Ask Jono: Having "The Talk" With Your SO
There's this guy I like, and one day, out of the blue, he kissed me. Now, I assumed that was him trying to non verbally communicate that he liked me, but the next day he acted like nothing had ever happened. That is, except when no one else was around, when he would act like we were dating. As the situation evolved, we became friends with benefits. I really like him, and I want to take the next step with him, but I don't want him to think I'm being clingy, and I also don't want him to be afraid of commitment. How should I proceed?
My sleazeball sense is tingling. Not as badly as it was when I got this letter—that time it was pretty obvious, and now it's just a vague sense of unease. I'm not saying there's anything definitively sleazy here, and this guy might be a genuinely good dude, but a few things about his behavior concern me.
First, there's the FWB thing. I'm beginning to think that every time someone writes in about a friends-with-benefits relationship, I go "BOOOO" and bang a gavel. Not because such relationships never work (though in my experience they rarely last long), but because I'm suspicious when all a guy wants from you is to get all up in your biz, and otherwise wants nothing to do with you. Your guy's initial come-on, if you can even call it that, makes me raise my eyebrows with even more suspicion. (For the record, non-verbally communicating that you like someone generally means "smirking and winking," not "attacking your face with his mouth.")
But I'm also concerned by the fact that he seemed disinterested in you when other people were around. Again, this isn't too troubling on its own; it only worries me when considered alongside those other issues. The way I see it, there are two possibilities here: he's a shy dude who genuinely likes you but is too awkward to express that when you two are in mixed company, or he is Captain Sleazyman.
So my suggestion here is that you need to have some version of The Talk. I know that having The Talk is basically boy poison, and being asked "where is this relationship going" causes guys to clutch at their throats and then die, but I honestly can't tell what this guy's deal is, and you deserve to know. Here's how to broach the topic without scaring him off.
1.) Pick a good time to talk to him.
The absolute worst thing to do is to text him "we need to talk." Any approach where you send him a cryptic message and put him on edge is going to be a disaster. Instead, wait until you're both together, in person, feeling comfortable and happy. Trying to do this over the phone is a terrible idea, and trying it online or via texts, where you can't even read someone's mood through tone of voice, is even worse. On top of that, it's intermittent communication, and the waiting will only serve to drive you insane. ("He's taking too long to respond to my frantic, rambling text, so I guess I should text him '????' every 30 seconds until he replies!")
2.) Start very gradually.
You don't have to be like "Hello ARE YOU MY LITERAL BOYFRIEND." You can start by just trying to ease him into a more relationship-y relationship. I don't know exactly what your FWB situation involves, but if you want, for example, to go on real dates and become exclusive, just casually invite him to something with you that is not hot makeouts. Say something like, "Hey, I feel like going (bowling/to the zoo/to anything not super date-ish), we should do that!"If he's interested in you as a person, and enjoys being with you, and you two start doing a lot of datey things together, you've already developed this into a more serious relationship without having to have The Talk at all. At that point, the best outcome is for him to volunteer that he wants to be serious and exclusive, without you having to be ask. Of course, it doesn't always work that way, and you shouldn't wait around forever for him to declare his intentions. Sometimes you're going to need to sit down with him and figure out where this is going.
3.) Be clear but not confrontational.
If he's never interested in doing real things with you, then The Talk is necessary, but pleeeaase don't just run up to him and blurt out "So I feel like I don't know where this is going and what you want out of life and Jono (who is from the internet) has confused me and are we getting married??" The point here is not to put him on the spot so that you surprise him into admitting the truth, because dudes do not work that way. The point is just to figure out if he wants—or is ever going to want—more from you than just sexytimes. But don't just ask him some vague question like "Where is this going??" because a guy has no idea what that means. Say something like "I really like being with you, and I don't think I want to be with anyone else," and see how he responds. This is a delicate way of basically saying "I want us to be exclusive," but it doesn't demand an answer from him. It tells him what you want without sounding like an ultimatum.
I'm not going to lie here: there's always a chance that this will scare him off. But if it does, please don't fall to your knees in the pouring rain and look up at the sky and shout "Jonoooo!!" If a really subtle attempt to gauge his feelings like the one I just suggested makes him want to bail, then you don't want this guy anyway. No matter how munch fun you're having, staying in a relationship that never becomes as serious as you want wouldn't be fair to you. You deserve to be with someone who likes you the same way that you like him, and it is absolutely not "clingy" to want to know if a guy likes you, or just making out with you.