Dear Tequila,

Your advice is so funny! I want to know what you think about friends becoming more than friends. I have had a friend tell me recently they have feelings for me. At the same time I can't help but have feelings of my own for another friend of mine. What should you do to let a friend down easily? Should you ever take a chance into turning a friend into a boyfriend? I hope when I'm as old as you that I will know the answers but in the meantime help me Obi Wan Tequila you're my only hope ________________________________________________________________________

Dear Anakin,

Like the force, this has the potential to be either light or dark. There is no right or wrong answer to this question. Some people will argue that the quest for true love is worth any risk, including the loss of a few Jedi Knights. Whereas others would rather face a loveless future than risk losing a close friend to the Sith. Alright, I'm done with the Star Wars references. I hope that's enough to appease your inner nerd because I'm about to overdose on social awkwardness.

In all seriousness, there have been an equal amount of successes and failures in this endeavor. So much so, that even myself, as wise and OLD as I am (thanks for pointing that out btw asshole) can't even tell you with certainty what you should do...perhaps it's the dementia? What I can tell you is what I know just from reading your letter.

First, your letter tells me that you are not attracted to the one friend who is attracted to you. That's a not a crime. You can't help how you feel. However, to answer your question of how do you let him down gently...well... here's the thing…you don't. It's not possible. Too often people fool themselves into thinking that one way of breaking up with someone or telling someone you're not interested, is better than another. That's a fallacy. It doesn't matter how you do it or say it, they're going to feel just as shitty and disappointed. The death of a loved one doesn't hurt any more or less if they die at twenty-five or seventy-five. They still died. You still grieve the same. The when and how is insignificant. The same is ultimately true with rejection.

The concept of "letting them down gently" is not the sweet and selfless notion that people would like to think. In reality, it's rather selfish. Letting someone down "gently" has nothing to do with them and everything to do with you. You're not trying to make them feel better at all. You're trying to make yourself feel less guilty and better about disappointing them and hurting their feelings. Ultimately, more often than not, this just ends up hurting them more.

Why? Well, let's think of the ways one typically lets someone down "gently" and how it's actually perceived by the rejected:
a) "I don't want to ruin our friendship." = "I'm really interested in you too, but I'm scared."
b) "I'm not really looking for a relationship right now." = "when I'm finally ready for a relationship, I'll want to be with you."
c) "I really care about you but..." = "I may fall in love with you eventually but I'm not there yet."

Do you see where I'm going with this? If working in retail has taught me anything, it's that people hear what they WANT to hear. They interpret your words in a way that best suits their desires. In your attempt to reduce their hurt and your guilt, you actually end up giving them false hope. So, rather than moving on and potentially finding love and happiness with someone else, they cling to the notion that someday it will happen between you. You cause more harm than good.

Picture your one friends attraction for you as an out of control hot air balloon and your friend its only passenger. If you leave it to float in the breeze and slowly deflate, it eventually makes its way to the ground. However, it takes a long time and your friend is pretty much trapped there, floating in limbo, without food and water and could potentially starve or dehydrate before it lands. BUT….if you shoot the balloon down, sure your friend may break a few bones on the landing but at least he knows where he stands...or will eventually stand once the leg heals. And believe it or not, the wounds caused by your tragic rejection will heal. You're not THAT special.

Be honest. Be sincere. Be clear. Be blunt. "I'm not attracted to you that way. If you're hoping that one day we will be a couple, I need for you to understand that I don't feel that way about you. I value our friendship but to be fair to you, I need to be honest. If being just my friend is not enough for you, I would understand if you would rather not be friends at all."

I know what you're thinking, "Tequila, you are such a bitch." And...Yes, yes I am…but sometimes you need to be. It might sound harsh, but at least it sounds clear. It leaves no room for miscommunication. He's going to leave the conversation feeling shot down and wounded but not confused and that, my young friend, is the whole point. By using what I've said, or some variation thereof, you leave him with some semblance of control. This is extremely important because he's probably going to feel pretty vulnerable. You've robbed him of the power to steer the direction of your romantic future but in exchange, you leave the future of your platonic friendship completely in his hands. Which is a more than fair trade, since he clearly has a deeper investment in you than you do in him.

Let him determine if being just your friend is a situation he can live with and be comfortable with and if it's not, be prepared to let the friendship go. Just like he cant convince you to give him a chance romantically, its not fair for you to try to convince him to stay in a friendship that is awkward and/or heartbreaking for him.

Now onto the second portion of your question....Should friends become boyfriends?

Duh! OF COURSE! Assuming they're hot and queer. If they're hot and hetero...GURL PLEAZ! Don't kid yourself.

If the friend you have your eye on meets all the requirements, then ultimately it's up to you to decided if the chance of finding a love connection is worth the risk of losing a good friendship. Clearly, that was a decision your one friend had to weigh carefully, and it's not going to turn out so great for him, now is it?

You need to be prepared for the same rejection that your showing your first friend. And, if I may be honest, I think THAT'S what really has you hesitant. You're afraid to be rejected. Karma's a bitch but she's also poetic and when you send something as negative as rejection out into the universe, you inevitably receive it back.

But what if it's not this time? What if the friend you like feels the exact same way about you? Are you willing to live your life not knowing? Of all the things I've experienced in my life so far, the things I regret most, are the chances I didn't take. If you don't play the lottery, you're never going to win.

Friendships grow and change throughout the years. Sometimes they grow stronger, sometimes they grow apart and sometimes they become romantic. But every time is a roll of the dice. If life is a gamble, then love is a crap-shoot. Place your bets or leave the casino.

And, if you're still unsure, just have a threesome. This way all three of you are somewhat happy, at least for a brief moment. Unless, of course, the friend you like finds you and your other friend sexually hideous. In which case, I suggest heavy amounts of liquor.

For him, not you.