QUESTION:

I have a sex buddy. When we started, i was fresh out of a divorce and he was fresh out of a long term relationship... therefore both of weren’t looking for anything serious. Our usual ritual is texting each other only to do with dirty talk, and or making plans to hang out. At first we would see each other about once a week, but now it’s turned into 3-4 times a week.

We hang out, have a drink, maybe smoke some weed, listen to music, talk about everything (politics, world events, stories of our pasts, family, friends, career, everything.) and of course we have amazing sex.I never stay the night. Which I’m fine with because i have a dog and i actually enjoy sleeping alone most nights. Now it’s been over a year we’ve been at it.

Well, I’m sure you’ve guessed it...i am such a girl... i of course have caught some feelings for him.

Is it ridiculous to think and hope he will eventually want me for his girlfriend and pursue me in a different light? I want him to want me for more. I want him to make a move.
How do i handle this without being the needy whiny girl that i don’t want to be? What do i say?

Have some thoughts on this. I'm pretty blunt, as I'm sure you're aware of since you've specifically come to me for this advice. There's nothing wrong with catching feelings for someone you're sleeping with. It happens and it doesn't make you bad or weird for wanting more.

The idea that you're "such a girl" implies that having human feelings is not and OK thing. Being chill is so overrated and blown up - it neglects the very real fact that people are not chill literally at all. The thing is, you're not going to be able to figure out if there is anything there unless you come out and ask about it. Being "chill" is millennial for being too insecure to be real with this guy and yourself. There is nothing chill about that. The idea that someone who "likes the other person less" has all the power is a sick joke we play on ourselves. It leaves little space for authentic communication, which we all deserve with sex partners, no matter how casual or non-casual.

You have to ask him for what you want. If you keep on like this, waiting for him to make you his girlfriend, you will be disappointed. You're playing chicken with your feelings because you're scared of rejection - and trust me, I get it, we all are. But you're going to either get rejected or not get rejected in the end. This is just prolonging the inevitable so you don't have to face scary feelings. It shows maturity and self-awareness to own your feelings. So, own them. Tell him you have feelings for him and you're not into the idea of playing it "cool." Tell him you have respect for him and owe it to both yourself and him to be honest. Tell him if he doesn't feel that way, that's OK, but you want to know now. Because if he doesn't, you can start to move on and heal from this.

Right now, the only person you're playing is yourself. That's a game you will lose.

XOXO Gigi

Order the book: All The F*cking Mistakes: a guide to sex, love, and life.