I've been dating my boyfriend for years, and he's always had dreams of becoming famous with his garage band from high school. I feel like it's time for him to give up and make music a side project. How can I approach this topic?
It's hard. You want someone to follow their passion and their dreams. If he's not ready to give that stuff up, I think you have to let him go. He's just going to feel like an unfulfilled broken person with crushed dreams. If you have starving twins in your fourth floor walk-up studio apartment, maybe there are some discussions you need to have, but if you're just two hipsters and he's doing that, you've got to let it roll.

My girlfriend and I have a generally good relationship, but I have a bit of a wandering eye. I want to focus on her and try to be monogamous. Any tips for a happy sex life with just one woman?
It doesn't sound like you're ready for that. You need to look into yourself and decide. You could talk to her about it, but that's probably not going to happen. I think everyone has a wandering eye to an extent — it's in our DNA to look at other people and think they're hot. But whether you act on it is another story.

Why are musicians better in bed?
If you're a guitar player, you have strong hands, so I suppose for massages or stimulation that would be nice. But it could potentially be worse, unless you're into dating narcissists. 

Are you a narcissist?
I don't think so, but I have some tendencies. I don't know if it's being a narcissist or being a first-born male from 1966.

So you were pampered and given blowjobs your whole life?
Metaphorical blowjobs.

The guy I'm dating has a weird fetish. He likes to wear my clothes, like skirts and heels. Do I have to indulge this strange behavior?
It doesn't seem particularly out there to me. I wouldn't call it vanilla, but I'd call it vanilla with a little bit of chocolate syrup. So yeah, indulge him. Women's underwear seems like it would be comfortable. I'd wear it if I had no other clean laundry.

I'm obsessed with the lead guitarist in a local band. What can I do to get him to notice me, besides being in the front row of all his shows? Is that too obvious?
Yeah, that's probably not going to work. It's going to put you down a few notches in his psychological hierarchy. The best way is to hang around where they sell their merch and try to talk to him. 

What should I say?
Just wear something hot and look really sexy, and then it doesn't really matter what you say.

So if my boobs are out I don't have to be witty or interesting?
I don't think any three words you say are going to be the answer. The way to open the door to meet someone is to hope that he thinks you're cute first.