Tell Me About It: Setting a date that keeps shifting into the future

Question: My boyfriend and I, turning 30 and 28 soon, have been together for almost five years and living together for four. We have talked about marriage and having a family several times, and it is something we both want. We have gone ring shopping, and he's even asked my mother for her blessing. He is on board with starting a family once I reach my early 30s and, for religious reasons, I want to be married before having kids, so this marriage window is shrinking.

He has said several times that we will be engaged by X date, and I've watched said dates come and go and no proposal (the first of those dates happened almost two years ago). I love him dearly, trust him, know he's committed to me, and I am so excited about our future, but what is causing him to go back on his word?

Answer: Have you asked him that?

Question: I have. He doesn't really have an answer. He has said he doesn't like feeling pressure from others (family, friends), but that's not something either of us can really control. I have tried my best not to pressure him, either, because I know how much that bothers him.

Answer: This is where a certain population looks at the ceiling and thinks why why WHY does any woman still wait around for someone to propose? It's a valid question in general, though probably not here.

That's because there's a preemptive answer waiting for you if you state the gist of your question out loud. Try it: "A 30-year-old man says he hasn't proposed to me because his mommy and daddy are pressuring him."

Factually correct beneath the snark, no? And if so, does it move you to propose? (Besides - you'd scare him into witness protection.)

Break down what you're actually waiting for, and the outlook doesn't improve. As you see it, you're waiting for a proposal you've been assured is imminent, and with it the ring/vows/children sequence you expect it to set into motion, so seductively routine.

When you include all the details you've shared here, though, here's what's really in the package you so patiently await:

A man seriously lacking in emotional toughness;

Or who makes empty promises;

Or who shifts blame to other people when called to account;

Or who doesn't know his own mind;

Or who does know but can't or won't articulate and own his choices;

Or who could marry you tomorrow but makes excuses instead;

Or some combination of these.

Please look at these carefully. For you to be in this position, at least one has to be true.

Given your dedication to him, you presumably share a life that functions warmly day-to-day. That's important, and valuable.

But it's not everything, not when you're young and healthy and responsible for no one but yourselves and generally on the "before" side of any number of things hitting the fan. On the "after" side, that's when you're going to want someone who is emotionally resilient, good for his promises, accountable, self-aware, able to speak a difficult truth, and unflinchingly committed to you.

If you don't have that, then don't wait too much longer to switch to Plan B.