The Hook Up: How to take a casual relationship to the next level


I’ve been seeing this woman for a little over three months, having met her online. Until a few weeks ago, I actually wasn’t even sure she liked me as more than a friend. I knew I liked HER—she’s cute, smart, funny, creative, generous, introverted but outgoing, pretty terrific and I love hanging out with her—but I wasn’t sure the crushy feelings were mutual.

Well, over a glass of wine and a particularly brave (and uncharacteristic) move on my part, I told her I liked her in THAT way and she reciprocated. So here is where things stand now: We know we like each other, some physical intimacy has occurred, but other than that, things haven’t progressed much. We haven’t had a “to be or not to be exclusive” chat, we see each other maybe once a week, if that, and—I don’t know—am I just being insecure and rushing things? I’m just not sure how to proceed here, because I want us to be closer and to see her more often. But I also want to show I can be understanding of her busy schedule—I have one, too, after all—and I don’t want to freak her out by pushing things toward something she’s not ready for. It’s been a long time since I have felt this way about someone, though, but because it’s been a long time, I find myself feeling new at it.

Where should I go from here?

Anna says: With Kelsey, I had the “let’s be girlfriends already” talk by accident. We went out with a mutual friend one night and, after a few beers, he started casually referring to Kelsey as my girlfriend. I didn’t correct him. I barely even noticed actually. We sure acted like we were a couple, even though it was relatively early on in our relationship (somewhere around the one month marker, I’d wager). But Kelsey noticed, and she was—not thrilled. I mean, she was thrilled to be dating me, that was obvious, but “girlfriend” carries a lot of weight for some people, and she wasn’t ready to update her dating resumé without talking about it first.

And boy did we ever! Nothing makes me feel gayer than having an hours-long talk about what the word “girlfriend” means. Long story short, I convinced her to go steady with me and now our two hearts have become one flannel pajama-wearing, Netflixing unit. Hooray!

This isn’t to suggest you should stage some kind of third-party, girlfriend-name-dropping sneak attack. I also understand how hard it is to transition from casual to OMG LET’S TALK ABOUT ALL THE FEELINGS, especially if you’ve been out of the dating game for a while. I will say though that a lot of the insecurity and the freaking out and the over-thinking is probably mostly in your head. And it’s natural and normal to think we can ruin things by, like, suggesting they spend two nights a week with us! Odds are, though, it won’t. So you might as well ask for what you want and see how that goes.

How do you bring it up? Again, everyone varies. Some people prefer the bold, direct “Let us pair-bond!” approach (I’ve been watching a lot of documentaries about koalas). Others prefer a more indirect, subtle route, a la scheduling more dates so that you’re upping the amount of time you spend together. Do whatever seems more natural for you, but I would suggest that you broach things one conversation at a time, so it’s not as overwhelming, and so the relationship can progress at its own pace.

In terms of the actual talk, casual is key, and for this reason, I’ve found it helpful to use my friends as conversation fodder. For instance, “What do you think of Alex and Piper moving in together after four minutes?” could help spark a conversation you want to have about cohabitation. Celebrities also work in a pinch if your friends are boring or nuns. They’re pretty much always doing something weird, like becoming Scientologists or creating their own stripper diets.

Everyone’s different when it comes to personal space, boundaries, and how much time they want to spend with a partner versus time spent alone. Personally, I’m a human barnacle, so I wouldn’t work well with someone who made funnel cakes for a traveling circus, for instance. Wherever you both are in your lives and priorities, the end game is all about mutual acceptance and working together to find a balance.

The longer solution involves gaining a deeper understanding of what’s going on for you and for your lady friend, and then working out ways of meeting each of your needs together. This involves fun talks about fidelity, future goals, and whether you’ll be watching Breaking Bad or Orange Is the New Black tonight.

Above all, be yourself. Know what you want and what you don’t want, and be willing to communicate those desires to your date. It’s possible she wants to see you more too and is just waiting for your thumbs up. And if that fails, just invite me over and I’ll exclaim loudly what a cute couple you make. Good luck!