QUESTION FROM A GREEK TRAGEDY READER: Hi Stephanie, I’ve always felt that you give great advice that cuts through the bullshit even if the incident you’re discussing has never happened to me. Well, here comes the day when I need someone to cut through my bullshit and help me see the light at the end of the tunnel.

I was dating this great boy who I was really into but who turned round four months down the line and told me that he wasn’t happy with the way things were going. The truth is that we were better at being friends than a couple, but I always hoped things would improve. And the fact that we didn’t connect very well resulted in us breaking up three times over those four months, and there being a complete absence of any physical relationship, even though I craved it greatly. So, though I’m not completely bummed about the break up, it’s still difficult to see him around considering we have nearly all our friends in common. And the fact that he broke up with me on the phone when I was traveling on work hurts a bit because it didn’t seem like he respected me enough to tell me to my face. It was a bit rough but I’m trying to get over it, even though he’s just below the surface everywhere I go.

One month later, I think I’m making the same mistake again with another boy who is also my very best friend. He knew everything about the old boy, all the problems we had – and was there for me throughout. The other night when we were hanging out, he kissed me, and one thing led to another, and we ended up in bed together. And it’s been four days of being stuck to each other. I’m not sure whether he’s my rebound or if I really like him. All I can say is that we connect really well and he’s everything the other guy wasn’t. At the same time, I just lost one good friend and can’t stand the thought of losing another if things don’t work out. Which is why I want to run like the wind. But he’s into me and he makes me feel really good about myself, which makes the deciding part even harder. I don’t seem to know anything anymore; I can’t seem to make a decision and stick to it. Would be grateful for any advice you can give me. Or even a knocking on the head. Good guy friends are difficult to come by and I don’t want to lose mine.

Thank you so much, and keep up the awesome posts and photographs!

This was the most telling detail of your missive: “But he’s into me and he makes me feel really good about myself, which makes the deciding part even harder.”

Therein lies your problem. You need to figure out how to make you feel really good about yourself. It’s called self-esteem for a reason. Yes, it’s lovely to receive compliments, to hear how funny you are, how ridiculously hot, kind, whip smart, so damn adorable, but—and it’s a but worth sitting down for—what happens when he stops saying these things? What happens when the newness dwindles? When you begin to feel you’re losing your “hold” over him, that he’s just not as enchanted as he once was? You feel rejected and frustrated, and you become a wee bit psycho. Basically, you take it personally, and if you’re anything like I used to be, you then make his life miserable with all your whining for attention. Bottom line: you need to learn to make you feel really good about you, without him.

The fact is that he says you’re “hot, kind, whip smart, so damn adorable” because he sees these things in you, because you ARE all those things, but you shouldn’t need him to know it or believe it. This is why you’re stuck in Chapter 3. Ahem, chapter 3 of Straight Up And Dirty: Cereal Monogamy (The cereal spelling makes sense in context). You hop-scotch your way through relationships because that’s how you’re holding onto any feelings of worth.

The truth is, it doesn’t matter. What you do with regard to this specific friendship, this specific guy, doesn’t matter when you look at the bigger picture. Until you iron out your own kinks, with whom you get kinky is the last of your problems. And this problem will repeat on you for the rest of your life, rebound to rebound, until you learn to feel good about you without a him.

GOT QUESTIONS? NEED ADVICE?
If you have questions or need advice on anything from where to eat to how to get over the bastard, just email your question to my advice email address. Am I a doctor? I don’t even play one on TV, but people keep asking, so I might as well air it and share it.