SilentOne's advice column

I'm an 29 year old guy.
I'll always do my best to give well considered and sincere advice - give me your best shot. P.S. Don't be afraid to ask me private questions, I rarely spend a lot of time answering non-private questions.

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Alrighty where to start? Well I've known my best female friend for about a year. I always try to do the sweet things such as getting her candy, carrying her books, even going shopping with her. Even at school people always make rumors about us going out, but there are times where I feel like she has interest in me and times where I don't feel anything. She doesn't know that I like her. My question is should I confess to her or if not what should I do?

M/16

Hi,
Well, the first thing I've got to answer with is a question;
What would happen if you didn't tell her?
The answer to that one is pretty much always "the same thing as always", which sounds like it has been "nothing" so far.
It depends if you're willing to risk rejection from her, and possibly the consequence that you wouldn't be good friends with her anymore. It's tricky to stay good friends with someone you really like, but who doesn't want anything to happen.

There are two ways you can approach the problem;
Sneaky or blatant.

Sneaky;
Gradually increase the amount of time you try to spend with her. Drop subtle hints about what you like about her. Compliment her on her hair if she changes it. Basically, from what it sounds like, you already spend a lot of time with her. The only difference between that, and being her boyfriend is a degree of intimacy, and a little more time. Once you put in the 'more time' part, it is quite possible she will notice your extra effort, and either shrug you off kindly by telling you she's not interested, or add the intimacy.

Blatant;
Ask her out for dinner, or some occasion which is difficult to mistake as a casual "friendly" event. Or even more blatantly, decide what you're going to say (make it shortish), and just tell her you like her.

Personally, I tend to the sneaky side of things, as it usually limits public fallout, and allows a lot more diplomacy in the case that she doesn't really like you.

p.s. You don't necessarily need to be buying her lots of things. Buying too much stuff for people does a few things- makes the receiver feel pressured or guilty for not giving something in return (whether or not the something is a relationship, or gifts back), and can also be a bad way to waste a lot of money on people who ultimately don't care for you (i.e. this is how you attract people who don't like you for yourself, but like you for your gifts)

p.p.s. I've found a saying to be fairly true, I don't regret the things that I have done half as much as the things I did not do, when I had the chance to.

-K

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(Rating: 5) Thanks, very helpful advice :)

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