What next?

How do you know when is it time to move a relationship to another level, and how do you bring it up?

By Cary Tennis
Published August 11, 2004 7:22PM (EDT)

Dear Cary,

When is it appropriate to inquire about a casual relationship moving further? I'm back in the dating scene at 30 after a failed marriage and with a little boy of my own at home, and "dating" seems so much more complicated and bound by rules than in my innocent, stoned younger days. I've been on my own for the last couple of years, learning the ropes and struggling with the burden of single parenthood. I have done my share of dinner dates and coffee breaks, but all essentially not "right," and I'm not all that desperate to find a mate or boyfriend and figure if I walk into someone I like bunches, that's great, but otherwise I'll be enjoying my life all the same.

But I'm a passionate person! My salvation is to remember all the rotten places I got myself into exploring those freedoms, the reasons behind erecting the caution signs. The tweeker husband I left in the dead of the night. The acknowledgment that anyone my age has their own recognized or unrecognized baggage, just a fact of life, right?

I've been seeing a fun guy for the last month or so and we have good times. No pressures of any sort, a riot in the sack, toys with the boy, cool dude. For once in my life I'm getting to know a person without going overboard right away. But what happens now? There've been no proclamations of love, no real assurances of exclusivity. I recognize his nonverbal gestures and am heartened and amazed at my capacity to sit on my hands, but at what point -- if ever -- should I wonder about direction?

Growing Up

Dear Growing Up,

It's natural to wonder what happens next, and to measure the progress of your feelings for each other. But one month is not very long. How about this: After you've been seeing him for six months, sit down and ask yourself how you like it. Do you really like it a lot? If you really like it a lot, why not tell him that? Just tell him that you've been seeing each other for six months now and you really like the way it's going, and ask him if he likes the way it's going as much as you do. You could just leave it at that. But then at nine months you might ask him again if he still likes it as much as you do. And at one year, if you're still enjoying seeing him, you might tell him that since you've now been together for one year, you consider it officially a serious relationship and it's time to talk about the future. Why not? A year sounds serious to me. Isn't a year serious? Nobody could say you're rushing things. Talking about the future doesn't mean that you demand any kind of promise or try to force him to commit to anything. It's more like just the intellectual realization that, duh, there is a future and you are kind of in it, and so why not acknowledge it, and talk about what may happen if you still keep doing this same thing for five or 10 years -- which it's possible to do quite easily if you don't break up. You know what I'm saying? Just talk about reality, that's all. Just talk about what you both know to be true.

During the next year, I would continue to explore it. And by the second anniversary of your being together, I think you would be within your rights to want some kind of security, to know what he wants to do, whether he wants to just be your boyfriend or whatever. I mean, it's a serious thing and you do have to make decisions. If he isn't ready to commit, it won't be the end of the world. Maybe you'd give him a year during which you begin to think about other men if you get the feeling he's not going to stick around.

I know that's all hypothetical, but I find it really does help to measure things, to think in quantitative terms. That doesn't reduce your passion or the chaotic intensity of life; it just gives you a template, a map, some milestones to acknowledge.

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Cary Tennis

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