How does my “friend with benefits” actually feel about me?

jillian asks: I’m a 16-year-old girl and I’m really confused about stuff with a guy right now. We have been best friends for years. We dated for a while, and then broke up so I could focus on myself, since I have personal problems going on. Well we decided to stay friends and started to get closer again. Right before spring break we were talking at school at our old “spot” and we started making out, and later on decided to be ‘friends with benefits.’ We started hanging out a bit more and doing stuff we used to do in our relationship. Then we took things further (and this was my first time) and it was nice and all. We both enjoyed it and I’ve been hanging with him and his family a lot more lately too. I told my friends about all this and they say we are always touchy and flirty, and now he’s started calling me cute all the time. Neither of us had feelings for one another but everyone thinks he likes me now, and I don’t know if he does or not. I don’t know how to tell if he likes me, or to tell if I like him again. I really don’t know what to do with this.

Hi jillian –



As dogs go, I understand human language better than most.  Some say maybe better than any other pooch.  But I do get confused by some words.  And one of them is “like.”


I like you.  I like just about everyone I meet.  I like tummy rubs (okay, no I really LOVE tummy rubs!).  I like fresh air and car rides and fire hydrants and flowers and the sound of old big band recordings.


But maybe it’s better to describe a person here.  My friend Handsome loves lots of things (including, best of all, me), but he likes far more.  He likes almost all music.  He likes anyone who returns his smile.  He likes most art.


Now I’m not trying to be silly here, but I’m really asking – this guy has been your best friend, your boyfriend, and now your friend-with-benefits, and you’re asking me if he likes you?  jillian, he’s absolutely nuts for you!  Whether he knows it or not!


By that I mean that teenage boys are very confused about a lot of things, and he might be enormously connected to you but still think his true love is Selena Gomez because he’s had a poster of her on his wall since he was six.  So he might not feel the degree that he really loves you.  But whether he does or not, he loves you, a lot!


In fact, the whole friends-with-benefits thing, to me, sounds like something for people to do who are scared to commit to each other.  And that can make a lot of sense.  Let’s say one or both of you is planning to move away after you finish high school.


The problem with that idea is that one can start to feel committed without having planned on it!


(And for that matter, having sex can result in a LOT of things happening that you’re not planning on!  If you aren’t fully practicing safe sex, please let me know and I’ll write you back some VERY important suggestions to help you stay trouble-free)


So my advice to you is to take the word “like” out of the conversation.  It’ll be too confusing.  Instead, you might tell him that you’re feeling very connected to him, and would like your relationship to be exclusive, that neither of you dates anyone else for now.  My guess is he’d be fine with that, but if not, it’s a very good conversation to have so neither of you gets too hurt.


Because, to sort-of quote that hit song from about twenty years ago… I don’t know much, but I know he likes you!


As do I!


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