All said, a woman might reasonably fall to pieces if you wait to tell her you’re just looking to fool around until you've shared eight months of loosely-hooking-up-and-also-doing-lots-of-date-like-activities. Just like disclosing a lethal food allergy, the sooner and more clearly you alert her, the better. You don’t need to shout MY NAME IS ANTONIO AND I’M NOT LOOKING FOR ANYTHING SERIOUS over the music the night you meet a girl on the dance floor, or in the Lyft on the way back to her place to hook up. But if you guys are texting the day after said sexy times, that’s a good time to lay down what you’re interested in. Or, more accurately, what you’re not interested in. (If you are genuinely open to something more happening beyond the bedroom, but wouldn’t be bothered if this went no further than a couple meetings on your still-on-the-floor mattress, then you don’t need to spell that out.) If you can, talk about it before you start to go on date-like activities with her—"date-like" meaning anything that involves leaving your houses, or anything or that starts before 9 P.M.
If, however, you are opposed to/not ready for/otherwise uninterested in putting any effort into dating a person, let them know. Don’t treat it as a favor to her that you’re giving her a heads up. It’s not a favor; it’s simply the right thing to do. You don’t get extra points for being clear about what you want just because the rest of society’s daters are out there pulling bare minimum bullsh*t. Don’t start your sentence with anything resembling “Just to be fair to you…” or “I just thought you would want to know…” This isn’t about her, it’s about you. “I want to be upfront with you that I’m not looking to date right now,” is a good start. You can also follow up with something along the lines of “if you are looking for a relationship, and are no longer interested in hanging out, I understand, but I’m having a great time and would love to see you again.” Unfortunately “I’m just not looking to date right now” has been appropriated by people who are just trying to weasel their way out of a tense breakup talk, so that little addendum just lets her know that it’s not her, it really is you.
You can also start by asking her what she’s looking for. Try something along the lines of: “I’ve been having a lot of fun and I’m just wondering what you’re looking for out of this.” Let her know that you don’t need an answer immediately, but that you’d like to talk about it before this goes too far. Personally, I think this is a great conversation to have via text, since people are more likely to be honest via text and they can respond on their own timeline, once they’ve had a chance to put some thought into their answer.
Just be honest. Don’t tell someone that you might be into dating them and you want to “see where it goes” when you know you’re only in it for the bomb sex you guys have been having. Wishy-washy answers like “let’s play it by ear” are not as sneaky as you think. And when you do definitively break things off with her six months from now, only a few minutes after she asks if you want to be a plus one at her brother's wedding, she’s going to be rightfully pissed. Err on the side of a firm, clear answer. Even if you don’t know what “this” is between the two of you, have clear answers ready for when she asks you to define some boundaries. I think men are often afraid that if they say they’re open to a long-term relationship, they’re then stuck with the person they told that to. That’s not the case.
So bring it up for yourself. So that no one gets mad at you, sure, but also because it’s the right thing to do—because it makes the rest of dating someone or just sleeping with someone or seeing where this is going so much more enjoyable.
