I’ve dated women from all walks of life, from soccer players to math teachers to shoe cobblers. One thing they all had in common was considerable skill in their chosen field. And nice bosoms.

Should you find yourself in a relationship with a deluded artist, it probably didn’t happen by accident. Women love to be praised, and the quickest way to their hearts is through exaggerated and absurdly consistent appraisal of their worth.

Sooner or later, however, their dreams will meet their ambition on the Venn diagram of life, and they will seek out further confirmation from real professionals. After initial rejection, she will presumably come back to you for further encouragement, and now that doubt has set in you’ll have to up the volume of lies.

The sooner you drop the other shoe, the better, the real question is how. If you don’t have the ability to give it to her straight, or fear that your relationship won’t survive, it might actually be more productive to encourage her to seek out that professional advice. Don’t word it like “I think you’re so amazing!”, more like “It doesn’t matter what I think...”, or something to that effect.

Let her know that your opinion doesn’t count for much, in the end, and she might find another path to the cold hard truth.

So, this is a touchy one.  In some ways, it's worse than knowing that your girlfriend has gained weight and feeling obligated to tell her when she asks.  The difference is: in one case, you're crushing her ego, in another, your crushing her lifelong dream. In both cases, I offer you 2 words: Step lightly. And I mean LIGHTLY.

I have never been one to subscribe to the notion that honesty is the best policy, but if your potential life partner has her head in her ass when it comes to career choice, you should probably let her know otherwise you may end up like Charles Foster Kane (Rosebud!).

There are of course layers of complication when telling her the hard truth. I will translate:

1. You're telling her she has bad judgement
2. You're telling her she is talentless
3. You're telling her she now has to renegotiate the way she thought of her life up until now

None of these points are easy to swallow.  She may come back at you on the defensive, so be prepared. "You're a shitty plumber... I run to the bathroom and spit out your cum because it tastes so bad... your mother slept with your best friend."

I mean, really, however you phrase it, it's going to be bad, but if she has any ability to look at herself as a mature woman, she will eventually come around.  And if she doesn't, she wouldn't have made a good life partner anyway. On the bright side, you'll never have to listen to her sing again.