Adapted from a recent online discussion.
Tiptoeing doesn't help: Talk frankly about life decisions
Non-ultimatum, ultimatum: I am in my mid-30s, and I've been in my current relationship for over a year. He says he sees us getting married, having kids, etc., but hasn't yet proposed and I'm getting antsy. How do I bring this up without issuing an ultimatum? I don't want to waste precious time in a relationship that isn't going anywhere, but at the same time, I don't want to push him into a proposal. Any words of wisdom?
Carolyn: Propose to him. If you're really ready for that, of course — meaning you're with someone who just feels right, and you have no reason to believe the foundation of that feeling will change.
If instead it's about your time of life and being faced with tough decisions (say, about whether to start trying to have a baby now, or wait to see if this relationship goes the traditional marriage-and-babies path), then I'd say just talk to him. Make it about facts: You want to have a baby the old-fashioned way, and your window of opportunity is closing, and while "over a year" isn't that long, you and he need to figure out whether the "he sees us getting married, having kids, etc." is abstract, or concrete.
I know this kind of frankness is famous for scaring people off, but what should be just as famous is the unhappy ending that comes when people tiptoe around the truth.
Usually, tiptoeing just postpones whatever unhappy ending is already in the works — which, again, is an unaffordable luxury to a woman in her mid-30s who wants to bear children.
While it's important to be frank, you do need to be careful not to demote your boyfriend to sperm bank. Steer it away from "I want babies, are you in?" and toward "I have choices to make, soon, and because I love you, I want to make those choices with you."
Moving on, hanging back are mutually exclusive
D.C.: How do I know if it's a bad idea to hang out casually with a very recent ex? He dumped me, and by "hang out" I mean meet for lunch or see a movie.
Carolyn: Dunno. What do you want out of it, besides lunch or a movie?
D.C. again: Dunno. I miss him and want the chance to be around him, I guess, but am worried it might keep me from moving on.
Carolyn: I think you worry astutely. If you were able to cite something specific and limited, a la "He's the only one I trust to advise me about my office politics" or "He understands my family, and I just had a bad visit with them, and it would make me feel better to talk about it with someone without having to fill in all the back story," then I'd say to try lunch and see how you feel afterward.
But just wanting to be back in his orbit again, for the sake of it, means your most pressing post-breakup job is to build a new life without him. Unless you find him miraculously unappealing, seeing him is likely to set your efforts to get over him back to where they began.