy water on me. Now on to the advice...

Blues, as I read your letter I couldn't help but think that you may in fact be Taylor Swift. I mean, your predicament screams "I'm a sad girl with an acoustic guitar who has run barefoot through a cornfield multiple times," but don't worry we've all been there. I can't think of one girl I know who has not found herself in the "I'm-in-love-with-my-best-friend" situation, however of all those ladies who have dreamed of playing Joey in their own Dawson's Creek fantasy, I know very few that are actually with their Dawson (they end up with crazy-ass Tom Cruise.)

See, Blues, I put the "male best friend" in the same category as the "bad boy who tries to initiate a three-way with your sister," meaning we all need to like this guy at one point, but it probably isn't going to end well. I believe it fails because when you start banging dating your best friend, you immediately jump straight into serious-relationship land, which you might be a resident of since you have already declared your love for this kid. And dollface, serious-relationship land is not a good place to be three days into dating.

But if you really feel like you can't live without telling him, than I suggest you do just that. Tell him. Don't try to break up his relationship. Don't give him an ultimatum. Don't tell him you have already named your kids. Don't tell him you can suck the cork out of an unopened wine bottle (unless you really can... what a selling point). Just tell him you have developed some feelings and leave it at that. By being honest, but not crazy, you can hopefully avoid any of the post-admittance weirdness.

After you tell him, a few things could happen:

1. He may feel the same.
2. He may feel the same at another time.
3. He may never feel the same.

But at least you will have an answer. And Blues, if he feels the same then he should break up with his girlfriend before anything happens. 

Now go listen to some Taylor Swift and practice uncorking that wine bottle with your mouth. 

XOXO Allie

P.S. If after reading this, you think you're fucked up enough to appear in this blog, write me at notreallyabarista@gmail.com or on Twitter @AllieOopsie. You will remain anonymous!