Dear Sasha, For 2 years we’ve been on and off but never dating because he always made excuses (dating stresses me out, I’m not good at it, I’m not planning on staying in the city). For the past 6 months we’ve been sleeping together (secretly because I know my friends would tell me I’m just going to get hurt). I was ok with it, because I figured something with him was better than nothing. We agreed that it would be exclusive and if anything changed we would let the other person know. Fast forward to an Xmas party, where my best friend announces that W (my guy) has a new girl! I wanted to barf. He was there but not making eye contact with me. The next morning he comes over and says it was just 2 dates and he didn’t think my best friend was going to announce it like that. He says he doesn’t know what it is with us, but he feels like something is missing.  The next weekend he invites me over for dinner with the preface that “she’s” going to be there. I go, she’s lovely, and then I have a breakdown on my best friend’s couch afterwards and tell her everything. She tells me to talk to him and let him know how hurt I am. I do, in a long email. We talk and agree to go on as friends. The new girl goes away over the holidays. All is good (albeit I'm heartbroken) until NYE, when we’re at the same party and we end up making out. The next day I go to his house and we fool around. Later, in a text I ask why he kisses me if he doesn’t like me. He says he does like me and he doesn’t know why it doesn’t feel like it works.   I have no idea what’s going on with them, but I feel so awful. I wait for his texts and feel like sh-t if I don’t hear from him. I just don’t know how to move past this. He’s one of my best friends and I see him all the time.  I know he’s “not into me” yet he strings me along and flirts enough just to keep me always wanting more. I just feel so stuck. Any advice would be greatly appreciated.


These kinds of questions make me want to jam my head through the computer screen. I don’t get why there are women who are okay with being a dude’s sloppy seconds. I mean, how does that even remotely feel good inside? And T, that’s what I want you need to figure out. 

F-ck this dude for a second because the real problem is not how he’s treating you, it’s how you’re allowing yourself to be treated. Sure, he’s being a total prick tease for sending you mixed messages, but come on, you’re a big part of the feel-like-sh*t-puzzle. If you have ears, which I’m assuming you do, then there’s no way you haven’t gotten the message that he does not want to be with you. Like, he’s actually said it quite a few times now. Also, how is this someone you call your best friend? Jeezus, what the fu-k is going on here?

Look, I know it doesn’t feel good to be called out like this, but I really just need you to see what a pitiful situation you’re in because: a) you deserve someone who wants to be with you, b) you deserve someone who isn’t sleeping with another woman, c) you deserve someone who respects you and d) you deserve someone who doesn’t make you continuously fight for their affection. Seriously, this is not a lot to ask of another human being; in fact, it’s the bare minimum for any healthy relationship and T, you can't check off even one of those boxes with this guy.

So please, let the idea of whatever you think you have with him…..go. Stop letting him dick you around and peace out of this situation. In order for this to work though you’re going to have to put some major space and time between the two of you. It will be hard but trust me, it will be so worth it when you finally find a guy who actually gives more than two sh-ts about you.

Thanks for writing in and keep your LIFE + STYLE questions coming to [email protected].